In confident pursuit of that feeling, I’m thrilled to be joining Microsoft to run Design & Research for their Web Experiences organization.

I was Microsoft-adjacent 10 years ago at MSNBC.com in Building 25, but this will be my first time as a blue badge, so to speak. I’m also thrilled to be joining Liz Danzico and John Maeda, who have also started at Microsoft in the last several months. I’ve known them both for a long time and have wanted to work with them forever.

There are several things which drew me to this opportunity, but at the top of the list is the people. Not just Liz and John, but the thousands of teammates in Seattle, Vancouver, Hyderabad, Barcelona, Beijing, and many other cities. There are certainly some great solo efforts in tech, but almost all of the best work I’ve been around has been the result of getting the right people jammin’ with each other. In my first several days here, I’ve already met so many of those people, and I can’t wait to continue the momentum Albert Shum created by carrying the torch for one of the best Design & Research teams in the Pacific Northwest.

The second thing I’m super excited about is the scale of the work. I’ve worked on the largest sports site in the world and one of the largest social networks in the world, but the properties in this group reach well over a billion people. Between the (refreshingly fast!) Edge browser, MSN, Bing, and several other products, Microsoft has quietly built up one of the top five properties in the world in terms of traffic and reach. They’ve also done it with humility, knowing how far they are from being perfect. I also love that so many of these products can and will be so much more as we begin to use some of the technology that’s emerging within Microsoft. In my first two weeks, I’m already overflowing with ideas.

Finally, the other thing I’m most excited about is getting back into the office in a flexible hybrid environment. I’ve worked in-person for most of my career and remotely for the last four years, and where I’ve landed is that everyone’s preferences are different, and it’s just tradeoffs all the way down. Where you land depends on a mix of your personality, your life outside of work, and what type of job you have. For me personally, I very much like being around people and feel like I do better work when I am… but I also like getting back my commute time a couple of days a week and making daily jogging more convenient. Also, Henry (pictured above) enjoys the extra lap time. Microsoft’s hybrid policy is a nice balance, and it sounds like exactly the right setup for someone like me.

Speaking of the exactly right, this also feels — for me at least — like exactly the right time to join Microsoft. The company has been through several distinct eras over the decades, but this feels like the era of re-commitment to the planet. To customers delightful experiences, to employees a great environment, and to the natural world, a smaller and eventually negative carbon footprint.

It’s a new year, and I couldn’t be any more here for it!

I’ve been using Pinafore (along with a user stylesheet I created… feel free to grab it for yourself) to use Mastodon on the web, and a combination of Ivory and Metatext on my iPhone. Ivory looks a bit nicer but Metatext has a Notifications tab that acts more you’re used to it working on Twitter.

If you want to move all of your activity over wholesale, go to town. If, however, you want to keep publishing Tweets on Twitter and have them automatically publish to your Mastodon account as well, this short guide is for you. The entire process should take around five minutes. It’s mostly just clicking around on a couple of websites.

Important: If you do this, the goal should not be just replicate your Tweets and never visit or engage on Mastodon. The goal should be to help you build your Mastodon presence and save you from having to manually double-post. Ideally you quickly get to the point where Mastodon becomes your primary crib.

Step 1: Open a Mastodon account

If you’ve already done this, great. If you haven’t, head to any server you want — like mastodon.social, for instance — and set up your account. You can always switch your server (along with any followers you accrue) later, so don’t stress about the server you choose.

Step 2: Open an IFTTT account

IFTTT (“If This Then That”) is a freemium service that lets you automate things on the internet. You can use the free account for now. The only difference for our purposes is that the free account will only poll your Twitter account for new Tweets once an hour. This is only a problem if you Tweet a lot per hour because they will all get posted to Mastodon in batches, once an hour. If this becomes a problem, you can always upgrade to the paid version for two bucks a month. For now, head over to IFTTT.com and set up a free account for yourself.

Step 3: Get your Mastodon posting URL

Head over to your Mastodon account on the web and choose “Preferences” in the lower right corner. Then choose “Development” at the bottom of the left navigation. Then choose “New Application” in the upper right. Under “Application Name”, type in whatever you want… something like IFTTT. Under “Application website”, type in https://ifttt.com. Leave the “Redirect URI” field alone, and make sure *only* the write:statuses box is checked. Hit the Submit button at the bottom of the screen, and then click the name of your application (e.g. IFTTT) on the resulting screen. Now open a new tab in your browser, leaving this page available for later.

Step 4 (Final step!): Connect your IFTTT account to your Twitter and your Mastodon accounts

Head back over to IFTTT.com and hit the “Create” button in the upper right. Click the big “If This” button, search for “Twitter”, and then click it. Scroll down and choose “New Tweet by a specific user”. Choose your own Twitter account and IFTTT will perform the necessary authorization. Then, type the username to monitor (in this case, your own), and hit “Create Trigger”. Now click “Then That” and search for “Webhook”. There should be a tile on the resulting page that says “Make a web request”. Click that. You’re almost done. For the fields, enter the following:

URL:
https://mastodon.social/api/v1/statuses (replace “mastodon.social” if you chose a different server above)

Method:
POST

Content Type:
application/x-www-form-urlencoded

Additional Headers:
Authorization: Bearer AccessToken (replace the word “AccessToken” with the access token from the one on the Mastodon page you left open above)

Body:
status={{Text}} (Everything inside those brackets is the content of the Tweet… you could prepend some custom text right after the equals sign if you wanted)

Now hit the big “Create Action” button, then the “Continue” button, then the “Finish” button, and BOOM, you’re done!

The next time you Tweet, within an hour, it should appear on Mastodon. If you upgrade your IFTTT account, it should lag by only a few minutes.

I encourage you to move your primary posting and reading activity over to Mastodon, but this is a good baby step if you’re not quite ready for that yet. It’s also a great way to set up news bots. We need more of those. You can follow the Axios newsbot I created here, or you can follow me on Mastodon here.

As someone who competed against Figma for a couple of years, I want to talk briefly about what makes them so hard to catch, and why I think Adobe ultimately decided they would never beat them:

Performance.

Even though I have spent over 20 years in the design industry working directly on consumer products, I never fully appreciated the importance of performance until working in the design tools industry.

Most digital consumer products are used in short bursts over a long period of time. Think about the Amazon app on your phone. You open it maybe once a week, peck around for what you need, hit Buy Now, and you’re on your way. If there is a two-second lag between purchasing and getting your confirmation screen, you don’t even think twice about it. Even in the case of an outright error, you just shake your head, hit reload, and things are usually fixed.

With professional production tools though — whether design, engineering, or otherwise — full-time craftspeople spend almost every hour of every work-week inside of your software. Every time something goes even remotely astray, it is noticed. Putting aside catastrophic stuff like data loss, even things like cursor lag, screen flicker, progress bars, and scroll/zoom performance are tiny paper cuts that form into pools of blood by the end of each day.

Figma did a lot of things right over the ten (yes, ten!) years they’ve worked on the product, but one thing they did that no one else has been able to replicate is meet and in some cases exceed native app performance inside of a web browser.

Nothing Figma has accomplished in the marketplace would be possible without this, and it is the thing that competitors have struggled the hardest to replicate. When you build software using native code, you get a lot of stuff for free. Need a scrolling list? Apple, Microsoft, and Google have multiple pre-built components you can use. Need to draw one semi-transparent shape on top of another? The system already knows how to render that. Need to optimize it all for speed? Most of that work has already been done.

Inside of a browser though, the work is rarely done for you. Even in instances where someone has already built a component, it’s often too slow or glitchy to use in a professional development environment. So what did Figma do about this? Over the course of several years, they:

• Built their own components and architecture painstakingly from scratch and never settled for “good enough”
• Worked with organizations like WebKit and Chromium to improve web browsers themselves (the benefits of which go beyond Figma)
• Detailed out in the open what they were doing and how

It was this last one that really made me see how wide the moat was for the first time. Normally companies keep their secret sauce secret. After all, why would you want to give your competitors any information that might help them compete? But a company who routinely publishes information that is useful to competitors? That is some confident shit right there. It reminded me of a tweet I can’t find from several years ago:

“The design tool war is already over, but no one knows it yet.”

Fast forward a few years and everyone who has tried to match Figma’s all-around performance has fallen short. Private companies like Sketch and InVision. Public companies like Adobe. It’s not for lack of effort by hundreds of incredibly smart people. It’s just really frickin’ hard. Combine that with the fact that Figma is a moving target who is now building entirely new capabilities, and you can see why Adobe decided this wasn’t just a move they wanted to make… it was a move they had to make.

… which brings us back to a lot of the reaction we are seeing on Design Twitter today.

I don’t think people mind the abstract concept of Figma being acquired by another company nearly as much as they mind the very real threat of Figma losing what makes it so special in the first place: focusing maniacally on performance, thinking differently, and optimizing for user experience above all else. The backlash is an expression of how a lot of people feel Adobe has done in those categories over the last decade.

If I’m Adobe, I am printing out as many Tweets from today as I can, making a book out of them, and then doing this:

After that, I’m letting Figma lay the tracks for the next decade of this industry and rallying the thousands of talented people at my own company to rethink how the entire organization builds software. Within the next several years, it’s going to be possible to go from idea in the morning, to prototype in the afternoon, to working code in the evening… and the company who can do that most thoughtfully is going to be one of the most important companies in the world.

Players put their bodies on the line every day to a degree that most of them are not fairly compensated for, so I will almost always side with players in terms of wanting them to get the best deal possible. This is a unconventional idea to help achieve that goal and get both sides to a good and equitable place as quickly as possible.

The elevator pitch

Before the start of the 2020 NFL season, all 32 starting quarterbacks should initiate a quarterback-only strike. Everyone else shows up to work and gets paid. If there is no acceptable deal in place by opening week, the games begin, the quality of play degrades dramatically, ratings/attendance/sales tank, and owners — unable to wait out a group of 32 players with many millions more in financial security than 99% of the league — are forced back to the bargaining table with a 16-game season, a true 50/50 revenue split, and a few other things players are quite reasonably asking for.

Why it will work

Athletes get out-negotiated by owners for a very simple reason: there are 32 owners and none of them ever need another paycheck again. Losing even vast amounts of their fortunes will not degrade their quality of life. There are 1696 active NFL players and most of them are materially affected every time they miss even a single game check. 32 billionaires vs over a thousand normal people who need paychecks is a recipe for exactly the sort of terrible deal that was signed ten years ago and threatens to be signed again. The goal of a Quarterback-Only Strike is to change the equation to 32 billionaires vs 32 of the most popular cash-rich players.

Do quarterbacks really have that much cash cushion? Let’s take a look at lifetime earnings for the 32 starting quarterbacks in the league right now. Note that this doesn’t even include endorsements, but also doesn’t include taxes:

1. Drew Brees: $244m
2. Tom Brady: $235m
3. Rodgers: $233m
4. Roethlisberger: $232m
5. Ryan: $223m
6. Rivers: $218
7. Stafford: $210m
8. Newton: $121m
9. Wilson: $109m
10. Cousins: $100m
11. Dalton: $83m
12. Tannehill: $77m
13. Carr: $72m
14. Garoppolo: $64m
15. Fitzpatrick: $63m
16. Foles: $62m
17. Goff: $49m
18. Winston: $46m
19. Wentz: $39m
20. Trubisky: $24m
21. Mayfield: $24m
22. Murray: $24m
23. Darnold: $22m
24. Brissett: $17m
25. Jones: $17m
26. Allen: $15m
27. Mahomes: $13m
28. Watson: $11m
29. Haskins: $9m
30. Jackson: $6m
31. Prescott: $5m
32. Lock: $4m

I have no idea how these guys invest or spend their money, but in my estimation, until you get down to the final few players (especially Dak… sorry Dak!), you are looking at pretty good financial cushions. Certainly enough to weather a few games or an entire season… especially if you include lost backpay in your deal requirements. Most position players in the league cannot afford this sort of holdout, but pretty much all starting QBs can.

It’s also possible that other players who have lifetime earnings over, say $25m, decide to join this strike in solidarity, but it’s not strictly necessary. Some marquee names might include J.J. Watt ($85m), Richard Sherman ($69m), or the NFL’s top selling non-QB jersey title holder Odell Beckham Jr. ($48m).

The other thing that’s nice about this proposal is that it’s literally the only position in any sport that could pull it off. Football could easily weather a strike at any other position, but not quarterback. Baseball could weather a strike from any position — even pitchers. Fans love offense! Basketball could weather a strike from any position because superstars are spread out amongst all five positions. I don’t watch a lot of hockey or soccer so I will just assume they fit my narrative too. ¯\_(ツ)_/¯

Quarterbacks are almost always the face of the franchise, the entire game runs through them in today’s pass-heavy NFL, and this is the perfect time to consolidate that power against owners and use it to improve conditions for the other 1664 players who don’t hold the same cards they do.

When I initially came up with this cockamamie scheme a few months ago, the reason I thought it might not work is that of all players on an NFL team, you would think quarterbacks would be the coziest with owners. But now that I see my own team’s QB, Russell Wilson, along with Aaron Rodgers, come out as strongly against the current CBA proposal, I think this thing could have some legs.

In conclusion

If players cannot get the very best deal they deserve this offseason, a Quarterback-Only Strike should be actively considered because it changes the negotiation from 32 vs 1696 to 32 vs 32. Additionally, you only need a majority of owners to cave, so if a few owners are insulated by the fact that they don’t have star quarterbacks yet, the rest of the owners are still vulnerable.

It’s also entirely possible someone else has already thought of this and kicked enough holes in it to show why it wouldn’t work. Basically, I need some more eyes on this thing. Agents, players, sports attorneys, whoever. If you know of someone who you think would have an opinion about it, I’d love to hear from them. The comment section is open below.

First, let’s dispense with the easy part: despite what you may read on Twitter, remote work is neither the greatest thing in the world nor the worst. We are not moving to a world where offices go completely away, nor are we going through some sort of phase where remote work will eventually prove to be a giant waste of time. In other words, it’s complicated.

The way to look at remote work is that it’s a series of tradeoffs. You enjoy benefits in exchange for disadvantages. The uptake of remote work over the next decade will depend most on the minimization of those disadvantages rather than the maximization of the benefits. Reason being, the benefits are already substantial while many of the disadvantages will be lessened over time with technology and process improvements.

Instead of writing about the advantages and disadvantages separately, I’m going to cover several aspects of remote work and discuss the tradeoffs involved with each.

Work Overhead

There is a certain amount of “overhead” involved in having an office job. You usually need to wake up at least an hour or two before the workday begins, put yourself together (often a much more arduous process for women because of the gender-specific norms we’ve set up), commute to work, and any number of other things involved in just getting to your desk every day. Then, when the day is over, you often do the same thing in reverse. To make things easy, let’s call this 90 minutes on each end. That’s an extra 15 hours a week! For reference, there are days when I wake up 10 minutes before my first meeting of the day and it’s no problem at all.

Lopping that 15 hours off is probably the part of remote work that is the most unconditionally positive. You could try and rationalize your commute by saying it’s when you catch up on all of your great podcasts or whatever, but you don’t need an actual commute to do that. You could spend that time in the morning on a walk and then go for a run in the evening and it would be a lot healthier.

Math-wise, if you assume that most employers do not consider overhead time as part of the ~40 hours you’re getting paid for, working remotely can reduce your true work week by about 27%. If you already work remotely and you were to consider taking a traditional job again, you’d be agreeing to a whopping 37.5% longer week!

Anecdotally, I’ve heard that some people actually do miss their commutes and in some cases have set up “fake commutes” for themselves. They’ll wake up, drive 5 minutes to the coffee shop for an espresso, and then drive back. I do this occasionally, but it’s just for the coffee.

Daily Habitat

The advantages of remote work get less clear when you evaluate your “daily habitat”. If you compare a Google office, for instance — full of perks like on-site massage therapists, crepe stations, and basketball courts — to a tiny apartment shared with two roommates and a screaming baby, I bet most people would choose the Google office. On the other extreme though, what if you compare a cramped office with poor ergonomics and bad lighting with a comfortable home on a ranch with alpacas and a nice fish pond out back? In other words, there are a wide range of variables that will determine whether your home office habitat is more enjoyable than an office would be.

If you asked me “would the average tech worker living in San Francisco prefer to work from home, in San Francisco” I would probably say no, due to the combination of office perks and small living quarters. If you asked me the same question but for Denver, I might say yes. We have a lot of people at InVision who have traded cramped, overpriced apartments in tech hubs for more comfortable situations across the country and the world. This seems like it will be a common outcome in the near future.

So… in order to answer the question of whether you’d like office life better than home office life, you need to ask “what is the office like” and “what would my home office be like”?

On the question of how optimal your home office would be, I can’t really say I’ve nailed this yet, much to the chagrin of my wife. I take video calls from all around the house, and I can see how that would be highly inconvenient for everyone else in the house. If your work activity is limited to one room, the rest of the house remains off-microphone and off-camera. I need to get better at this and stop taking so many meetings from the living room couch.

InVision also issues everyone $100 auto-refilled coffee cards every month to encourage people to change up their surroundings frequently. While I take advantage of this once or twice a week, I also don’t want to be the person in the coffee shop loudly conducting their business in public every day.

Meetings

The aspect of remote work I was probably least excited about was video meetings. I’ve never been big on video calls in general (even personal ones), and all of the video conferencing I’ve done in the past has been rocky. Flaky connections, unwieldy software, and uneven power dynamics have generally made for a poor experience.

Happily, however, internet connections have gotten more reliable, and with Zoom, the software is pretty good now too. As for the power dynamics, that’s where working at an all-remote company has helped tremendously. Instead of 9 people in a room together, reading each other’s body language, and one person halfway across the world stuck behind a screen, everyone is in the same boat. It’s a nice equalizer. In fact, during one conversation we were having around inclusion, a couple of people cited videoconferencing as one of the big reasons they felt more empowered in meetings. Since everyone is just a postage stamp sized video on everyone else’s screen, there is very little raising of voices or aggressive body language. It’s harder for one or two people to dominate conversations this way. It’s a rare instance of a technology’s shortcomings providing an accidental benefit.

I will say this about video meetings though: I have a very hard and sudden limit I reach with them. My first hour or two of video meetings every day are a joy. But the days when I have to do 4 or 5 hours on Zoom, it gets tedious. This is not the case for me with in-person meetings. I feel like in an office full of people you genuinely enjoy, sitting down in a conference room or taking a walk with them is refreshing. It’s part of what makes office life enjoyable… for me at least!

I think the evolution and improvement of video meetings — especially in remote work situations — is going to be a huge lever in pushing companies towards more remote work over the next decade. Although video meetings aren’t nearly as bad as they once were, there is a LONG way to go here. I’m sure in the next several years, we’ll see things like three-dimensional holograms and other stuff that will blow our minds.

One other thing about meetings in remote companies: working remotely has made me realize how unimportant and ritualized so many meetings are. Often times, I will get 90% of the way through scheduling a meeting in Google Calendar only to ask myself “can’t we just update each other on this project throughout the week via Slack?” Even staff meetings seem unnecessary sometimes.

Countries and Time Zones

One of my favorite things about working at an entirely remote company is interacting with people from entirely different cultures every day. Over the past year, my team has included people from Washington, California, Pennsylvania, North Carolina, Israel, Colorado, New Jersey, Australia, Spain, England, Mexico, Germany, and the Fake Washington… and that’s just my direct team. The rest of the company employs people from almost every continent. Although we are all still subject to our natural bubbles associated with tech work, it’s great to work with people outside your culture on a daily basis. We even have an ordained rabbi on our team, who leads our education programs!

There are challenges with hiring and getting hired internationally though. The first is local employment laws. It’s much easier to hire people in a country if you’ve officially set up a corporate entity there. That’s a bit of work. Even if you’ve set up an entity, it’s also a bunch of work making sure you are in compliance with local laws because they differ so greatly across the world. As a small example, even though we have an unlimited vacation policy that doesn’t require documentation in the United States, there are some countries where employees must enter all time off requests into a system; not because we want them to, just because laws require it. It’s a bit easier to hire people on contract in countries where you don’t have an entity set up, but there are downsides to that too. The bottom line is: even in all-remote global companies, it’s going to be easier to employ people in some countries than others.

Time zones are another challenge, and it’s almost all downside there. The simplest rule of thumb is that the further away people are, the more challenging it’s going to be to coordinate with them. I would consider our “fairly convenient time zones” to be everything from PDT to GMT. Anything outside of that and you are getting into territory where people may need to shift their work days a bit in order to accommodate the rest of the company. For instance, the person on my team who works from Israel actually time-shifts his day so that he works from 4pm to about 12 or 1am (local time), and that’s the way he likes it. He spends the first half of his waking hours with his family and the last half at work. Kind of a swing shift. It’s also doubly hard for people in managerial roles to be outside of core time zones.

Connection to Teammates

It’s a privileged thing to be able to say, but almost everywhere I’ve worked as an adult, I’ve felt a strong connection to my teammates. When you are fortunate enough to work in a field that you love, in an industry that’s booming, around people who share similar goals as you, you can’t help but feel like you have a second family at times. I know there are a lot of people who say the whole family metaphor of work is wrong and exploitative, but I believe in it in some situations. While I do believe that an employer can attempt to trick you into thinking you’re family in order to keep you loyal, I’ve also been in plenty of situations where my team DID in fact act like a family; looking out and sacrificing for each other, spending time with one another outside of work, and just generally helping each other through a lot of tough shit.

While it may not be “family” in the genetic sense of the word, going on stressful missions with people is bonding in a very similar sense. Every win and every loss brings you closer. I feel a sense of closeness with my old team at Twitter, for instance, that I’ve never felt with most other people in my life.

While I love the ~800 people I work remotely with at InVision, it feels different than what I’ve experienced in the past. On the one hand, I am in awe that I get to work with amazing people from Australia, Europe, Africa, Asia, and both Americas every day; people who I would never have even met if the company was headquartered in Seattle or San Francisco. But on the other hand, I’m only interacting with two-dimensional electronic representations of them on a daily basis.

Once a year, the entire company gets together for a week and it’s fantastic to see everyone in-person. In addition to that, between smaller team get-togethers and one-off work trips that I take, I probably see at least one teammate a month… sometimes many more.

I’m able to cope with having predominantly digital relationships during the day because I have a healthy social life outside of work, but if I didn’t, it might be rough. A lot of people look to office life for a good percentage of their real human interaction every day, and if you’re one of those people, I could see remote life being not fun at all.

Even though we have tools like Slack to help us keep up with what all of our teammates are doing, it’s different than being in a building together. It’s better the more independently you can work, but it’s worse if you need to be in communication with teammates for most of the day.

Importantly, this is also one of the reasons why it’s risky hiring junior people into remote roles. We tend to hire the most experienced people we can find, because in a remote company, you have to be able to paddle your own boat most of the time.

I do worry that if it is true, it may have a negative effect on our ability to coach up the next generation of designers, engineers, and other knowledge workers. In other words, a world in which every company works 100% remotely is probably a world which is less hospitable to people just starting out. There is no substitute for in-person tutelage.

Productivity

I’ve spent a long time thinking about whether remote work is more or less productive than in-person work, and I can’t say I know for sure either way. The complete answer is probably “it depends”, but my gut is that remote work is probably “almost” as productive as in-person work, hour-for-hour. In some cases, it may be 50% as productive and in other cases, it might be 200%, but if you told me the average was like 90%, I’d believe you. This number, however, is based on if you had the same group of people in one room together vs. across the world. Part of the beauty of remote work is that you have access to people you’d never have access to if you required they live in a certain city.

Let’s say, for instance, that you wanted to start a tech company in Lebanon, Kansas — the geographic center of the contiguous United States. You’d be hard pressed to find 20 A+ designers, engineers, and other employees crucial to your success (sorry Lebanon, nothing against you!). If you started your company in Lebanon and hired remotely though, you could hire top talent from all around the world.

This has interesting implications for SF and other tech hubs vs. the world. People in SF would tell you they would still have the talent advantage over you because they can hire A+ talent AND co-locate everyone together. This may be true right now, but a) it’s very expensive, and b) it may not be as true in the future when living in SF becomes even more cramped than it already is.

In terms of being super-productive in remote environments, the biggest lever is to work as asynchronously as possible. Carve off large chunks of work that you can do on your own without having to check in every hour or even every day. For design reviews, do some of them over video, but collect as much feedback via asynchronous comments as you can.

I’ve spoken with several startups over the last few months who are trying to make remote work more productive, so I expect a lot of innovation here shortly. I’ve begun using Navigator to help with my meetings, but there’s a lot more that will be done in this space.

Tools

The thing that has taken the most getting used to at an all-remote company is all of the communication that gets done over Slack. To be perfectly honest, I am not sure if Slack has made me more or less productive. It is likely that it has had effects in both directions.

On the positive side, it’s a very well-designed product for what it does and it makes non-face-to-face communication a snap. If you want to have a sporadic conversation with multiple people over the course of hours, it’s great for that. If you want to chat quickly with someone, it’s also great for that. If you want to broadcast interesting things to channels that the whole company can view and participate in, it’s great for that too.

On the negative side, it does feel like a second inbox to me. It also feels like an excuse not to document decisions properly. One of my least favorite workflows in Slack is:

1. Chat with Sara, David, Rachel, and Frank about something for awhile.
2. Make a decision at some point and stop chatting.
3. Wake up days or weeks later and wonder what became of that thing you were talking about.

Did the thing actually get done? Did you have an action item? Where is that conversation again? Was it with Sara, David, and Rachel? Or David, Rachel, and Frank?

I think Slack as a tool has the same core problem that Twitter has: it’s too easy to use it in a way that isn’t helpful. I think Slack has done a good job of trying to lightly push you in healthy directions, but I still haven’t had the aha moment where I couldn’t imagine my life without it. Often I do imagine my life without it, in fact.

To Slack’s credit, I think they provide a service that is so flexible that it’s really up to you and your company to use it in a way that adds the most value. I think if you visited the company with the worst Slack hygiene in the world, you would be appalled, but if you visited the company with the best Slack hygiene in the world, you would be beyond amazed. Stripe, for instance, maintains good hygiene by automatically deleting all Slack messages older than, I believe, six weeks. I really like this policy. It forces you to use Slack as a conversation medium and not a system of record.

Happiness

The two things you want most in a job are impact and happiness. While I’m very happy myself, I can absolutely see why remote work is not for everyone. Building on the aspects above, the three factors I think would most determine happiness are:

• The qualities of your home-office habitat.
• The qualities of your company’s office habitat.
• What sort of human interaction you want/need from co-workers on a daily basis.

You probably need at least two of those things to fall in your favor to enjoy your chosen path. Additionally, all three could change at any time, and the second one is very dependent on what company you’re talking about.

I think another important factor in determining happiness is how hard of a line you want between work and home life. One benefit of traditional office environments is that when you physically leave the office, it’s not too hard to flip the switch and go into “home mode”. Sure you may have to deal with the odd email every now and then, but it’s relatively straightforward to set up the work/home boundary. In remote life, it’s not always as easy. Personally, I am ok with this, as I would happily trade several hours of evening or weekend work for the ability to take off and go on a two-hour run in the middle of the day if I don’t have any meetings.

What’s Next

Whether individuals are better suited for co-located or remote work, one thing that seems like a happy medium is offering employees the ability to work from home a lot more often. For instance, a workweek that included Mondays and Fridays as home days and Tuesdays, Wednesdays, and Thursdays as office days would be fantastic. You’d get the benefit of everyone being available for face-to-face time three days in a row, but you’d also reduce commutes and potentially lengthen weekends. A lot of companies are already doing this for one day a week, but in many cases, two would be even better.

While hybrid setups like this will become more popular, it’s also pretty clear that more companies will try the all-remote route. In addition to advancements in collaboration and telepresence technologies, I imagine there will be entire companies set up around helping organizations work remotely. I could see something like Stripe Atlas addressing this opportunity directly. Just enabling companies to pay employees across many different countries is an entire company in itself.

I also wonder what other innovations we will see in co-working spaces. Although InVision offers co-working space in several cities, I don’t make use of it myself, so my experience with them is limited. I’ve talked to people who love co-working spaces and also people who hate them. Seems like there’s a big opportunity to create more cross-pollination between companies in the same co-working space. One of the surest ways to dream up new ideas is to mix with people who are nothing like you, and co-working spaces of the future could be one such way of doing just that.

Finally, I’m excited for more best practices to emerge around remote work. I still feel like we are all casting about in the dark a bit. We’re making it work, but are we as efficient and effective as we could be? Surely not. I haven’t gotten a chance to dig into 37Signals’ “Shape Up” yet, but I’m thinking something like that but specifically geared around collaborating remotely. Someone will write the book on this, and it will do extremely well. Additionally, it will need to be updated every year because of how swiftly remote work is progressing.

It’s been an exciting year learning to work in this new, distributed way. I can’t say for sure that I’ll be working 100% remotely for the rest of my life, but it does seem difficult to imagine going completely back to full-time office life.

It took an article I almost didn’t publish and tens of thousands of people saying they were creeped out, but Superhuman admitted they were wrong and reduced the danger that their surveillance pixels introduce. Good on Rahul Vohra and team for that.

I will say, however, that I’m a little surprised how quickly some people are rolling over and giving Superhuman credit for fixing a problem that they didn’t actually fix. From tech press articles implying that the company quickly closed all of its privacy issues, to friends sending me nice notes, I don’t think people are paying close enough attention here. This is not “Mission Accomplished” for ethical product design or privacy — at all.

I noticed two people — Walt Mossberg and Josh Constine — who spoke out immediately with the exact thoughts I had in my head.

1/ This is a good *first* step. Better than doing nothing. But it’s not enough. I read the full blog post. It makes no mention of disabling tracking how *often* the recipient opens the email. It’s also full of the rationalization that secret tracking is ok in “business” software. https://t.co/c0PbCRLgdp

— Walt Mossberg (@waltmossberg) July 3, 2019

I appreciate Superhuman’s changes, but the problem is recipients don’t know they’re tracked, and it’s still not going to warn them https://t.co/GPfUYVkBMs

— Josh Constine (@JoshConstine) July 3, 2019

Let’s take a look at how Superhuman explains their changes. Rahul correctly lays out four of the criticisms leveled at Superhuman’s read receipts:

1. “Location data could be used in nefarious ways.”
2. “Read statuses are on by default.”
3. “Recipients of emails cannot opt out.”
4. “Superhuman users cannot disable remote image loading.”

However, he also omits the core criticism: Recipients of Superhuman emails do not know their actions are being tracked or sent back to senders.

Rahul then details the five ways they plan to address those concerns:

1. “We have stopped logging location information for new email, effective immediately.”
2. “We are releasing new app versions today that no longer show location information.”
3. “We are deleting all historical location data from our apps.”
4. “We are keeping the read status feature, but turning it off by default. Users who want it will have to explicitly turn it on.”
5. “We are prioritizing building an option to disable remote image loading.”

The first three apply only to the first criticism about location, but fine. All good moves. Bravo.

The fourth addresses the concern about teaching customers to surveil by default but also establishes that Superhuman is keeping the feature working almost exactly as-is, with the exception of not collecting or displaying actual locations. I’ve spoken with several people about how they interpreted Rahul’s post on this particular detail. Some believed the whole log of timestamped read events was going away and were happy about that. Others read it the way Walt, Josh, and I did: you can still see exactly when and how many times someone has opened your email, complete with multiple timestamps — you just can’t see the location anymore. That, to me, is not sufficient. “A little less creepy” is still creepy.

Also worth noting, “turning receipts off by default” does nothing to educate customers about the undisclosed surveillance they are enabling if they flip that switch. If they’ve used read receipts at all in the past, they will probably assume it works just like Outlook. At the very least, Superhuman should display a message when you flip that switch saying something like “by turning on Read Receipts, you are monitoring your recipients’ actions without their knowledge or permission. Are you sure you want to do this?”

Rahul’s fifth and final fix is also good in that they now realize pixel spying is a threat that they need to protect their own users from. This introduces a moral paradox, however: if the technology you are using on others is something you need to protect your own users from, then why are you using it on others in the first place? These are all questions I’ve asked Rahul publicly in this series of tweets, which I’m still waiting for a response on, four days later:

Thanks for responding, @rahulvohra. I appreciate that you apologized and not in a “sorry *if* you were offended” sort of way. Before I respond, I have a few questions though.

#1: I couldn’t tell from the post if you are still collecting and reporting a log of timestamped (more) https://t.co/oQG5UH8uOE

— Mike Davidson (@mikeindustries) July 3, 2019

Ask yourself, even under this new system, whether you would ever not feel creeped out by someone saying:

“I’ve noticed you’ve opened my email four times, including last night, and even five minutes ago… and you haven’t responded yet.”

What if someone in your family said that? What if your ex said that? What if someone who had threatened you in the past said that? How about someone you didn’t even know? How about your boss?

It would be creepy enough for someone to actually say that to you, but even if they kept their mouth shut, they still know when you are looking at their email, and you don’t even know that they know. All because of these tracking pixels, which Superhuman has decided to continue using.

The message that sender-controlled read receipts send is “I’m watching you, I’ve been watching you, and you didn’t even know it”. Can you imagine ever saying that to someone, in any context, and having it go well?

I cannot. And the reason is that it communicates not only that you don’t trust me, but that I (the recipient) can’t trust you. It also implies that I’m doing something wrong by not emailing you back. As Ray Ozzie says, mess with people’s expectations at your own risk:

As early as Fernando Flores's Coordinator, we learned to view email as the distributed implementation of a very specific set of social contracts.

Once any social tool is ubiquitously-embraced, breach those contracts at your peril & the community's peril.https://t.co/dyV1oyLbFm

— ray ozzie (@rozzie) July 3, 2019

“I’m always watching you” is exactly the expectation that sender-controlled read receipts set. It’s how they work. And it’s the reason people don’t (and likely won’t) disclose that they’re using them.

Above all else, I want to know if people feel safe with this implementation. It doesn’t matter if I feel safe or if Rahul feels safe. Do women feel safe? Do people who have been creeped on over work email feel safe? Do people who have been harassed by salespeople feel safe? These are questions I would love for Rahul and team to investigate. You can probably start with someone like Cindy Southworth (hat tip: @amac) or many of the women, like Tracy Chou, who chimed in on the thread:

my summary of this is essentially: wow, fuck this flagrant violation of my privacy. https://t.co/VL10ySzotS

— Tracy Chou (@triketora) July 2, 2019

To Superhuman’s tremendous credit, they appear to have a pretty diverse team. Out of 30 people, I count 10 women and a variety of ethnicities. In Bay Area tech, that usually takes intentionality. Well done on that. It’s hard to believe, then, that not a single person — employee or customer — ever brought up how creepy the display of timestamps and read statuses are. Maybe someone internally did but the culture was not psychologically safe enough to bring it up and advocate against it. I’m just speculating. I don’t actually know. As Derek Powazek said:

In all those funders, engineers, designers, coders … NO ONE ever expressed surprise that the sender of an email could see a location every time a recipient opened it? When they were implementing it, no one said anything? Ever? I just don’t believe it.

— Derek Powazek (@fraying) July 4, 2019

Turns out, there seems to have been plenty of feedback, at least as far back as October 2018. Here is a Tweet from Elies Campo, formerly of WhatsApp and now working at Telegram (both known for their attention to privacy):

Last October I barely made it past @Superhuman’s onboarding & cancelled shortly after. I was shocked about their tracking & privacy values. I sent them feedback about the tracking features. They replied that they where considering a “stealth mode” . https://t.co/JzwijG5VYd pic.twitter.com/Qtak7t3k3d

— Elies Campo (@elies) July 5, 2019

Read the words from Superhuman “Delight Team” employee Cameron Wiese. He says explicitly says “I agree” and says he thinks Superhuman should turn images off to avoid triggering read receipts and “having your privacy violated”.

Cameron is no longer at the company. I have no reason to believe that is related to this, but it’s proof that Superhuman’s own very small team knew about this a long time ago and decided to do nothing about it.

I began to wonder why, so I started reading up on Rahul. I haven’t followed his career so I wanted to read some things he’d written or said to get a better picture of how he thinks about products. The first thing I came across was this article entitled How Superhuman Built an Engine to Find Product/Market Fit. It’s really well-written and full of a lot of great wisdom from Rahul that can help other entrepreneurs. Stuff I have never thought about for sure. In particular, the bit about zeroing in on the question “how disappointed would you be if you could no longer use this product” is great. It’s kind of an inverse NPS. Really good stuff. There’s one part of the article that may, however, reveal what led to this situation Superhuman now finds itself in: Rahul talks about how he explicitly ignores feedback from people who don’t already love his product. You can read it yourself inside that article or listen to it from his own voice in this interview at the 17:50 mark. Please get the full context from the material provided, but here’s the quote:

“You take the users who most love your product and turn those into an HXC (high-expectation customer), and you use those to narrow the market. And what I mean by that is, deliberately ignore the responses from customers who don’t fit that archetype of people who love your product.”

Bingo.

There is already a huge survivorship bias problem whenever you survey existing customers (which is why people like Elies and me aren’t even represented in these surveys), but doing things the way Rahul describes is like some sort of “devotional bias” on top of the existing survivorship bias.

I will say this: if you were skeptical of Superhuman’s commitment to privacy and safety after reading the last article, you should probably be even more skeptical after these changes. The company’s efforts demonstrate a desire to tamp down liability and damage to their brand, but they do not show an understanding of the core problem: you should not build software that surreptitiously collects data on people in a way that would surprise and frighten them. Superhuman needs to realize that the people their customers send emails to aren’t “externalities”. They are people. And they deserve not to be spied on by software they don’t even know about and never signed up to use. This was an opportunity for Superhuman to internalize what it means to respect privacy, and model behavior for the next generation of companies by doing just that. Instead, they have done little more than the minimum.

I want to quickly detour into a few other issues unearthed by the conversation last week, and then we’ll get back to Superhuman.

First and foremost, it’s important to understand how dissatisfying it is that I happen to be the one who was able to break through on this issue. I am not the internet’s ombudsman or a beacon of morality. For that, I would turn to someone like danah boyd or Anil Dash, who are always a step ahead in thinking about unintended consequences of technology. Second, to my knowledge, I have never been stalked or abused. I am not a victim speaking out. I’m just another white guy of moderately impeachable character who got on my privileged soapbox and said something.

There are several reasons I was able to do this:

• Because of my background and the way I look, I don’t have to worry about getting discredited or blackballed.
• Despite tweeting stuff like this, I have a decent size following on Twitter.
• I got extremely lucky twice in tech, so I’m secure enough financially and career-wise to where I don’t have to give a shit what the technology and venture capital world think of me.
• I haven’t personally wielded the sort of granular tracking technology I am railing against.
• I took the time to write a proper argument in long-form, litigating issues and not people.

Without all five of those things aligning, I think this whole thing wouldn’t have registered a blip. Furthermore, the first four of those things are about who I am and not what I wrote. Think about how frustrating this is for all of the people in the world who have something important they want to bring to light but are only able to do number five. This happens every day, and we miss a lot of it.

Conversely, I will also say that there are a lot of people in the world who have either all or some of the first four taken care of and instead take the easy route by tweeting out some thought-terminating-cliches (hat tip: Kristy Tillman), and then moving on to the next thing they feel like tweeting. If you have an argument to make, put in the work.

Along these lines, it’s been interesting to see who has reacted (and how) to my original article. If you search for who has linked to it on Twitter, you have to scroll through more than 50 posts before you find a single detractor. I didn’t research any further, and I could be biased by how Twitter displays search results, but my gut is that this is at least a 95%/5% situation, if not higher. To anyone who thinks “everyone knows this stuff is going on”, this is a death blow to that theory. “Everyone” in ad tech might know about email surveillance, but the great majority of people in the world do not… and those are the people you are either signing up to be honest with or signing up to deceive. As Upton Sinclair said:

“It is difficult to get a man to understand something, when his salary depends on his not understanding it.”

In this case, the statement refers to getting people who surreptitiously track others to understand that those being tracked do not know they are being tracked nor want to be tracked and that it is a violation of their privacy.

It’s also been interesting to see who has not weighed in. That includes a lot of people on both sides of this issue, including most of Superhuman’s VCs and 120 well-placed angel investors. I have, however, gotten DMs from some very prominent people in the investment community expressing solidarity but unwilling to say anything publicly. I’ve also gotten similar messages from people involved in the creation of Outlook and other tools that have had to wrangle these sorts of issues. I’ve also heard from entrepreneurs who have been specifically told by investors not to engage in discussions like these because it may limit their ability to fundraise in the future.

To those who have spoken out publicly or messaged me privately, thank you!

Conversely, there are also probably people on the other side of the issue who haven’t spoken up because they don’t want to look like jerks. This issue can really make you look like a jerk quite easily, so it’s sometimes easier to just let everyone else tell on themselves instead, like this guy from Founders Fund:

Exactly the caring, benevolent way the venture capital world would love to be represented, I’m sure.

While we’re on the topic of Twitter, I should mention that I’m generally not a fan of having public, free-for-all debates about heated subjects on the platform. I think the format often turns us into the worst versions of ourselves, expelling incomplete thoughts in such staccato bursts that we are often talking past each other and to the larger audience we are trying to impress. Twitter at its best exposes us to wonderful things we’ve never seen before. But Twitter at its worst is just bad performance art. I feel bad that Rahul and team had to absorb the tens of thousands of Tweets directed at them last week. But at the same time, I also feel like they had advance warning several months ago from myself and surely others that what Superhuman is doing is not right.

Being on the inside of this whole clandestine web of intrigue for a few days has made me think twice about this tech ecosystem of ours and what sorts of behaviors we are enabling with it. How many VCs and powerful people hate what Superhuman is doing with people’s privacy but won’t say anything because they aren’t sure if another company in their portfolio does something similarly sketchy with data? How many won’t say anything because they are concerned about their relationship with Andreessen Horowitz?

This episode has also made me take stock of whether there’s anything in my own life which is collecting data it doesn’t need to collect. Someone on Twitter brought up the fact that I use Mailchimp to send out newsletters. That’s a good place to start. A few years ago, I enlisted Mailchimp to automate newsletter creation for me. I wanted to give people an easy way receive an email every time I wrote a new post. That’s about two or three times a year. Mailchimp makes this so easy that since installing it, I’ve never once logged into the service. I didn’t even know what, if any, data they were collecting aside from the number of subscribers I had. Turns out, they can collect a lot more data than I am comfortable with. Thankfully you can disable substantially all of it, which I have done. It bothers me that these services are choosing to collect all of this data for people who don’t even need it or want it. It turns people into “unwitting data collectors”.

It reminds me of the early days of Android when developers immediately asked for every single permission they could get from you. Now the conventional wisdom is to only ask for what you need, when you need it. It makes things slightly better that people are at least opting into these newsletters, but to use my same test from the original post, there is no way they know how much data is being collected on them. That said, I’m generally not moved by straw man arguments that attempt to paint bulk newsletter analytics with the same brush as email surveillance. News organizations are well within their rights to employ the former while criticizing the latter.

The second thing someone asked me on Twitter is whether the company I work for uses tracking pixels anywhere. I’m not in sales or I.T. so I have to look into how different people use analytics over here, but I imagine there are a variety of ways. I’m going to be proposing an explicit policy against the sort of thing described in this article this week and I don’t expect that will be controversial.

Ok, so back to Superhuman.

We are left now in a better state than we were last week. The threat level has decreased. But I am still left wondering, why is Superhuman taking this feature — which clearly creeps people out — and doing barely more than the minimum to make it less creepy? Rahul said exactly why in his post:

“If one of us creates something new, and that innovation becomes popular, then market dynamics will pull us all in that direction. This is how we ended up with location tracking inside of Superhuman, Mixmax, Yesware, Streak, and many others.”

Rahul is not wrong. But that is not how the greatest innovators think. The reason Slack is now an $18b company whose software is loved by millions of customers is that Stewart Butterfield created a new workplace communications tool based on how he thinks workplace communications should work. Stewart and team looked at what tools people were currently using, invented a new service full of things that seemed good, and left out everything that seemed bad. Are there any deceptive, creepy, or harmful features that exist in Slack because they already exist in other products? Not that I can think of. Someone please tell me if I’m wrong. Heck, Slack doesn’t even have read receipts! And it would be easy to design them ethically within Slack if they wanted to.

Either Rahul thinks email apps should be able to spy on recipients’ behavior without their knowledge or permission, or he doesn’t think they should — but he’s doing it anyway because other bad actors do. Neither of these represents the standard we should hold our entrepreneurs to… especially those we point to as models for great design and great leadership.

The other thing that’s been bugging me is that Superhuman’s other co-founder, Vivek Sodera, has openly compared Superhuman to Apple. See this thread:

Notwithstanding the fact that I believe Google could extinguish Superhuman’s entire existence with the flip of an API access switch, it strains credulity to see how the decision to surreptitiously collect behavioral data on unsuspecting users is Apple-like at all. Vivek is talking here about whether they will license their data out in the future, but still… if you are going to say you are like Apple, then you should at least try and act like Apple. Do I think Apple would ever insert invisible tracking pixels into emails so senders could monitor the actions of recipients without their knowledge or permission? Not in a million years. Do you?

To test my assumptions about how Apple, and in particular Steve Jobs, might approach a problem like this, I asked the only person I know who has worked directly for Jobs, across several decades: Mike Slade. Mike is the founder of ESPN.com, the original product manager of Excel, and worked directly alongside Jobs at both NeXT and Apple. Here’s what Mike said to me:

“Steve was the most consumer-first person I’ve ever worked with. If he didn’t like what the consumer was going to experience, he changed it. This functionality would’ve definitely creeped him out and he would’ve never implemented something as creepy as this.” — Mike Slade

Sadly, we’ll never know for sure, but this makes sense. Jobs used to talk a lot about the importance of taste in product development. That is exactly the concept that is missing here.

You just raised $36m so you could build a product for the long term. You think tracking pixels in emails are even going to be around in a few years? Differentiate yourselves from your competitors by giving a shit about privacy. Think Different.

To show you how this might work, I’ve taken the liberty of redesigning your sales pitch for you. Here is how you currently describe Read Receipts on your front page:

Now here’s how it would look if you decided to take a stand on privacy and protect people from both tracking and being tracked:

I feel like I am doing an unusual amount of free work here. THIS is the sort of morality I want to see in enterprise software. It’s funny, one of the things people like to talk about is how the iPhone kicked off “the consumerization of enterprise software”. Meaning, because the iPhone set the bar so high for how consumers experience digital products, all enterprise software eventually rose to meet this bar. If we can now expect our enterprise apps to look and feel as nice as our consumer apps, why can’t we also expect them to behave as nice?

To harken back again to the tao of Steve: “Design is how it works.”

Alright, that’s all I have on the subject of Superhuman specifically. Take my advice or leave it. It’s your company.

A couple of more things before I go. One of the valid criticisms of my article from last week is that I didn’t call out any of the various other companies that enable email spying. This is fair. I frankly didn’t know about most of them, since I don’t use email tracking myself. For instance, I had heard of Mixmax but thought it was just an extension which let people book time on your calendar (it does this too). I am more than happy to name the names of every company who does this. From Rahul’s post, that looks like Mixmax, Yesware, Streak, Mailtrack, and HubSpot (whose founder is a Superhuman investor). There are probably others too. To all of you: what you are enabling is bad and you should feel bad about enabling it. None of you pitch yourself as a well-designed email client so you avoided attention in my first post, but isn’t there a way for you to operate your business without enabling your customers to spy on their customers? Mixmax, you have that useful calendar thing. Is that not enough? HubSpot, Streak, and Yesware, you offer a bunch of services that are unrelated to this. Mailtrack, welp… this seems like pretty much all you do from what I can tell.

Is this stuff even useful in a material way? If you send someone an email and they don’t respond, you can either let it go or reach out again. Does knowing whether someone read it really change what you’re going to do? On top of that, aren’t we already in a world where you’re getting false positives and false negatives from that data? If I have images off (which, for the love of god, everyone should at this point), you’re seeing that I haven’t read email, when maybe I have. If Gmail or something else is proxying my email images, you might be seeing that I have read email, when maybe I haven’t. The data may be “usually right” because most normals don’t pay attention to this stuff, but how can you be sure? You can’t. This seems like a case of very low value data being collected and distributed in a potentially very harmful way.

To wrap things up, I want to address the final issue brought up from the first article: what are the big three mail platforms (Apple, Microsoft, and Google) doing to protect us? The answer seems to be “some, but not enough”. All three allow users to disable images, but none make that a default. I could make the argument that email should be text-only by default, but I don’t think that’s realistic given the sorts of emails people subscribe to these days (real estate listings, deals of the day, etc). Accepting this, it seems like email providers should use the same sort of filtering they use to keep us safe from malware. If an email with a Mailtrack pixel comes in, for instance, strip it. You’d have to maintain a growing list of these things as they mutate across IP addresses, but it would send a strong signal to the industry that this sort of stuff is on the outs.

Google and possibly also Microsoft could also stop this stuff from the other side: disallow extensions which provide this functionality. You don’t have to kill most of these companies’ entire businesses. Just specifically disallow this behavior.

Because neither of these solutions stops companies from using large, visible, legit images in their emails to provide the same tracking abilities, the big three should also proxy and cache remote images in email whenever they can. I believe Google already does some sort of this, but it’s unclear to me exactly how obfuscatory it is. I don’t believe either Microsoft or Apple does any of this yet.

This is almost certainly a case of “if you think the solution is easy, you don’t understand the problem”, so I recognize there’s a lot of implementation complexity I’m missing here. I guess I would just like to see all of these companies do everything they can to protect the majority of the world, who — unless they were paying attention last week — still doesn’t know they are naked with their curtains open for all people using spyware pixels to see.

Perhaps if the big platforms aren’t able to sufficiently protect people, the last resort is the law. I’m not a COPPA or GDPR expert, but it seems crazy that collecting information via a website about someone under 13 without parental consent is illegal, but providing software that can automatically track that child’s movements when they open an email is not.

This whole thing may already be advancing through the legal system, as just a few days ago, the British Information Commissioner’s Office issued guidelines requiring consent and transparency for email tracking pixels. If ethics can’t keep companies from doing these sorts of things, maybe fines can.

It seems to me we’ve still got a lot of work to do here to keep people safe. Until that work is done, the best way to stay safe is to follow the same two pieces of advice from my previous article:

1. Don’t use Superhuman yourself. They have not given a date for when they will protect you from other people’s tracking pixels and they have not shown a proper appreciation for privacy. Remember, when Superhuman says “you can turn it off”, that only means you can stop sending your own tracking pixels out.
2. Turn off remote image loading in whatever email client you use. You may also want to consider using an always-on VPN to keep your location from ever being revealed.

Thank you for reading this. Stay safe out there.

It is disappointing then that one of the most hyped new email clients, Superhuman, has decided to embed hidden tracking pixels inside of the emails its customers send out. Superhuman calls this feature “Read Receipts” and turns it on by default for its customers, without the consent of its recipients. You’ve heard the term “Read Receipts” before, so you have most likely been conditioned to believe it’s a simple “Read/Unread” status that people can opt out of. With Superhuman, it is not. If I send you an email using Superhuman (no matter what email client you use), and you open it 9 times, this is what I see:

That’s right. A running log of every single time you have opened my email, including your location when you opened it. Before we continue, ask yourself if you expect this information to be collected on you and relayed back to your parent, your child, your spouse, your co-worker, a salesperson, an ex, a random stranger, or a stalker every time you read an email. Although some one-to-many email blasting software has used similar technologies to track open rates, the answer is no; most people don’t expect this. People reasonably expect that when — and especially where — they read their email is their own business.

When I initially tweeted about this last week, the tweet was faved by a wide variety of people, including current and former employees and CEOs of companies ranging from Facebook, to Apple, to Twitter:

It was also met critically by several Superhuman users, as well as some Superhuman investors (who never disclosed that they were investors, even in past, private conversations with me). I want to talk about this issue because I think it’s instructive to how we build products and companies with a sense of ethics and responsibility. I think what Superhuman is doing here demonstrates a lack of regard for both.

First, a few caveats:

1. I was invited into the Superhuman service several months ago. I began their onboarding process, was excited to try using it as my primary email client, and bailed out the moment I found out about this spyware functionality.
2. Nothing in this post evaluates other things about the Superhuman service. I’m not here to tell you it isn’t fast, isn’t good looking, or doesn’t save you time. I suspect it is all of those things, in fact. So if your response to this post is “BUT I LIKE IT!”, I believe you that there are things to like about it. That is not the subject of this post.
3. I know people whom I consider to be ethical people who use workplace software that embeds tracking pixels in emails.

Second, I want to talk about why this particular issue is so important. Not why privacy is important; we are all already learning that the hard way. Rather, why making ethical decisions at the earliest stages of your company is important.

When a company first forms, there are no norms or principles guiding how its people should make decisions. It’s basically just what’s in the founders’ heads. With each decision a company makes, its “decision genome” is established and subsequently hardened. You’ve decided in your first month that you’re only going to hire engineers from Top 10 engineering schools? That’s now part of your genome and will determine the composition of your company. You’ve decided to forgo extra profits by keeping your prices low for consumers? That’s now part of your genome. You’ve decided to employ a single dark pattern to trick users into adding more things to their shopping cart? Part of your genome.

The reason this matters is that what may seem like small decisions early on become the basis for many more decisions down the road. These decisions affect your ethical trajectory as a company. Let’s use the dark pattern example. Maybe the shopping cart thing was pretty minor and you were able to rationalize it internally in a variety of ways, including the fact that the extra item in the user’s cart was inexpensive and provided value (like a product warranty, for instance). Down the road, when employees want to employ more dark patterns, here is how the conversation would go:

Greg: “Hey, we aren’t getting enough people to opt-into our mailing list when they sign up. Can we try maybe unchecking that box by default but using language such that leaving it unchecked opts people in?”

Desi: “Wouldn’t we be intentionally deceiving users if we did that?”

Greg: “Uhhhh, we already add things to your shopping cart that you don’t even ask for!”

Desi: “True. This seems like less of a big deal than that. I guess I’m OK with it.”

If you’ve never worked at a tech company before, this is how things go. When faced with making a product decision that is even mildly uncomfortable, employees often first look towards expressed company principles like “Always put the customer first”, but the next thing they look for is precedent. What other decisions have we made that look like this one? Designers do this. Engineers do this. Product managers do this. Executives do this. It’s an easy way to inform your current decision, and it’s also an easy way to cover your ass. Imagine the above decision was made by a product manager, and later on the company was called out publicly on it. The CEO or Head of Product marches over to the product manager and says “what were you thinking here?!?” The product manager needs only to point to the shopping cart behavior in order to let him or herself off the hook.

The point here is that companies decide early on what sort of companies they will end up being. The company they may want to be is often written in things like “core values” that are displayed in lunch rooms and employee handbooks, but the company they will be is a product of the actual decisions they make — especially the tough decisions.

So back to Superhuman. Here we have a company that professes to create a better email experience mainly through better design and engineering. So far so good! Those who know me know that I would be among the first people to sign up for something like this and also among the most vocal to evangelize it. Heck, I love a certain showerhead so much that I:

1. Have bought one for every shower in every place I’ve lived for the past several years.
2. Bought one for every member of my leadership team at Twitter for Christmas.
3. Used to keep a brand new spare one in my trunk to give away to friends every time the subject came up.
4. Turned the damn showerhead emoji on Twitter into a Flipside. Actually, my team did this, but as an homage to my love for it.

In other words, when I see great design, I proactively try to spread it as far and wide as possible.

What I see in Superhuman though is a company that has mistaken taking advantage of people for good design. They’ve identified a feature that provides value to some of their customers (i.e. seeing if someone has opened your email yet) and they’ve trampled the privacy of every single person they send email to in order to achieve that. Superhuman never asks the person on the other end if they are OK with sending a read receipt (complete with timestamp and geolocation). Superhuman never offers a way to opt out. Just as troublingly, Superhuman teaches its user to surveil by default. I imagine many users sign up for this, see the feature, and say to themselves “Cool! Read receipts! I guess that’s one of the things my $30 a month buys me.”

When products are introduced into the market with behaviors like this, customers are trained to think they are not just legal but also ethical. They don’t always take the next step and ask themselves “wait, should I be doing this?” It’s kind of like if you walked by someone’s window at night and saw them naked. You could do one of two things: a) look away and get out of there, realizing you saw something that person wouldn’t want you to see, or b) keep staring, because if they really didn’t want anyone to see them, they should have closed their blinds. It’s two ways of looking at the world, and Superhuman is not just allowing for option B but actively causing it to happen. It’s almost as if Superhuman is aiming a motion-sensitive camera outside people’s windows and sending alerts when there is motion. It’s automated and designed to capture info when your family, your friend, your co-worker, or your victim is not aware. You may think “victim” is too harsh of a word to use here, but remember, we aren’t talking about you. We are talking about anyone who might use Superhuman.

Even though most of the feedback I’ve gotten about raising this issue has been supportive, here is a collection of replies I’ve gotten on Twitter, so we can address them all in one place:

1. “Email clients have done this for years. Even Apple does this with iMessage.” — Multiple People. This argument is naive at best and disingenuous at worst. Superhuman’s competitors are Apple Mail, Gmail, and Outlook. Exactly zero of those companies insert a tracking pixel into their emails. Furthermore, both Outlook and iMessage use Read Receipts that are turned off by default and controlled completely by the receiving user. In other words, when you buy a new iPhone or start using Outlook, no one requesting an Outlook or iMessage read receipt can receive one without your explicit permission. Furthermore, even if you do turn those on, it’s a simple one-time receipt… not a log of times and geolocations every time the recipient views the message. Both Microsoft and Apple — as well as other messaging platforms like Twitter, LinkedIn, and Signal — have designed their read receipts in an ethical way. Superhuman has not. Also ask yourself what the backlash would be if a company somehow retrofit these spying capabilities on top of iMessage. What if every single time you viewed someone’s text message, your phone sent a timestamp and location to back to the sender, creating a map of your movements? There’s a reason Apple doesn’t allow this.
2. “Other tools like MailChimp, PersistIQ, SendGrid, and MailTrack do this.” — Multiple People. Superhuman is an e-mail client, much like Gmail, Outlook, and Apple Mail. It is not mail automation software. Mass mailing companies, for the most part, use that technology to track open rates and also to *stop* sending out emails to people who haven’t opened them in months. There are indeed some sales-enablement companies that use this technology to track individual opens, and I find that just as creepy. The main point here is: just because technology is being used unethically by others does not mean you should use it unethically yourself. Harmful pesticides have also been around for years. That doesn’t mean you should use them yourself.

3. 

   Where to start with this one from Gary Sheynkman. You, the sender, do not get to decide how I, the receiver, respond to you. Not returning your email right away is not passive-aggressive. It’s often just being busy or prioritizing. As pointed out by Erica, being “left on read” can send unintended hurtful messages. Furthermore, in the workplace, this can be used as a tool to monitor or coerce around-the-clock work.

4. 

   This is from Nick Abouzeid, a Superhuman investor (who did not disclose that, but I got it by going to his website) from the aptly named “Shrug Capital”. This comment gets to the crux of the ethics question we are talking about here. When you are making software, you can either say “lets exploit everything in the world that can act to our benefit” or you can say “lets build something that’s great for the world”. This person looks at all people who use email as potential people to exploit. How many people use email? 2 billion or so? How many of those have images turned off? Probably a tiny percentage. And how many are expecting that every time they open an email from a friend, their friend gets notified with their geolocation? I would guess almost zero. So what this person is essentially saying is that since most people leave their curtains open at night, it’s ethical for the company he funds to film what goes on inside. Furthermore, Superhuman doesn’t even let its own customers turn images off. So merely by using Superhuman, you are vulnerable to the exact same spying that Superhuman enables you to do to others. He is right about one thing though: because of spyware-foisting companies like Superhuman, you should unfortunately turn off all image loading in your email client.

When you start to think about all of the ways Superhuman can be used to violate privacy, you really wonder why The New York Times spent 1,200 words on a tongue-bath that doesn’t even talk meaningfully about privacy issues at all. We don’t need journalism to tell us where venture capitalists are putting other people’s money. We need it to examine the ramifications of the technology we are pushing into the world and in what ways it might shift the Overton Window for Ethics in either helpful or hurtful ways.

There are some bad people out there, so what are some bad things that people can do with technology like this? Here are just a few:

• An ex-boyfriend is a Superhuman user who pens a desperate email. Subject: “I’ve been thinking about us”. He sends it to his former partner. She reads it when she gets to work in Downtown Los Angeles at 9am. She reads it again before dinner with friends in Pasadena at 7pm. She reads it again at home in Santa Monica at 1am. Over the weekend, she takes a trip to New York and reads it again. Twice. She decides not to answer the email, because her ex has stalked her in the past and she doesn’t want to communicate any further. But because of the tracking pixel, her email is always communicating, and it’s sharing info she does not want to send and doesn’t even know she is sending. She didn’t reply, but her ex still knows she read his email five times, including most likely in her bed. And he knows she took a trip to New York.
• A pedophile uses Superhuman to send your child an email. Subject: “Ten Tips to Get Great at Minecraft”. Your child keeps the email in their inbox and refers back to it often over the course of a year. Sometimes when they are at home in Vermont. Sometimes when they are at school in New Hampshire. Sometimes when they are with their grandparents in Massachusetts. Every time your child opens the email, that person knows generally where they are (or specifically, if they have other info to triangulate against).
• Superhuman decides they can make more money by supplementing their subscription fees with data licensing agreements. Maybe they decide to leave out data from paying Superhuman customers but they include location history from every single person you’ve ever emailed, because they have no contract with those people. Location maps with timestamps, other insights about things like working hours and locations, device types, and whatever else they collect. That data is then used to target those people in a variety of ways. If Superhuman is truly willing to commit to never license any data to anyone for any reason, they should be able to clearly say so right now. But they probably won’t, because they want to keep their options open.

I understand wanting to cover a new product, but an outfit as respected as the Times needs to go deeper on this stuff. Heck, I’m already at 4000 words — on a single subject — and I just wrote this on a whim over the weekend.

Even though I wish companies didn’t make the sorts of product decisions Superhuman has made, I’m glad they are at least showing their cards early (and appear to stand by them) so I can avoid their service. Not just on principle but because I have no reason to trust them with any of my data. Remember that they require full access to your Gmail in order to do their thing. Fast forward a year or two and I can see them licensing location data either from their own customers or their non-customers to a third-party for any number of distasteful purposes. They say they have a privacy policy that forbids this, but I don’t read their policy that way at all. It allows and even specifies all sorts of things they can do. Here’s an excerpt (emphasis mine):

HOW WE USE TRACKING TECHNOLOGY TO COLLECT INFORMATION

We automatically collect usage information when you visit our Website or use the Service through the use of tracking technologies, including tracking pixels and similar technology (collectively, “Tracking Technologies”). We may use the data collected through Tracking Technologies to: (a) remember information so that you will not have to re-enter it the next time you visit the Website or use the Service; (b) provide and monitor the effectiveness of our Service; (c) provide functionality of the Service including read receipts; (d) monitor and collect analytics data using third-party tools like Google Analytics in order to help measure traffic and usage trends for the Service; (e) diagnose or fix technology problems; and (f) otherwise to plan for and enhance our Service.

The form of this paragraph is very familiar to lawyers. Specify some stuff that sounds mundane and then leave yourself all sorts of escape routes. Item F is essentially a universal license to do whatever they want (i.e. “We’ve ‘enhanced’ our service by using your location data in a new way!”). Now, I’m not saying this privacy policy is out of the ordinary at all. I’m just saying there is nothing about Superhuman’s Terms of Service that prevent them from making further decisions that violate your privacy in the future. Not to mention, companies can change their policy at any time. When you use a product, you need to trust the people who are building it — not the documents their attorneys create. And finally, once again, because of this spyware pixel, most of the people they are collecting information on aren’t even Superhuman customers and never even signed up for this policy.

So what would I do if I were Rahul Vohra, Superhuman’s CEO?

The first thing I’d do is apologize and remove this functionality for everyone. You don’t need to take out a front page ad in the Times. Just own the mistake and disable the feature unless and until you can design it in an ethical way. Don’t keep it up for a year while you work on it. Take it down. This would show responsibility and regard for doing the right thing. A sign of an honorable company is when it is willing to learn, take responsibility, and improve.

Next I would recalibrate how important it is to even offer Read Receipts. Superhuman seems to be doing just fine in terms of customer satisfaction. I know some people like this functionality but does the success of Superhuman’s business depend on it? I would guess not.

Third, if Superhuman really cared about protecting the privacy of its users, they would actually provide the exact opposite of this feature. Protect all Superhuman users from emails loaded with surveillance pixels, do it by default, and never embed them in their own outbound emails. There are a few browser extensions that do this decently while keeping most benign images turned on, but this would be a great feature to have baked into an email client. Use this moment as a turning point to honor all of the other work going on at the company and turn this negative into a positive.

Finally, if I still didn’t agree that tracking the geolocations and reading behavior of unwitting people was deceptive, I’d wear it on my sleeve:

A good ethics test for investors, employees & users of Superhuman. If you use SH’s default spyware behavior, you should be willing to change your signature to this:

– Sent via Superhuman. Every time you open this email, the time and your location are sent to me.

Who’s first?

— Mike Davidson (@mikeindustries) June 27, 2019

A lot of Superhuman’s customers — and I assume most of its employees and execs — use the “Sent with Superhuman” signature already. If you are so sure that automatically receiving a recipient’s geolocation every time they read one of your emails is OK, you should be OK with telling them that when you send them an email. In fact, since it’s a feature you are proud of, you should be more than happy to market it so clearly, right? (In case you’re wondering, exactly zero people stepped up to do this. Not Rahul Vohra, no employees, no investors, and no customers.)

Before I close, I want to talk about blame.

I don’t automatically blame Superhuman designers for this, because I don’t know if they fought for it or against it. Likewise, I don’t blame Superhuman engineers, product managers, or anyone else, for the same reason. For all I know, this was something the team pushed back strenuously on and lost. If so, thanks for fighting the good fight, and you should have your equity grant doubled for trying to do the right thing. If not, this whole article also applies to you. The only person I know for sure shares some or all of the responsibility for this is Superhuman’s CEO, Rahul Vohra. He is the only employee I’ve seen actively defend it (although perhaps others have), and it’s safe to say he was intimately involved in its development.

This is also important: I do not know Rahul. I don’t know if he’s nice, mean, a good person, a bad person, likes his steak medium rare or well-done with ketchup, or anything else about him. I make no value judgements about him as a human, and as with most other humans, I try to assume the best about him. This article is about a very specific decision of his that I find to be dangerous and wrong. Whenever I see something like this, I always give the benefit of the doubt and assume the person simply doesn’t realize the downside consequences of their decision. I brought this up several months ago and the company did nothing to address it. I brought it up again last week and still nothing. In light of that, and in light of some of the responses from investors defending Superhuman’s surveillance behavior, I felt justified writing a proper piece about it.

Finally, if you are a user wanting to protect yourself against automatically having your email behavior and geolocation sent to people who use Superhuman and other surveillance tools, you need to do both of these things:

1. Don’t use Superhuman yourself. As mentioned earlier, Superhuman leaves you unprotected from spying because they don’t allow you to block these spyware pixels. It also turns you into an unwitting information collection machine, aggregating info on every single person you send email to. Possibly including your parents, children, partners, and friends.
2. Turn off remote image loading in whatever email client you use. Almost every client these days allows you to do this, with the strange exception of Gmail for iOS. If you are a Gmail user, I recommend switching to something like Outlook on your iPhone. It’s free and allows you to use your existing Gmail account. No migration necessary. Apple Mail is fine too.

So to sum up — whether you are an email provider or an email user — don’t surveil, and don’t allow yourself to be surveilled. I hope Superhuman does the right thing and decides to help stop this problem instead of trying to normalize it.

Some people survive on talent, vision, persistence, or a host of other superpowers, but to make up for what I lack, I’ve always been a tool nerd.

Whether it was messing around with Print Shop on a Commodore 64 when I was 10, teaching myself Photoshop 3.0 in my teens, or learning HTML via “HoT MetaL” while most designers were only doing print work, aggressively learning the tools of the near future has been one of the only consistencies of my career.

For that, and other reasons I’ll explain below, I’m incredibly excited to announce that after a refreshing two-year sabbatical from work, I’m joining one of my favorite companies — InVision — to head up Partnerships & Community!

We are entering a golden age of product design tools right now, and I’ve seen first-hand what introducing great prototyping and collaboration software like InVision can do within a company. It breaks down barriers between different groups and gets everyone thinking about user experience. It demystifies what product design actually is. It replaces 50-slide presentations and exhaustive spec documents with quick-to-create working demos that everyone can hold in their hand. More showing, less telling.

As my friend at Google, Darren Delaye once told me, there’s no better way to communicate a product idea than pulling out your phone and saying “Hey, wanna see something cool?”

When Clark and I first started talking about working together a little while ago — and about this role in particular — I’ll admit I had some question marks. In particular:

1. InVision is a fully distributed company with no offices.

A lot of people probably view this as a positive, but the thing I miss most about my last job at Twitter is being around my team and all of the other great people there. I’m an extrovert, and even if I have to brave open-office plans and commute times, being around teammates has always been important to me. Video calls, in fact, have always felt like a burden because face-to-face is the default mode of communication at most companies.

I had a really tough time evaluating what working remotely would be like, but in talking to Clark, Stephen, Aarron, David, Hilary and others at the company, everyone says exactly the same thing: it sounds like it’s going to be awkward, but after a couple of months, you never want to work any other way again. It’s great to be able to spend the first few hours of your day working from your couch, then go on a run whenever the weather clears up, and then spend the rest of the day working from your patio or your local coffee shop… all without ever getting stuck in traffic! InVision even gives you a $100 coffee & tea credit every month to encourage you to explore new surroundings.

It seems that when everyone is remote, the working dynamic changes. You aren’t sitting in a room with 10 people and then figuring out a way to dial in your poor London teammate with a choppy internet connection. You aren’t keying off of all of the social cues in the conference room and losing nuance from your one teammate in India. When everyone’s in the same boat — even if it’s a metaphorical boat held together by thousands of miles of fiber — something apparently changes.

I am now looking forward to this social experiment in telepresence, even if it means I have to remove the Zuck Tape covering my laptop’s camera. I think InVision is correct that this will be the new normal for a lot of companies over the next decade, and if you are a designer who doesn’t want to (or can’t) live in San Francisco, this seems like good news for you too. Either way, I will report back in a few weeks to let you know how it’s going.

2. I’m used to working on consumer products, as opposed to products that help people make other products.

Whether at ESPN, Newsvine, NBC, or Twitter, most of my career has been spent building things that consumers use. In evaluating each of those opportunities, I’ve tried to ask myself “what kind of impact is this going to have on the world?” This opportunity is a bit different because InVision doesn’t really touch consumers directly, but rather, it touches the designers, engineers, PMs, researchers, writers and others responsible for making the products that touch consumers. In that sense, it’s hard to trace the social impact of your work because you aren’t even aware of all the products that are being built with it. Having used InVision regularly myself, however, I am confident of three things: it tends to raise the profile of design work inside of companies, it facilitates a more inclusive product development process, and it ultimately helps create better user experiences. All great things.

You may say to yourself “but I like another tool better!” That’s totally fine. Any of the options available today are light years better than what we did ten years ago when we emailed JPEGs back and forth. I happen to think InVision is the best set of tools out there for entire organizations to use (with more products and capabilities on the way), but a world in which designers have several great options to choose from is a world I want to live in. Competition breeds excellence, and there is a lot more work for all of us to do.

One last note on tools and their impact: even though it was over ten years ago now and it started as a fun little hack, sIFR is still one of the projects I’ve enjoyed working on the most. None of us ever made a penny on it, or even tried to, but watching that little tool help people beautify typography across the web was really fulfilling. Seeing the need for it slowly disappear with the advent of TypeKit and proper web fonts was just as satisfying. It’s great to work on things that inch the world forward and make other people’s work better, and I look forward to doing that again in whatever ways I can at InVision.

3. The output of my work will, for the most part, not be directly within the product.

The role I’m taking on at InVision is not within Product, Engineering, or Design, so I won’t actually be working on the products themselves (but you can be sure I’ll be in people’s grills with ideas and feedback! ).

Instead, I’ll be doing the following:

• Working with hundreds of companies and design teams around the world listening to how they currently develop products, how they want to develop products, and how we might be able to help.
• Keeping an eye on interesting new products and teams in the design software space and working on acquisitions when it makes sense.
• Designing and executing product integrations that bring the functionality of InVision to other platforms, and vice versa. InVision is already integrated with the largest platforms that drive digital product success, including those from Slack, Atlassian, Dropbox, and Microsoft, but there are still a lot more nodes in the digital product ecosystem to connect. The goal is to make the workflow of product design as seamless as possible, no matter what assortment of platforms a team is using.
• Emceeing InVision’s Design Leadership Forum, which hosts private events for design leaders from around the world. Its goal is to advance the practice of design leadership by creating a community where leaders can learn from one another.
• Further building out InVision’s programs within the traditional and continuing education spaces.
• Working on inclusive ways to bring the design community together, both online and off.

It’s a different sort of role for me, but at the same time, I’ve actually been doing a decent amount of exactly this sort of thing during my time off.

In some ways, this seems like the perfect opportunity at the perfect company right now, and yet, in other ways, I’ve never done anything like it! One thing that feels palpable already, however, is that this is a company driven by producing great experiences — for its customers, its partners, and its employees — and for that reason, I already feel at home (also, I *am* at home).

I’m not sure what my hiring plan is just yet, but if I’ve ever worked with you in the past or if you see anything you like in the 71 positions posted here, feel free to reach out to me directly! If you’re interested in helping power the next decade of digital product development from the comfort of wherever you choose to work, now is a great time to be joining InVision.

You may hear things like “Design is very important to us” or “Design has a seat at the table” or even “We’re a design-driven organization”. As a designer evaluating job opportunities, should you take statements like this at face value or might you be able to get a clearer picture by asking questions, reviewing a company’s products, and other investigative means?

Throughout my 20 years in design, I’ve worked in everything from design-hostile to design-driven environments, and I can tell you that succeeding (and being happy) within each requires a different mindset going in.

Before discussing strategies, let’s describe several types of organizations along the design spectrum so as to identify what they look like. Importantly, when I say things like “design-driven”, I don’t necessarily mean Design-ER driven. In other words, it doesn’t mean that designers call all the shots. It just means that great care goes into every detail of the user experience of a company’s products. That level of detail could come from engineers, researchers, execs, or any number of other people (and often does!), but it also tends to correlate with designers playing key roles at the company.

The Spectrum of Design Drivenness

Design Hostile

CRMster is a 20-person startup that develops Customer Relationship Management software. There are 10 salespeople, 8 engineers, 1 CEO, and one contract designer. Most product decisions are made by the CEO and one salesperson. The rest of the team just builds whatever they are told to build. If a designer or engineer brings up concerns about a product feature, they are told to just stick to the program and produce what the CEO asked for as quickly as possible.

Design Ignorant

GitBusy is a 5-person startup building a new way to sync files across computers. All five team members are back-end engineers and they have spent their first year building out core functionality. The product is a bear to use, but it’s starting to work reliably. They keep making minor usability improvements but they’ve never thought to hire someone full-time who specializes in user experience.

Design Agnostic

MegaloBank is a Fortune 100 financial institution that employs over 10,000 people. They employ plenty of designers and design-minded people around the company, but mainly as support for other teams. If you asked the CEO of the company what his or her designers did, the response would be something like “I think they make our logos and business cards.” Important product design work does get done at Design Agnostic companies, but the people who do it just aren’t looked at as core talent the same way as sales, engineering, or marketing might be. Their compensation unfortunately reflects this.

Design Interested

CellYou is a 20-year old wireless carrier, employing over 10,000 people. They are feeling the heat from their competitors and have just embarked on a high-profile effort to redesign their product line so it is much easier to use. They don’t have all the right people in place yet, they aren’t walking the walk in terms of a user-centered product development process, and they still pay their designers a lot less than PMs and engineers, but they are starting to talk about things in the right way and starting to recognize the value of design. It may take a few years, but they are moving in the right direction. A lot of companies who say they are Design Driven are actually in this category instead.

Design Driven

HyperBowl is a 500 person company that makes a versatile kitchen appliance which can cook hundreds of different foods. It started as one chef and one engineer, but even from the very beginning, there was a relentless focus on building product prototypes and iterating them rigorously based on how they performed with users. New products are developed only when they can perform important jobs for users. At HyperBowl, there are 10 full-time designers but everyone in the company considers user experience to be one of their most important job functions. Many decisions are made with data and research, but there’s room for subjectivity, taste, and long-term vision as well.

Those are the five archetypes you’ll generally run across in the market today.

The Challenges of Each

As a designer, you may immediately think to yourself “I only want to work for a Design Driven organization!” If your goal is to join an environment that immediately affords you the ability to practice great design, then this is a natural choice. Take Apple, for instance. Whether you are fresh out of school or a 20-year design veteran, as a new employee at Apple, you won’t need to spend any of your time convincing anyone of the value of design. You will be paid roughly on par with engineers, expected to help lead the product development process, and likely do some of the best work of your career. I have a bunch of friends who have worked at Apple, and one of them summed it up best: it’s like career rocket fuel. You may find the work/life balance unsustainable in the long term, but your time there will be unencumbered by any fights about the value of design.

A lot of companies (even some of the largest and most successful in the world) will tell you they are Design Driven, but they are actually one level away, in the Design Interested category. You should always maintain a healthy suspicion about this, in fact. Like our cellular carrier above, they are in the midst of a positive transformation, but they just aren’t there yet. What this means for you as a designer (or researcher, or front-end engineer) is that not that you won’t be respected to listened to, but rather that part of your job will be to move the company from its old way of doing things to a new way of doing things. This involves a lot more than just your technical skills. It involves the patience to work in suboptimal conditions and the willingness to help lead the process of becoming more Design Driven. Thankfully since the company is already Design Interested, the “what”, “when”, and “why” have already been taken care of for you, but the “who” and “how” are still open questions. You are part of the who that will help determine the how!

A large number of companies in the world fit into the next category: Design Agnostic. These companies have found a way to turn a profit without paying as much attention to user experience as they could or should. Sometimes when you find a market need that is strong enough, you can get away with selling a “merely adequate” solution. Other times, your business is specifically aimed at gathering the most profit for the least amount of work possible. Joining a company like this requires you to be cool with one of two things. Either you are content to produce “good enough” work in a system that doesn’t value you as core talent, or you are interested in taking on the much larger challenge of turning your company into more of a Design Driven organization. To be clear, thousands of designers have no problem with the former, and I have no problem with that career choice. In fact, sometimes it’s all that exists, depending on geography, experience, economy health and other factors. The latter, however, is one of the hardest and most substantial things you could ever accomplish in your career. Imagine being the person (or small group of people in this case) who got Google to care about design? If you find yourself thinking about joining one of the many Design Agnostic companies in the world today, don’t think of it necessarily as “settling”. Think of it as an opportunity to redesign the entire product development factory within. If you succeed, they’ll carry you around on a rickshaw.

The next category, Design Ignorant companies, are actually a bit easier to make an impact in than Design Agnostic companies. That is because Design Ignorant companies haven’t normalized the role of design yet. They simply haven’t experienced it yet. In fact, you may even be treated more as a hero upon your arrival at a Design Ignorant company than a Design Driven company. Going back to our example above with the file-syncing startup, imagine how much immediate impact you’ll make when you optimize the sign-up flow, improve the product copy, and flatten the navigation. If you do your job well, you’ll be appreciated right from the start. Unfortunately, you probably won’t be paid well, but Design Driven companies are usually the only companies that pay designers what they are worth at this point. This is changing for the better, but it is a multi-year process.

Finally, at the end of the spectrum, are Design Hostile companies. Think of the challenges and rewards here much the same as Design Agnostic companies except these companies have already decided that your craft is but a necessary evil for them. This by far the least desirable company type for people in our field to work at, but hey, there are plenty of cases of these sorts of companies turning around eventually. In fact, I would venture to say that using my definitions here, there are plenty of Design Agnostic companies today that ten years ago may have been Design Hostile. If you find yourself entertaining an offer from a company like this, you really need to determine how pliable they are with regard to how they view design and whether you’re ok with that.

Strategies to Know What You’re Getting Into

There are four ways to determine what sort of company you’re thinking about working at: looking, listening, asking, and verifying. You should do all four.

Looking

Thinking about working for that popular, growing auto insurance company in town? Start looking at their products. Does their visual identity seem professionally executed? How usable is their app or website? Go ahead and actually sign up if you can. Was the process reasonably well designed? Nothing is ever perfect, but often times, just spending an hour or two with a company’s product will give you a feel for how much they care about details. And when I say “details”, I don’t just mean how buttery smooth is the animation but also how smooth is the “Forgot Password” process?

Take notes as you go, in case you end up interviewing there. It’s always good to have firsthand knowledge and constructive criticism ready for when someone asks you what changes you’d make to their product (do this tactfully though, as you don’t know what factors went into a given product decision).

Make sure to also look at competitors’ offerings. While the auto insurance site may not be as modern as your favorite social networking site, maybe it’s head and shoulders better designed than all other auto insurance sites. In an industry that perhaps moves slowly in terms of technology upgrades, maybe this company is moving 10x faster than its competitors. That would be a pretty good sign.

Listening

When recruiters or employees of the auto insurance company try to pitch their company to you, they will usually do so in a way that portrays their company in as positive of a light as possible. In other words, although it does happen, you’ll rarely hear a prospective employer tell you “design is an absolute mess here”, even though it very well might be. Instead, listen for coded language. Things like:

“Over the last year, design has become a real priority.” Why? What happened before that?

“Design has a seat at the table now.” Cool, why now? What problems occurred before that?

“We’re looking to bring some fresh design blood into the company.” What are you doing with all of this blood? What problems with the current staff are you trying to solve?

Every statement should be examined for possible hidden meaning. By the way, these people are just doing their jobs. When I recruit designers, I also try to accentuate the positive. It’s your job as a candidate though, to dig deeper. Especially since your prospective employer will be digging deeply into your work as well.

Asking

In addition to responding to statements like the coded ones above, there are some good universal questions you can ask on your own:

“What is the attrition rate of designers at your company?” This should ideally be low.

“Are designers paid on par with engineers and PMs? If not, how close are they?” Pay should ideally be close or equal. Don’t be surprised if you get some bad answers or non-answers here, depending on company.

“Who does the Head of Design report to?” The CEO is always the best answer, but a great COO, CTO, CPO, GM is fine too.

“When someone needs to break a rule here, what is the process?” If they need help, perhaps give an example of a rule you’ve needed to break in the past, and ask how they’d handle it.

“What is the one negative or challenging thing about working here that no one is telling me right now and I will only find out after I start?” It’s a bad sign if they don’t have an answer.

“When someone has an idea for something they want to build, what is the process of getting approval and then building it?” Ask for a lot of detail here, right down to prototyping, user testing, and release.

“How do decisions get made when Design, Engineering, and PM can’t agree on something?” You’ll have to judge for yourself whether you like the answer.

“Tell me about a time when a product design was made subjectively or in the face of opposing data.” You might need to ask a particular person to get a good answer here, but if the answer is “never”, that’s indicative of an overly rigid decision making process.

“How are designers judged and promoted here? Is it different than Engineering and PM?” Ideally there is a thoughtful, well-articulated process in place that rewards behaviors and not just outcomes. If you’re judged solely on the metrics you move, that’s a bad sign.

It’s up to you to ask these questions with tact and at the appropriate times, but you are well within your rights to ask them. In fact, it’s a bit reckless not to.

Verifying

Do you know anyone who has worked for this company, past or present? If so, ask to get coffee with them. Depending on how secret your candidacy is, you may need to keep your questions general, but there is a lot to be gleaned from employees who aren’t trying to pitch you on anything. Start by asking what their overall experience was like. Would they recommend the company to a friend as a good place to work? Dig, if you can, into some of the things the recruiter or hiring manager told you.

“I’ve heard the decision making process is pretty egalitarian. Design, PM, and Eng all take part in that process.”

To which you might hear:

“Yep. It’s a great system. I always felt like an equal partner.”

Or:

“Haha. I am dying of laughter right now. If you’re in the room at all, it will just be to tell you what decision has been made without you.”

Importantly, when you hear things like this, you need to get a feel for whether those conditions still exist. Did this employee work there three months ago or three years ago? Is the person who enacted that decision-making process still even there? Because of the passage of time, you may get both false positive and false negative results from ex-employees. It’s ok though… it’s just a data point for you.

Also, at massive, sprawling companies, you may get different answers depending on which department’s employees you talk to. Maybe the auto insurance company’s consumer product is built in San Francisco and its broker product is built in Seattle. Maybe the working environment in San Francisco sucks but it’s great in Seattle.

So… by looking, listening, asking, and verifying, you can get a pretty accurate idea of what sort of company you are thinking about joining.

Fixing the Product Development Process, One Company at a Time

One of the reasons I wrote this piece was that I read a Tweet from a well-followed person in San Francisco talking about how the best companies in the world are all design-driven now. I get what he was trying to say, and I think that directionally, more companies are design-driven now than ever, but the vast majority of boots-on-the-ground designers in the world know how much work is still left to do. They also know that just because some high-profile companies have figured out that design is important, that doesn’t mean their own company in Seattle, or Omaha, or Bangalore has. A rising tide lifts all boats, but this is more of a slow motion wave you need to stay upright long enough to ride.

Finally, I also think it’s important to highlight the value of helping upgrade your own company’s product development processes. Designers love talking about the actual product design work they’ve done in the form of visual artifacts and launched services. Just as valuable, however, is the work that went into reshaping the processes that made these products possible. PMs make their own PM-centric contributions to what product development processes look like, and engineers do the same with their own lens. By adding your own perspective as a designer and improving the product development process at your own company, you’re accomplishing something you may not even get to accomplish at a place like Apple… and that, is something to be proud of.

(This post also available on Medium.)

After 11 years and 7 months in service, Newsvine, a participatory news site I launched with four friends on March 1st, 2006 was officially sunsetted by NBCNews.

Although I’ve been away from the company and the service for five years now, today brings back a rush of memories and some perspective on how the problems Newsvine set out to solve over a decade ago are actually the opposite of the problems that most need solving today.

In 2005, I found myself five years into a stint at Disney, wondering what was next for news. We owned ESPN, ABCNews, and several other media properties, but most of the fresh new takes on news seemed to be coming from non-traditional sources. Neither Twitter nor the iPhone had been invented yet, and Facebook was still just a campus dating site, but blogs were sprouting up by the thousands and sites like Digg and Slashdot were becoming popular destinations.

There seemed to be this growing bifurcation between mainstream media and citizen journalism. Mainstream newsrooms didn’t want to share their platform with amateur writers, and a lot of amateur writers grew more distrustful of mainstream media. Our big idea with Newsvine was to license the same Associated Press feed of professional reporting that made up the majority of what you’d see on a site like CNN.com, publish it faster than any other site in the world, and enlist citizens from around the world to create original, paid journalism around and alongside it… and open up every single piece of content for threaded discussion as well.

In other words:

CNN = AP Wire stories + Professional Journalism
Newsvine = AP Wire stories + Citizen Journalism + Discussion

… and we could do it all with a staff of under 10 people.

We didn’t know for sure if it was going to work, but the day we decided we’d be happy to have tried it even if it failed was the day we ended up quitting our jobs (incidentally, if you are thinking about leaving your job for a new risky thing, this is the acid test I recommend).

We spent about 6 months getting the company off the ground and the service into public beta, and it wasn’t long until extraordinary acts of journalism began appearing. Chris Thomas, one of our most prolific users, broke news of the Virginia Tech shootings on Newsvine before it appeared anywhere else. Jerry Firman, a 70 year old Newsviner from Ohio, got his name on the ballot for Congress and documented the process of running for office. Corey Spring, a student at Ohio State, scored an original interview with Dave Chappelle.

The design, tech, and operational work associated with growing Newsvine were fairly straightforward, but the one thing that seemed to get more and more difficult as the site grew was moderating and cultivating the community. Your first 1000 users are easy. People are just happy to be there. Then when you get to 10,000 you have a few fights here and there but nothing unmanageable. Even at 100,000, a small team of thoughtful people can stay on top of things. But when you hit 1 million, 10 million, and beyond, the community becomes much less intimate and more volatile.

Such was the case when we were acquired in 2007 by MSNBC.com (now NBCNews.com). Our site was already decently big but MSNBC’s was many times bigger… about 45 million people at the time. The post-acquisition work was twofold: 1) continue growing Newsvine as a standalone property, 2) use our technology to add registration, profiles, discussion threads, and other features to MSNBC.com. We also ended up powering all of the company’s blogs and some other things.

I ended up staying at MSNBC for about five years, and I would say the results of the experiment were mixed overall. On the upside, we provided technology that helped launch new editorial brands quickly and connect journalists to their audiences, but on the downside, “community” at that scale can be very messy. Additionally, with the eventual rise of Twitter and Facebook, Newsvine never grew to those usage levels. MSNBC.com was a great parent throughout though, and I have nothing but love for the people I worked with.

It’s interesting to compare Newsvine (and sites like it) to the now wildly successful fortunes of Facebook and Twitter. Newsvine at its core was a news site with a social network wrapped around it. Facebook at its core is a social network with news (and photos, and events, etc) wrapped around it. Twitter is probably structured more like Facebook in this regard as well, but its biggest challenge, in my opinion, has always been a lack of commitment to building those real-life social connections into the service.

When we look at how the average person’s news and media diet has changed over the last decade or so, we can trace it directly back to the way these and other modern organizations have begun feeding us our news. Up until 10 or 15 years ago, we essentially drank a protein shake full of news. A good amount of fruits and vegetables, some grains, some dairy, some tofu, and then a little bit of sugar, all blended together. Maybe it wasn’t the tastiest thing in the world but it kept us healthy and reasonably informed. Then, with cable news we created a fruit-only shake for half the population and a vegetable-only shake for the other half. Then with internet news, we deconstructed the shake entirely and let you pick your ingredients, often to your own detriment. And finally, with peer-reinforced, social news networks, we’ve given you the illusion of a balanced diet, but it’s often packed with sugar, carcinogens, and other harmful substances without you ever knowing. And it all tastes great!

As someone who has created Newsvine, worked at Twitter, and had many discussions with people at Facebook, I can tell you that this sort of effect was never “part of the business plan”. However, maximizing engagement was and still is, and that has led to a world in which what appears on people’s screens is what is most likely to keep one’s attention, as opposed to what is actually most important to know and understand.

The solutions to these problems will not come easy. They aren’t as simple as banning some jerk from Twitter or improving bot detection on Facebook. We’ve trained people to get their news and information from the cookie jar, and since we now know exactly what that world looks like, we must begin the job of untraining them… or at least engineering a healthy cookie.

We probably got a lot of things wrong at Newsvine, but one thing I still feel we got absolutely right is our longstanding tagline:

Get Smarter Here.

That’s really the only promise we ever wanted the service to fulfill.

After 800,000 articles, 65 million comments, 11+ years, thousands of new friendships, and at least one marriage and child from the site that I’m aware of, I’m confident it has fulfilled its mission for at least some who roamed its jungles.

(Special thanks to the entire Newsvine community. Without the dedicated efforts of all of you, we would have never had this special corner of the internet to write, meet new people, and have our perspectives changed. Thanks also to my partners Calvin, Mark, Lance, Josh, Tom, Tyler, Sally, Luke, Todd, Bobby, Dave, Arun, Jim, Mike, Brenda, Carl, Charlie, Rex, and everyone else at MSNBC.com for making this all possible. Also, extra special thanks to Nick, one of our investors, for introducing me to my wife, who I would have never met were it not for this little chance we took. And finally, thanks to my wife who helped get me through everything back then and since.)

(This post also available on Medium.)

Design, as a discipline, is very often brought into startups only when founders feel like they can no longer do without it. We are still at a point in our industry where those who have never worked with a great product designer before believe design is there to animate things, or make decks look shiny, or write blog posts about the geometry of a new logo.

The cascading effects of this sort of thinking are many. Products don’t end up evolving as quickly as they otherwise could. Design, as an industry, continues to struggle with uneven perceptions and expectations. And finally, designers themselves end up with very little equity in the companies they join because they didn’t join early enough.

There are a lot of ways that compensation in the tech world needs to change, but speaking from my own experience only, the clearest line between who makes life-changing money at a company and who does not comes down to when you started and at what level (the “when” part being more important usually). The difference between being a day zero founder and a day one employee is significant. The difference between being hired the day before a Series B round and the day after is significant. The difference between being hired the day before an IPO and the day after is significant. We are talking about, in many cases, one day or one week or one month being the difference between never having to work again when you’re done and barely even noticing a difference in your life.

Is getting in early just being “lucky?” Sure, to a point. But I would argue it’s hitching your horse to the right wagon that is the lucky part. Getting companies to value design and designers at the very earliest stages of product and company development is something we can change if we put some effort into it, and that is the part of Combine that I am most excited about.

If Adam and Soleio’s vision of assembling the best established and emerging designers in the world and helping place them inside of well-funded, early stage companies pans out, we will benefit from both better designed products and more designers who share financially in the success of what they help create. That is something I am happy to be a very small part of.

I am not a spokesperson for Combine, so any questions you might have should be directed towards Soleio or Adam. Actually, I can answer one question: it’s pronounced COM-bine. Anyway, if you are a designer or researcher interested in finding out more about the program, I encourage you to get involved. If this sort of thing was around ten years ago, I would have jumped in head first.

(This post also available on Medium.)

Every leader who has been around long enough has probably had a conversation like this after one of their team members resigns.

In an ideal world, people are open about every problem they face in the workplace, but great leaders know that we don’t live in an ideal world. There are a lot of reasons you won’t always know what might be brewing inside your team. People can be shy. People can be afraid of confrontation or retribution. People can blindly obey power structures because that’s how they’ve been taught. People can feel like “telling on someone” is disloyal.

A trip to the dentist’s office (!) yesterday reminded me how important the concept of proactively asking for the truth is.

When I left Twitter and moved back up to Seattle last year, I had to find a new dentist because the one I’d gone to since I was 15 had retired. I chose my neighborhood dentist, mainly out of convenience. Yesterday was my second visit, and let’s just say that for the second (and final) time the hygienist carved up my gums like she was auditioning for a Tarantino movie. I have pretty good dental habits with the possible exception of being on #TeamNoFloss, so there was no reason my gums should have gotten destroyed in the dental chair like they did yesterday. Halfway through the bloodbath, I asked her to ease up, and she did, somewhat, and then proceeded to tell me my gums were really bleeding a lot.

Thanks. I know. You did that.

Anyway, the moment I left the dentist’s office, I realized I had three choices:

1. Continue on like nothing happened.
2. Tell the dentist that her hygienist was a monster.
3. Say nothing and find a new dentist.

Those who know me well should have no trouble figuring out which option I chose.

I chose #3 for a few reasons. Firstly, I wasn’t about to get torn up again. Secondly, there are plenty of other dentists out there for me. And finally, I didn’t feel good about getting the hygienist in trouble.

But here’s the really important part that applies to management: if the dentist came up to me and actually asked me how the hygienist had done, I would have sang like a canary. Because she did not, I walked away non-confrontationally and this hygienist will now continue to drive people away from her clinic.

If you are managing people, chances are there are similarly troublesome things you should know that your team members will not feel comfortable volunteering without you specifically asking. I know this because I’ve experienced it simultaneously as a manager and an employee.

If my CEO sits me down for a 1:1 and says “how’s everything going?”, I am likely to rattle off a long line of accomplishments and things I think he or she would be excited about.

If instead he says “I’ve heard from others there are some challenges working with Jim Bob. Tell me what’s been difficult for you.” then that unlocks a level of candor that I may not have been comfortable volunteering on my own. In other words, I don’t think it’s my responsibility to proactively tell you every little negative thing across the entire organization, but if it’s important enough for you to ask me about it, I’m going to answer every question you have and give you as clear of a picture of the overall situation as I can.

There are three types of employees in the world when it comes to disclosing issues:

1. Those who will always tell you about problems.
2. Those who will never tell you about problems.
3. Those who will tell you about problems when asked in the right way.

I love my ones and am frustrated by my twos, but I feel like at least 9 out of 10 people are actually threes. One of the most important things you can do as a manager is assume everyone is a three and act accordingly. Here are some examples and how to get to the truth with each.

Situation:

You notice a team member withdrawing from discussions in meetings.

Wrong: In your next 1:1, ask them “how things are going”.

Right: In your next 1:1, tell them that you’ve noticed they’ve been especially quiet in meetings lately, and ask them why. If they don’t volunteer anything, suggest your own causes like “is it because no one lets each other finish sentences in there?” and let them correct you with real reasons.

Situation:

You hear about a situation in another department across the company where a woman was sexually harassed.

Wrong: Stay as far away from it as possible and assume if it was happening in your department, your employees would tell you.

Right: Pull some women (and men) on your team aside individually and ask them if this sort of thing is common inside the company and if they have ever experienced it. Ask them if it did happen to them, would they feel comfortable telling you about it? Assure them you want to know and that it’s everyone’s job to protect against abusive behavior, inside and outside the department.

Situation:

A new team member joins the company and you’ve heard nothing but positive about her during her first month.

Wrong: Assume everything is positive and stay out of the way.

Right: Have a 1:1 with her a month in and ask her “what are some of the things about this place that you find weird? What makes your job harder here than at the last place you worked at? What can I do to help you?”

Situation:

A team presents their project to you and wants your approval for launch.

Wrong: Assume everything went swimmingly and ask them if they need anything.

Right: Ask “of all the things you thought would go smoothly in this project, what thing went the least smoothly?” I love that question because it gets to so many different potential things to fix, from team communication, to dev tools, to security procedures, to legal requirements. (I stole this one from Dick Costolo, as it’s one of my favorite questions he likes to ask.)

When things go wrong on a team I manage, one of the first things I always ask myself is “what questions could I have asked to find this out earlier?” and then I start asking those questions more regularly. You will never get to a point where you are always asking the right questions at the right time, but half the battle is simply knowing that that is perhaps the most important part of your job.

There are many reasons why problems simmer below the surface for so long inside of workplaces, but as case after case has shown us, it’s only a matter of time before the ground truth catches up to you.

Luckily, the only tool you need to know what’s really going on at your company is your own inquisitiveness.

Ask and ye shall receive.

(This post also available on Medium.)

“When is this going to ship?”

“Real artists ship.”

The verb “ship” has a long history in the software development world and before that, the physical world. In the physical world, it originally meant “to transport something on a vessel”, and in the software world, it meant “to press a tape/disk/CD and send it out to consumers”. Since then, it has come to simply mean “release”, and even then, usually not in any sort of final form.

Everyone inside tech companies loves shipping. It’s the culmination of a lot of hard work and creativity from designers, engineers, PMs, researchers, and any number of other people, and when it’s good it puts a dent in the universe. It is no wonder then that so much of the machinery of tech organizations is centered around shipping.

But should it be? Especially given how much shipping itself has changed in the last couple of decades?

Here is a non-exhaustive list of problems that can occur when everything is oriented around shipping:

• Teams ship inferior or non-impactful things in order to say they shipped something
• Team A ships more than Team B and thus appears more competent, even though Team B’s mission is more difficult or process more rigorous
• Teams ship things that teach their company nothing
• Teams manipulate (or very liberally analyze) data in order to justify shipping
• Teams aren’t given enough runway to do great work because of the constant pressure to ship ASAP
• Team members are given (or not given) raises, promotions, or other praise because of how often (or seldom) they ship

Whenever I talk to design leaders from other organizations, I’m struck by how similar everyone’s challenges are. Over coffee with my friend Cap Watkins — Buzzfeed’s Head of Design — we talked about if there was a better way to measure progress than shipping.

Learning as a prime objective was what kept coming up. Organizations that learn the quickest seem the most likely to succeed over the long haul. This is not an original thought, for sure, but most companies don’t seem to have operationalized it formally.

Maybe shipping is actually just a subset of learning, or at the very least, in service of it. Put differently, shipping can be a great way to learn, but it’s not the only way, and it’s not always the best way. If all of that is true, how might we re-orient the development process around learning?

A provocative approach would be to prioritize learning as the most important regular deliverable of engineering/product/design teams. Let’s say you are a manager, executive, or anyone else interested in a particular product within a company. Here is the sort of progress report you are probably used to seeing from whoever is leading the team building the thing:

SEPTEMBER

• Launched movie recommendations
• Hired 2 engineers
• Fixed 30 bugs
• Went into beta with collaborative filtering
• Drafted product plan for internationalization

When written more with more structure, they can take the form of OKRs (Objectives & Key Results) or KPIs (Key Performance Indicators).

While useful in showing that the team isn’t sitting on their hands, it doesn’t really hold anyone accountable for what good all of that is doing for the organization. What caused the team to launch movie recommendations and what will that mean for the business? What will 2 more engineers accomplish? What is the impact of the bugs fixed? What do we hope to learn from the collaborative filtering beta and how will we know we should even launch it? What have we learned about internationalization in terms of how much bigger it will make our business or how much of an effort it will be?

A list like the one above is at best a tactical inventory, but at worst a veil that masks how little actual learning may be occurring. In other words, it may make you look like you’re moving forward (good!) at the expense of ignoring how little of a difference you are making (bad!). What if, instead of delivering something like that every week, month, or quarter, you delivered something more like this:

SEPTEMBER

• What we learned: Removing steps from our onboarding experience did not reduce user confusion. Instead, clearing up language such that users felt they were making progress resulted in the greatest gains (link to more details here).
• Cost to learn: One researcher, one prototyper, one week of calendar time, and $2000 in participant fees.
• Plan to proceed: Productionize new language within one month.
• What’s needed to proceed: Some internationalization help… we’ll outsource this.

 

• What we learned: We have entire tab in our app — Theaters — that only 1% of our users regularly use. Additionally, we have another feature — Friends — buried under a sub-menu, that almost half of our users use regularly. We aren’t sure what the effects would be if replace Theaters with Friends, but it seems like the right thing to do.
• Cost to learn: One PM, from one day of digging through data.
• Plan to proceed: Run an experiment swapping in a Friends tab in place of the Theaters tab and see what effect it has on metrics.
• What’s needed to proceed: We have no dedicated data scientist in our group. Would be great to have one, but short of that, if we could just get a day per week of someone’s time, we’d take that.

 

• What we learned: Our projects take at least 30% longer than they should because of an outdated build process that has too many dependencies. In addition to the cost in extra time spent, we have also lost engineers and designers due to this frustration.
• Cost to learn: We’ve been paying this cost in slow development and high attrition for at least two years.
• Plan to proceed: We just dedicated two weeks of an engineer’s time to investigate the issues and what it would take to fix. Our hope is to stack rank what’s easiest and most valuable to fix and then attack the list aggressively.
• What’s needed to proceed: We need air cover from executive leadership for probably about a month while we get this fixed. Meaning, we need to pause our current product work and not have to answer questions about why. This is important work, leverageable by the entire organization.

What we learned is really the key deliverable, and something potentially interesting to many people across the company. Cost to learn is a chance to optimize for and highlight efficiency, as spending a year of engineering time carries much greater opportunity costs than running some efficient, qualitative testing. Plan to proceed lets people know the outcome of the learning and how it affects the way forward. And finally, what’s needed to proceed spells out what a manager, executive, or anyone outside the core team can do to help.

This is a rough sketch and could use plenty of iteration and refinement, but one thing I like about it is that while there are plenty of legitimate and illegitimate excuses for not shipping, there is really no excuse for not learning. In other words, a team could spend an entire quarter (or much longer) shipping absolutely nothing, even though they are doing all the right things. However, if a team is not learning quickly and regularly, they are almost certainly doing something wrong.

I also like that a re-orientation around learning gets people thinking in an entirely different way.

“What’s the minimum we can ship with?” becomes “How might we learn X most quickly?”

“What do we want to release next quarter?” becomes “What is most important for us to learn about our product next quarter?”

“How can we ship more often?” becomes “How can we increase the pace of our own learning?”

None of this means you won’t also have to ask questions about shipping, but shipping simply becomes another way to learn… alongside research, prototyping, and many other methods. It’s still what you ultimately want to get to, but it’s more a by-product of the methodical learning you hold yourself and all teams within the company accountable for every week, month, or quarter.

Some of today’s companies who learn and evolve the quickest have surely already operationalized some of this sort of thinking, even if informally or by accident. If you’re reading this and you’re thinking to yourself “we already do all of that!”, then that is fantastic (and I would love to hear more about your process in the comments)! If, however, this sort of re-orientation sounds refreshing to you, start talking about it with your team and see what steps you can take to try it out on a project or two. I’m curious to hear what works best for everyone.

(This post also available on Medium.)

When deciding how to evaluate employees, these are often the things companies land on. It makes sense on its face. If a company’s goal is to, say, grow its customer base from X to Y in 12 months, what better way to align employees to that objective than to try and directly measure their contribution towards it? You worked on Project A and it singlehandedly got the company 20% closer to its goal? Congrats, you are judged to be a successful employee and you will likely enjoy everything that goes along with that.

But what if you worked on Project B — not even by choice but because you were assigned it — and it ended up being a failure? Your results were terrible, you didn’t move metrics, and your project had no impact. Then what?

Welcome to the controversial world of employee evaluation in product design & development.

I want to cover five aspects of this subject, and in doing so, provide an outline for others to use as they seek to improve processes at their own companies:

1. Why this matters
2. Decision quality vs. outcome quality
3. The four pillars we use(d) at Twitter Design and why (optional past tense because I left my role as Head of Design at Twitter earlier this year)
4. How to measure success
5. Putting your own plan into action

Why this matters

Treating designers, engineers, PMs, researchers, and any other employees fairly is an unspoken goal across almost every tech company. The only controversial part is how to actually make that happen. In order to do that, we have to recognize what the nature of a job in product development entails. Specifically, working well with others, taking risks, being creative, and embracing high-judgement failure.

Product development is a lot more like poker than chess. As an employee, you aren’t always in control of the hand you’re dealt, the other people at the table, or the unpredictable ways the process unfolds. It is your job to behave in a way that maximizes the chances of success. If you’re a designer, this may mean prototyping an interaction an exhaustive amount of ways. If you’re an engineer, this may mean writing throwaway code so you can test an approach before investing too much in it. If you’re a PM, this might mean yielding to your engineers and designers on something in the name of keeping team energy high.

In chess, a great player beats an average player 100 times out of 100. In poker, however, the “best” player loses all the time. The difference between good and bad poker players is how they behave. How they behave — or the quality of their decisions — is the difference between winning and losing over the long haul.

Decision quality vs. outcome quality

There is a phenomenon in tech called easy-to-measuritis which says that we tend to concentrate on the things we can easily measure rather than the things that are most important. For example, the best thing for our business may be happy customers, but in order to measure happiness, we may have to build a ton of unwieldy survey infrastructure, so instead, we just measure bodies coming through the door and use that as a general proxy for happiness. What then happens is we build things to optimize bodies coming through the door and we move that number whatever way we can, perhaps even to the detriment of customer happiness.

The traditional way of evaluating employees — based on things like results, metrics, and impact — is just another manifestation of easy-to-measuritis. We want objective, binary ways of evaluating people so that they are uncontroversial and unassailable, but what we end up with are objective, binary ways to measure the wrong things, or at the very least, things that employees are not in direct control of. Instead, we should be measuring decision quality instead of outcome quality. After all, how we behave is always 100% within our control.

Won’t you follow me on a personally painful sports tangent for a moment? Come along!

The worst sports moment of my life occurred on February 1, 2015, at 6:59pm. I was in Arizona watching the defending champion Seahawks play the Patriots, and after marching down to the 1-yard line with less than a minute left, the Seahawks called a pass play to Ricardo Lockette instead of a run play to the best running back in the NFL, Marshawn Lynch. If you pay any attention to football, you know what happened next. The ball was intercepted by undrafted rookie Malcolm Butler, preventing the best and most exciting team in the NFL from winning a second straight Super Bowl.

That was the worst play call I've seen in the history of football.

— Emmitt Smith (@EmmittSmith22) February 2, 2015

Reading the tweets and other reactions after the game, I had never seen such universal condemnation for a play call. Commentators, coaches, players, fans, and anyone else who had watched a down of football in their life chimed in on the epic stupidity of our offensive coordinator and head coach. My own hatred and disbelief of the call lasted several months as well until I read something really interesting: a FiveThirtyEight.com statistical analysis of that fateful call. The TLDR version is essentially:

1. NFL teams had scored 125 rushing touchdowns from the 1-yard line that year and two attempts resulted in turnovers.
2. NFL teams had thrown 66 TD passes from the 1-yard line that year and ZERO attempts resulted in turnovers.
3. The Seahawks final playcall was either only 0.3% worse or 3% better than a run, depending on certain assumptions.
4. New England’s decision to *not* call a timeout was, statistically a much worse decision than the final pass.

… and yet, the Patriots won the game, Seahawks coaches generally looked like buffoons, and New England coaches looked like geniuses. As reporters descended down upon Seahawks coach Pete Carroll to find out what he was thinking, one thing he said repeatedly didn’t sink in for me until a few months later after reading all of the analysis. He said:

“It wasn’t the worst decision. It was just the worst outcome.”

… and in fact, it was arguably a pretty good decision, or at least a defensible one.

As with employee performance, it’s easy, and frankly lazy, to judge outcomes. Only upon thoughtful evaluation can you judge decisions and behaviors, which — as in poker, football, and product development — maximize your chances of success over the long haul.

Ok, no more sports! Believe me, that hurt me a lot more than it hurt you.

The four pillars we use(d) at Twitter Design and why

When we created our career paths and promotion process for Twitter Design & Research, we followed many of the principles mentioned above: reward behavior over outcomes, emphasize the importance of teamwork and execution, and keep everything within each employee’s control. Here are the four equally weighted pillars we settled on:

1. Getting things done: Pretty simple. Do you do what you say you are going to do? Do you go the extra mile to complete work that needs completing? Are you where problems go to die? This pillar is both a measure of dependability and prolificacy.
2. Creating strong relationships: Product development is a team sport. As I mentioned in Three Years in San Francisco, Intelligence X Collaboration = Results. Note that the relationship is multiplicative. If either I or C nears zero, so does R. Unless you are running the world’s worst interview process or physically sucking brain matter out of your co-workers, I is never really in danger of hitting zero. C, however, always is. If you score highly in this pillar, not just your direct colleagues will love working with you, but your cross-functional colleagues especially will. Know that designer who all engineers want to work with? That’s this woman.
3. Improving the team: One of the benefits of working at a company with other great designers, engineers, PMs, and researchers is that the sum can be a lot greater than the parts. Not only that but by virtue of being around so many talented teammates, your own career growth can happen almost automatically without having to spend nights and weekends learning new skills. We encourage people to make their teammates better by doing things like brown bag sessions on prototyping, brainstorming, and other important skills. Additionally, we encourage people to proactively help their teammates out on projects even if the project is not their personal responsibility. Improving the team can come in many other ways, including recruiting new teammates, but the point is to be a great teammate above and beyond being a great designer, engineer, etc.
4. Technical skills, empathy, and vision: These are the individual skills that most people initially assume are the only keys to success and promotion. We purposefully made them account for only 25% of the total formula to stress how important the other elements are. These are also the skills that are most customized to Design & Research. If you want to adapt this entire framework to PM, Eng, or any other function, you could probably leave the first three alone and just change this one pillar a bit.

How to measure success

Ok, so now that we have our four pillars, how do we measure success against them? This is where some people are going to get uncomfortable. The answer is by soliciting opinions from peers, managers, and anyone else who works with the person being evaluated. Isn’t that subjective though? Yes, yes it is! It’s subjective, but clearly specified and full of agency. You may disagree with a person’s assessment of you (which is why multiple people give feedback), but you should never feel like you either don’t know what’s expected of you or that you aren’t in control of the associated behaviors.

I will also note that as a manager, if you’ve hired and coached well, people should naturally do well in all four of these areas. If you receive feedback to the contrary, it’s your responsibility to investigate further and get to the bottom of the whatever is going on (if anything).

Putting your own plan into action

One of the reasons the switch to an explicitly behavior-based evaluation system was so well received was that we were transparent throughout the process of creating it and included diverse perspectives all along the way. We solicited feedback from men and women, from senior employees and rookies, from people of different races, and from people outside the department as well. Through that inclusive process, we not only greatly improved the framework, but we also created a feeling of collective ownership before it was even ratified.

So, yeah, if you are going to change the way your team gets evaluated, don’t just pass commandents down from a mountain. Get everyone involved in the journey.

One other piece of advice: solve this for your department first and see how it goes before entering a company-wide holy war on the subject. When we wanted to try this out at Twitter, we simply included our wonderful HR partners in the process, got their blessing to give it a shot, and then just made it happen. While I hope that the entire company soon evaluates employees the same way we do, we wouldn’t have gotten anywhere if we insisted everyone blindly do things the way we were proposing. As in product development, it’s often smart to start small.

Alright, so that’s the framework! Take freely from it whatever you’d like. It’s one of the things I’m most proud of improving during my time at Twitter. Like good design itself, it’s aimed at doing the only thing design actually can do: increase the chances of success.

(This post also available on Medium.)

It was go-time now though.

A drawn-out dance of interviews over the course of six months resulted in an offer to move down to the City and join Twitter to lead its Design team. My wife and I had never considered leaving Seattle before, but the opportunity to join Doug, Dick, and a few other people I knew designing a product that reached hundreds of millions of people was exactly the sort of thing you drop everything for.

“We can always hightail it back up here the second things go to hell.”

There was always a happy escape route — something that ultimately made living in San Francisco for the past three years considerably less stressful. Thousands of San Francimmigrants from places like Romania, Bangladesh, Pakistan, and less privileged area of America don’t have this option. For many new residents of the Bay Area, the thought of going back from whence they came is inconceivable.

After signing in blood with a start date in late October 2012, the first order of business was moving my ass down solo for a few weeks while my wife quarterbacked a plan to move all of our stuff out of our house, rent the place to a friend, and haul our life down to the the Land of Opportunity.

Worst case, I would hit the eject button in those first few weeks… if I couldn’t stand the City, if either of us had a sudden change of heart, or if there was something terrible about Twitter that had been kept from me.

My first memory of moving down was sitting in my temporary apartment in Dogpatch listening to the Giants win the World Series a few blocks down the road. I probably should have adopted them as a secondary team that week, given that — as a National League team — they aren’t competitive with the Mariners, and as a non-functioning baseball organization, the Mariners aren’t competitive with anyone. Two years later, the Giants would win another title, and having doubled down on my no-carpetbagging policy, I missed that champagne as well. And let’s not even talk about the Warriors. Seattle doesn’t even have a basketball team anymore, the Warriors are super fun to watch, and their head coach babysat me when I was a kid. Not to mention, Steph Curry is from Davidson College, the best named college in the country. But alas, no carpetbagging.

The first few weeks in a large Bay Area tech company are humbling. Throngs of people who are all used to being the best in their class and the smartest in the room, and I always felt like the dumbest. I’m a reasonably confident person and it took me several weeks to even feel comfortable speaking up in a meeting.

“Am I supposed to already know the answer to this question I’m about to ask?”

“What the hell is a precision-recall calculation?”

“How do I get a word in edgewise around this table?”

I took the baton of running Twitter Design from a good friend of mine, Andrei, who helped grow the team to about 20 people and also helped recruit me. There was a lot to build on, like a fantastic nucleus of designers and a small research team, but also plenty of opportunity to improve. Morale was volatile, career paths needed some development, and we needed to figure out how to move from being a small, centralized design team to a much larger one, physically embedded throughout the company. Organizational growing pains.

There is so much to write about what happened over the following three years, but I’m conflicted by a few things:

1. Part of honest writing is being candid about both positives and negatives, and every time I think about disclosing the negatives of my time at Twitter (of which there are plenty), it somehow feels unprofessional. Part of what makes the Bay Area the Bay Area is keeping your rose-colored glasses on even when it’s raining cats and dogs. Make no mistake: Twitter treated me personally very well, but it sometimes felt more like a game of Survivor than what I am used to. I feel comfortable writing a balanced post about all of this because I have no goal other than to put some thoughts that have been trapped in my head into writing.

2. My opinions are colored by *many* biases, including: anchoring, attentional bias, belief bias, choice-supportive bias, confirmation bias, curse of knowledge, declinism, focusing effect, hindsight bias, illusion of control, illusory correlation, not-invented-here, omission bias, optimism bias, pessimism bias (yes, you can have both!), pro-innovation bias, reactance, reactive devaluation, selective perception, survivorship bias, triviality, actor-observer bias, group attribution error, and projection bias. In case you’re wondering where that list came from, there’s a whole page of interesting biases on Wikipedia.

   In addition to those biases, there is one that I’m sure has a name but I can’t find anywhere: the tendency to falsely correlate how much you like and respect someone with how effective they actually are at their job. Unless someone points me to what this is called, I will just coin it “Affective-Effective Bias”. Over the years, I have realized that I am 1000% guilty of this. Life is too short to work with assholes, and if you are an asshole, my brain will concoct all sorts of reasons you are probably not the best person for the job. Conversely, if you are kind-hearted and emotionally intelligent, I will go out of my way to help you succeed in almost any situation. This is a weird bias in that I recognize its potentially negative effects, but my world-view is aligned with it so that’s how I roll.

3. There are several topics I absolutely do want to write about but they need their own posts:
   • Rewarding behaviors vs. outcomes, and how we evaluate designers and researchers.
   • How we approached diversity and went from 80/20 male-female to 50/50 in less than a year.
   • The positive and negative effects of using data in product development.

   If you have other requests, please DM me @mikeindustries.

Anyway, back to the program…

It doesn’t take long for your perceptions of large tech companies to change once you begin working at one. I knew there would be a ton of smart people at Twitter, but I didn’t realize it would be pretty much everyone at the company. I also thought that everyone who had secured a position that involved managing people or products had demonstrated experience successfully managing people or products, and that was just not true in many cases.

Let’s talk about product management first and then we’ll get to people management.

There is a contentious ongoing debate in our industry about what the requirements and role of a product manager should be. One side says they must be deeply technical (i.e. ex-engineers), while the other says they needn’t be. I’m told the deeply-technical mindset came from Google, where one day a long time ago, they decided they needed a PM role at the company so they took some of their best engineers who were already widely respected at the company, and made them PMs. Makes total sense, especially considering the early problems Google was trying to solve (mainly search quality), but unfortunately it has caused a wave of copycatting in Silicon Valley that is bad for products, bad for diversity, and bad for business.

First, because “being deeply technical” often uses a computer science degree as a proxy, many women are not considered for product management positions they are absolutely qualified for. This is industry-wide and not a problem specific to Twitter. In other words, if you are a hiring manager and your first pass filter is to see if an applicant has a C.S. degree, the majority of applicants to make it past this filter will be men. If instead, your first pass filter is to determine what sorts of product decisions applicants have been in charge of in the past, your field will probably be less skewed. In my mind, a woman with a communications degree from a state school who has managed email marketing for a political campaign is more likely to be a good product manager than a man with a computer science degree from MIT who has managed release planning (or managed nothing!).

In descending order of importance, here is what makes a good product manager:

1. Empathy. For customers, direct teammates, and others around the organization. This is actually an area where a C.S. degree can absolutely help because it’s a head start on having empathy for the engineers on your team. That said, it’s the empathy itself that matters… not the C.S. degree.
2. Communication skills. Almost every problem you run into at work can be traced back to communication issues, and a great PM should be the gold standard in how we communicate with each other at work: respectfully, candidly, and in a way that makes the entire team better. Charisma is a part of this as well. I think it’s easier for a designer or engineer to succeed without a ton of charisma, but a large part of being a great PM is an ability to motivate and inspire people with your words and your energy. Additionally, it’s your job to be a “heat-sink” when conflict arises between team members or elsewhere in the organization (credit to @sippey for introducing me to that term).
3. Business sense. You need to be good at identifying and framing problems to solve, prioritizing them according to impact on the business, and breaking them down so they can be tackled as quickly and efficiently as possible.
4. Taste. I put this last because sometimes it’s frankly optional. If what you’re managing doesn’t actually go in front of customers in a way that is noticeable to them, taste doesn’t matter as much. You can also often rely on your designers, engineers, and other partners to help lead the way on this. There is, however, a palpable amount of extra respect you’ll get from your team if they perceive you as someone who values taste (even if it’s not your own).

That’s really it. I wouldn’t argue with someone who wants to re-arrange the order of those, but it’s just silly to me that when I read some PM job ladders from inside our industry, the word “empathy” doesn’t even appear.

The best PMs at Twitter are SO good at all of these things, and in some cases, not very technical at all. Their teams fight for the opportunity to continue working with them. There are also great ex-engineers and designers who, as PMs, embody these qualities, but it’s important that a good interview (and promotion) process tests for the qualities themselves… not some other marker like a computer science (or design) degree that measures a different thing.

And finally, let’s dispense with the oft-given advice that PMs should think of themselves as “mini CEOs”. There are so many things wrong with this advice that it’s hard to know where to begin. Chiefly:

• Employees may join a company specifically to work under the leadership of the actual CEO, but they rarely join to work with/for a specific PM.
• A CEO is usually free to enable the success of their team (the whole company) by any means necessary, even if it involves damaging things outside the organization itself. As a PM, you are a cog in the organization, and much of your job is to enable success inside and outside your team, by virtue of your actions.
• The term CEO is so loaded with preconceived notions, that it’s just not a safe place to even start your job description.
• Most PMs will never go on to become CEOs, let alone successful CEOs, and the fact that as a PM, you may have even been a CEO beforehand, that doesn’t mean you know what it takes to operate successfully as a PM. Some of the worst PMs I’ve seen, in fact, were CEOs in the past. This logic is true for designers and engineers too, by the way. If you’ve been a Creative Director for an agency with 5 designers, that doesn’t mean you are qualified to be a Designer or Design Manager at a larger company. Context matters.

… and on and on.

Alright, enough about PMs. I don’t mean to pick on them, and I worked with some spectacular ones at Twitter. I just feel like of all the disciplines I worked with, that discipline had the widest range of effectiveness and — industry-wide — could use the most rethinking and codification.

On to people management.

One of my favorite rules at Twitter — at least within Engineering, Product, and Design — is that there is no such thing as a “promotion into management”. If you want to become a manager of people, it is always a lateral move. For example, if you are a senior designer and you decide you want to manage people instead of pixels, and leadership deems you ready for it, you can become a Design Manager. That move, however, does not “level you up” in the system, nor come with a pay increase, nor put you on any sort faster career track. You’ve simply moved from concentrating directly on product problems/opportunities to concentrating on people problems/opportunities. I believe some other companies have this rule as well, but it’s really fantastic for what it encourages: people should do the type of work that is most fulfilling to them and most valuable to the company. A fantastic I.C. (Individual Contributor) is just as valuable as a fantastic manager, and the system should reward and encourage both career branches equally.

One of my least favorite things to deal with, however, was the lack of an “emotional intelligence” requirement. The definition of emotional intelligence I use may be a little more liberal than most. To me, emotional intelligence means that someone not only picks up on how teammates are feeling, but they also care deeply about running a team in which people are emotionally fulfilled and inspired.

Some people are almost born with emotional intelligence. They have it by the time they get to high school. Others need to spend a bunch of time in the workplace getting experience with all sorts of conflicts and original situations before they have it. And still others will simply never have it, or at least they won’t have it at a level which qualifies them to be what I consider a great manager. You’ve probably met all three of these sorts of people and can pick out the last group pretty easily.

I believe that every organization should make emotional intelligence a requirement of being a manager or executive leader. It should be no less a requirement than ability to recruit, inspire, multitask, prioritize or any other thing we typically require in our leaders. We should interview specifically for it and we should categorically reject as candidates those who show no aptitude for it. Some amount of “learning on the job” is of course ok, but where I struggled the most during my time in San Francisco was dealing with people who showed no ability or desire to balance happiness of people with visible output. False dichotomies like “we can’t optimize for happiness” make the problem even worse. That sort of thinking pre-supposes that somehow happiness is in conflict with execution. It also implies that the whole world is a math problem, which I strongly disagree with.

When people say they aren’t happy, it usually doesn’t mean they want to be coddled with things like unusually short work hours, extravagant food, or other things that are bad for the business. It means they aren’t happy with their direct working environment and the impact they are having. It could mean they are frustrated by how long it takes to push code to production. It could mean they are frustrated by designers who aren’t showing their work early and often enough. Or it could mean no one on the team has any faith in the PM. Fix those things and happiness will come with it. Here’s the difference, though, in someone who has and doesn’t have emotional intelligence: the former will pick up that these problems exist from the team, take their emotions seriously, and dig in to help fix. The latter will largely discount the unhappiness and, at worst, attribute it to the person who is unhappy instead of the root cause.

My perception is that much (but not all!) of Silicon Valley is riddled with these sorts of people. Smartest in their class, impressive degrees, ability to ace whiteboard interview problems, but very little ability or desire to relate to teammates or even customers as human beings. It’s excusable to make a few wrong calls in hiring these sorts of people, especially at junior levels, but no one should ever be promoted or stay in their position very long without demonstrating this ability. I’m not going to get any more specific because this isn’t a problem with one person or even one company. It’s a problem with the industry, and it’s driving all the right sorts of people away.

Alright, that’s it for people management. More posts on that subject will surely come later.

We began thinking of heading back up to Seattle a little less than a year ago. There was great work coming out of EPD (Engineering/Product/Design), our team had reached 50/50 gender equity and were on our way to better racial diversity, our attrition rate was among the lowest in the company, Jack was coming back to lead, and I found myself wondering why I felt so much like leaving.

When a designer friend of mine, Geoff, left Twitter a few years ago, the reason he provided really stuck with me. He said he was unable to approach problems anymore with a Beginner’s Mind. Instead of meeting each new challenge with an open mind and fresh enthusiasm, he let his past experiences limit his creativity and his positive outlook. In other words, when you’re the person in the room silently thinking “I know how this ends” or worse yet failing to put your best energy forth, it’s probably time to move on.

That was beginning to be me.

While we’d grown to really love San Francisco as a place to live, the geographical aspect of leaving wasn’t very difficult. Yes we’d miss the year-round mostly sunny weather, the abundance of interesting companies, and the walkability of the city, but we definitely wouldn’t miss the terrible bread (Tartine, Josey Baker, and Noe Valley Bakery excepted), cold nights, and the inexcusable yet entirely fixable housing problem. Truth be told, the thing I knew I’d miss most about the City was the public transportation. People love to bitch about BART and MUNI, but they are such an amazing asset to San Francisco, hampered only by the fact that they aren’t as big as they were originally planned to be. San Francisco is what I would call a “car optional” city. If you’re going downtown or anywhere else BART or MUNI service, you don’t need a car, and it is in fact slower and more expensive to use one. If, however, you want to take a nice day trip to Half Moon Bay, Mount Diablo, or any number of other amazing locations around the Bay Area, your car is your best friend.

Seattle royally screwed up its chance to build a truly robust public transit system 45 years ago. As a result, it is, like most other cities in America, a “car mandatory” city, for the most part. In the three years we’ve been gone, traffic in Seattle has gone from bad to almost L.A. bad. It’s a self-inflicted wound that I hope heals eventually, but it’s still painful and getting worse.

The hardest part was leaving my team, who I consider to be the best group of designers and researchers I’ve ever worked with. 90% of what I learned at Twitter I learned from them. The second hardest part was saying goodbye to Jack, a empathetic leader who puts people first and is leading real change at the company through inspiration and example. Like Dick before him, he’s an extremely hard worker and uniquely qualified to lead the company at the time he is taking over.

As I write this, it’s now been almost 90 days since we left Twitter and returned to Seattle, but it already feels like a year. As we return to normalcy via an extended period of time off, only now can we reflect on what lessons three years in San Francisco delivered. I’ll close this rambling post by listing the three lessons I value most:

1. The Bay Area is a silly place, but it is in fact silly by design. My favorite Venn diagram (from a prominent investor) perfectly illustrates this:

   

   In other words, most of the best ideas sounded stupid at one time, and if a good idea doesn’t sound stupid, many companies are probably already working on it. This diagram is why you probably find almost every startup idea you hear about to sound ridiculous. It probably is ridiculous, but the Valley is a place where investors embrace this dynamic and give entrepreneurs Other People’s Money to see if they can land their idea. Jeff Bezos (a card-carrying Seattleite!) had a great quote in his latest shareholder letter. He said:

   “One area where I think we are especially distinctive is failure. I believe we are the best place in the world to fail (we have plenty of practice!), and failure and invention are inseparable twins. To invent you have to experiment, and if you know in advance that it’s going to work, it’s not an experiment. Most large organizations embrace the idea of invention, but are not willing to suffer the string of failed experiments necessary to get there. Outsized returns often come from betting against conventional wisdom, and conventional wisdom is usually right. Given a ten percent chance of a 100 times payoff, you should take that bet every time. But you’re still going to be wrong nine times out of ten. We all know that if you swing for the fences, you’re going to strike out a lot, but you’re also going to hit some home runs. The difference between baseball and business, however, is that baseball has a truncated outcome distribution. When you swing, no matter how well you connect with the ball, the most runs you can get is four. In business, every once in a while, when you step up to the plate, you can score 1,000 runs. This long-tailed distribution of returns is why it’s important to be bold. Big winners pay for so many experiments.”

   (Emphasis mine)

   I like criticizing ideas on the internet as much as the next person, but the next time you hear yourself doing this, ask yourself if you are just expressing conventional wisdom. If you are, congratulations, you are probably going to end up being “right”. But you are also not really saying anything the average human being isn’t already thinking. The Bay Area is a great place to work in that it’s a collection of people who don’t mind looking silly for awhile in pursuit of something insanely great. Most end up failing, but that is both predictable and perfectly ok. What’s less encouraging is the over-investment in “solution in search of a problem” services or things that make rich people’s lives even easier — like this fucking $700 juicer, for instance — but that’s another story. Hey, who knows… maybe one day it will deliver sustenance to underserved areas of the world or the pressing technology will have some sort of unrelated beneficial use.

   I don’t think the Bay Area is the only place to do great work in engineering or design by any stretch of the imagination, but it does seem like a place everyone should spend at least a year if they can make it work. Like me, you may find it a better temporary stop than a permanent home, but it’s an energizing place to do great work and meet many of the people you will go on to do even better work with later in your life.

2. Team chemistry is the most important thing to get right when building companies and products — not brainpower. For the math fans out there, think of it this way: Intelligence X Collaboration = Results. Intelligence is never really in danger of going to zero, but Collaboration is always on a hair trigger. Whether you are talking about the engineers, designers, PMs, researchers, or anyone else doing the actual work, the managers in the middle clearing paths for them, or the executives at the top setting strategy, you need alignment up, down, and across in order to get anything great done. I’m not talking about the sort of tactical alignment that lets people agree on things like colors, deadlines, and algorithms. I’m talking about agreement on values, roles, and how people should treat each other. People will arrive at your organization with all sorts of habits they’ve picked up elsewhere in their career. Maybe they are engineers who have never worked with a designer beyond getting icons produced. Maybe they are designers who are used to having “a monopoly on taste” within their cross-functional team. Maybe they are PMs who have never used primary research before. Or maybe they are researchers who have never been expected to produce an opinion. If you don’t have a playbook that lays out how this works at your company, the loudest voices in the room are going to determine it on their own, and in my experience, the loudest voices are rarely the wisest voices.

   It’s been gratifying to read about Google’s latest research on how to create successful teams. Turns out most of the things they (and by extension, many other companies in the Bay Area filled with ex-Googlers) thought went into creating successful teams were not instructive at all. Things like advanced degrees, proficiency in solving interview questions on whiteboards, and extroversion simply didn’t add up to team success. Instead, it was five other things: psychological safety, dependability, structure & clarity, meaning, and impact — with psychological safety being far and away the most important. Psychological safety, in an organizational sense, is the feeling that it’s ok to take risks and be vulnerable in front of each other. If you put a group of experienced stage actors together, they’d probably be great at this already. However, put a group of strongheaded engineers, designers, and PMs together, and this is something you need to not only actively work on but essentially legislate, as Google is likely doing right now. “Assume your colleagues are smart and have good intentions” is a popular piece of advice, but it’s really not enough. Intelligence and benevolence do not tell us how to work together, and at worst this assumption can cause us to overlook other problems, like whether someone’s approach is actually good for the product or the team.

   If there’s one thing I regret most from my time at Twitter, it’s that I don’t feel I made enough impact in improving and codifying how teams work together. Clearly it’s a very tough problem, as many well-regarded companies are still finding out, but if I could wave a magic wand and increase my impact in one area, that would be it.

3. Finally, working in the Bay Area tech scene taught me about privilege, how it shapes industries, and the importance of doing your part to actively level the playing field. There will be another post dedicated to this, but I will just say that I don’t think everyone in tech has internalized the problem yet.

   In my mind, there are five stages towards understanding diversity, inclusion, and privilege: ignorance, denial, acceptance, caring, and action. I encountered people all along this spectrum, and in fact, when I got to Twitter, I would probably put myself at the first stage. The first time someone referred to me as “privileged”, I felt a bit defensive, as although I grew up an upper middle class white male, I never asked for any sort of leg-up. I think this is an important detail when we talk about how to level the playing field in the workplace: it’s not about scolding people for privilege. It’s about teaching them the compounding effects of it, and getting them to want to actively change the way the world works. In other words, until we know otherwise, we should assume ignorance and shape our approach accordingly.

   The most important outcome, however, is to get to the “action” stage. If you are in a position of power and you claim to care about diversity, you either care enough to directly invest your time, energy, and budget or you don’t care at all. There is no useful middle ground. At the end of the day, teams tend to do what they think is important to their leaders, and if you aren’t taking visible, enthusiastic responsibility for your team’s diversity, your team members won’t either. It’s great to see companies like Slack building these values and expectations in from the very start and setting an example for other tech companies that meteoric growth and workplace diversity can go hand-in-hand.

   There are things I’m proud of and things I’m not proud of when it comes to what our department has accomplished over the last few years, but standing above anything related to our craft is the responsibility the team took in building empathy for women and minorities in our industry, having honest conversations about where we needed to improve, and finally diversifying our team substantially. I’m even more proud that it was thoughtful team members — female designers and researchers specifically — who rubbed together the sticks to get the fire going. There is still so much work to do, but I’m proud that our team is leading by example.

To close this 5136-word catharsis, I want to thank Twitter, the Bay Area, and everyone who put up with me for the last few years. There are talented, creative misfits all around the world who are doing fantastic work solving important problems, but only in San Francisco is the atmosphere so audacious, so chaotic, and so beneficially uncomfortable that more creative destruction is guaranteed for years to come.

As for me, I’m done being uncomfortable for a little while. The last few months of baking bread, learning guitar, and jogging around this beautiful city have reminded me how much I value overall quality of life… and for overall quality of life, there is no better place in the world than Seattle in the summer.

(This post also available on Medium.)