What I’m Writing

Machine Learning and Cover Songs

There’s nothing like a great cover.

You’re rekindling angst at a Pearl Jam show and without any warning they go right into a Beatles song. You recognize some David Bowie lyrics on Spotify, and you discover it’s an unrecognizable version of Let’s Dance by M. Ward. You listen to Tiny Cities by Sun Kil Moon several times before you even realize it’s an entire album of beautifully fermented Modest Mouse songs.

How often have you thought to yourself, I would love to hear this person sing this other band’s song in their own style? For instance, I wish I could listen to Mike Doughty sing just about anything.

Over the past year or two, we’ve started to see artificial intelligence begin to approximate that dream (or nightmare, depending on your perspective). First it was eye-opening deep fake videos of past presidents appearing to say things they never said, but now it’s moved on to much more creative and cool endeavors like OpenAI Jukebox. You should read the full description on the site, but essentially they are training models to identify everything that goes into a song: instruments, lyrics, musical style, and a whole lot more. The models are primitive for now, but even at this early stage, they can start recombining things in interesting ways like having Ella Fitzgerald sing a Prince song but in the style of folk rock.

I spent a good part of the weekend messing around in Jukebox, and it’s mesmerizing. It really feels like the beginning of something big, and just as excitingly, something that could get orders of magnitude better within only a few years.

When you listen to it, it almost feels like the first words of a child… or if you prefer, the first song from Jimmy Page.

A lot of the stuff in the library is pretty rough, but here are some of the most interesting ones I found:

Everything feels very Frankensteiny right now, but imagine a few years from now when these techniques are improved and expanded. We may reach a point where there is a virtually unlimited universe of concert-quality covers you can create with just a few taps. As a music lover, this is super intriguing, but on the other hand, I wonder how musicians will feel about it. And will their opinions change based on whether we can find a way to monetize it generously for them? I could see some artists rejecting this sort of thing outright because it’s not real music in the traditional sense, and I wouldn’t blame them. But what if you told them that every time their voice was mixed into another song, they made a royalty off of it? That might change some opinions.

This is going to be a really fun space to watch closely over the next few years. Until then, I leave you with another great cover: Metallica’s Orion — by Rodrigo y Gabriela. Incidentally, the header image for this page is from their Masonic Auditorium show in 2015. Pure luck but probably the best photo I’ve ever taken.

A Quarterback-Only Strike: How NFL Players Can Win This Labor Deal

I have never been less qualified to write about anything than I am about NFL labor negotiations, but I had a crazy idea a little while ago for how NFL players can win their labor dispute with owners and I want to get it out there for battle-testing.

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.

Minimum Viable Connectivity

I remember about 15 years ago — before the launch of the iPhone — thinking quite resolutely that internet-connected phones were just a really unexciting transition phase between the desktop internet and immersive technologies like contact lenses and brain implants. We knew where we already were: amazing high bandwidth experiences on the desktop, and it seemed pretty clear where we were going in a couple of decades: even better experiences with no visible hardware whatsoever.

The new class of experiences on mobile phones at the time, however, was uninspiring. Palm Treos with barely functional browsers on them. Blackberries that handled email but little else well. T9 keyboards that were a pain to use. Barely any designers wanted to work on this stuff. It wasn’t very fun to create, use, or even tell anyone you worked on.

When the iPhone came along in 2007, it was the first mobile device that was fun to design for and fun to use for a wide variety of things. As it grew more and more useful, I began to think of internet-connected phones as quite a bit more exciting but still ultimately a transition state to full cyborg land. It seems inconceivable that in 10 or 20 years, we will still be staring down at these glass rectangles instead of directly at the world with whatever augmented reality experiences we choose in between.

As phones have gotten more comically large and the services on them more tragically addictive over the past few years, I’ve found myself wondering if there is more value in letting some of this connectivity go. Clearly smartphones provide a lot of value for us, but what is the true cost of all this convenience? Being able to receive a text from your spouse while you’re at the supermarket is valuable, but the same device that delivers you that text can deliver a social network notification while you’re driving that ends up killing you or others.

Attempting to quantify the large and small harm caused by smartphone use is a big project better suited to places like Tristan Harris’ Center for Humane Technology, but you don’t need to quantify it to admit it’s doing you some amount of harm.

There is no shortage of advice about how to make your phone less addictive. Turn off a bunch of notifications. Flip on Do Not Disturb. Use Black & White mode. Delete social networking apps. It’s all good advice, but for me, having that giant, heavy glass brick in my pocket is a constant reminder of what’s at my fingertips.

What I’ve really grown to want is less at my fingertips.

Minimum viable connectivity.

Wherever I happen to be, I want the least amount of potential digital distractions and appholes around me. It’s no different than the concept of eating healthier. When you want to lose weight, you don’t keep a bunch of junk food in your pockets and just promise to never open it. You remove junk food from your house completely.

Until recently, there was no great way to stop carrying your smartphone with you without giving up a ton of benefits. Over the past two weeks, however, I’ve begun using an Apple Watch without a phone almost all day long, and it’s been great. It’s introduced exactly the amount of digital friction I need in my life and I don’t imagine going back to hyper-connected smartphone world anytime soon.

“The best way to guarantee success is by preemptively engineering systems to reduce friction for positive habits, and increase friction for negative ones.” — Craig Mod, from the great piece I linked to above

I love that I am still generally reachable by phone or text when I wear it. I love that I can still navigate with maps. I love that I can track my runs without third party services and listen to podcasts along the way. I love that I can see when it’s about to rain.

And I love that that’s about all I can do. I don’t mind that texts are a little harder to send. I don’t even mind that there’s no camera. If I’m on vacation in an interesting place, I will surely take my phone, but do I really need to be taking more photos around town? Probably not. This is the point many people will break with me on this whole strategy, but try it. You may be surprised.

In terms of things I don’t like about about this experiment so far, it really just comes down to a couple of flaws with the watch itself: the LTE radio is pretty spotty and the Apple Podcast app is a usability disaster, both on the phone and the watch. Because the radio is weak, you really need to make sure anything you want to listen to is downloaded already, and because the apps are so bad, it’s very hard to ensure that actually happens. You’ll generally have some podcasts downloaded and ready to listen to but they just aren’t always the ones you expected. ¯\_(ツ)_/¯

Even with those problems, I still feel great about this less-connected road I’m going down. Somewhat surprisingly, I don’t even feel like I’m missing out on anything.

The hyper-connected future will probably still happen, but the form it will take doesn’t feel so inevitable to me anymore. I’ve learned in these two weeks alone that I don’t actually want every distracting digital experience in the world at my fingertips. I only want what is helpful and stays out of the way.

The last time I wore a watch was in high school, and I distinctly remember how excited I was to finally get a cell phone my junior year.

27 years later, I’m just as excited now to do the opposite.

A Year of Working Remotely

It’s been exactly one year since I joined InVision, and after learning the ropes of remote work at an 800+ person all-remote company, I wanted to share some thoughts on how placelessness may affect the way we work in the future.

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.

Read more…

Superhuman’s Superficial Privacy Fixes Do Not Prevent It From Spying on You

Last week was a good week for privacy. Or was it?

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.

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:

Read more…

Superhuman is Spying on You

Over the past 25 years, email has weaved itself into the daily fabric of life. Our inboxes contain everything from very personal letters, to work correspondence, to unsolicited inbound sales pitches. In many ways, they are an extension of our homes: private places where we are free to deal with what life throws at us in whatever way we see fit. Have an inbox zero policy? That’s up to you. Let your inbox build into the thousands and only deal with what you can stay on top of? That’s your business too.

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:

A log of every time someone has opened your email and what location they opened it from.

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:

Read more…

Newsletters I’m Digging

Reading Craig Mod’s excellent piece The Future Book is Here, but It’s Not What We Expected got me thinking more about newsletters. I’ve never been a big consumer of newsletters, mostly because I still use RSS regularly and don’t really need more stuff in my inbox.

Then the other day I happened to find the first new blog I wanted to subscribe to in years, and lo and behold, Aaron doesn’t even have an RSS feed! Just an email newsletter.

So I added Aaron’s newsletter to a dedicated newsletter app I’m testing called Stoop and now we’re golden.

Although I still use Twitter and RSS feeds for finding interesting links, there’s something nice about a well-curated newsletter that aligns with your interests. I still don’t subscribe to many of them, but my favorites so far are:

  • Dense Discovery: A weekly list of mostly design-oriented interestingness from Kai Brach. I probably click on over 50% of the links. Very high signal-to-noise ratio.
  • Sentiers: A weekly list of articles related to how technology is reshaping society, curated by Patrick Tanguay.
  • Axios Edge: 99% of “news” published every week simply does not matter. Axios Edge from Felix Salmon shows you only what does matter, why it matters, and what it might mean for you.
  • Recomendo: A weekly list of six practical, nerdy product recommendations every week from Kevin Kelly, Mark Frauenfelder, and Claudia Dawson.
  • Cumberland Advisors: If you are sickened by the clickbait at mainstream financial sites but still want to know what developments in the world mean for the markets, David Kotok’s emails from this list are particularly informative. The other authors can be a little too niche.
  • The Howard Marks Memo: Marks is famous for his financial memos, which generally only come out a few times a year. Very long, very infrequent, and very well-written.

If anyone has any other recommendations, please feel free to leave them in the comments! I reserve the right to delete anything that looks spammy, self-promotional, or low quality, however. Only the good stuff, please! :)

Clocking Back In… at InVision!

As a designer, I owe my entire livelihood to tools.

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!

That’s me at my last job… talking about my next job.

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.

Still miss you, @design fam! Glad you’re doing well!

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.

Got my green-screen video conferencing background all dialed in
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.

Remember this fun tool from the ’80s? LOAD “*”,8,1

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.

Design-Driven Companies. Are We There Yet?

It’s fashionable these days for companies to proclaim their commitment to great design.

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.)

An Epitaph for Newsvine

Today, the creation I am most proud to have brought into the world disappeared from the internet.

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.)

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