What I’m Writing

How To Ask for the Truth

“I’m really sorry to hear you are leaving. I wish I would have known you were unhappy.”

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.

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The Five-Tool Designer

As someone who has managed and worked with designers for most of my adult life, I get a lot of calls from people looking to check references on someone I’ve worked with or find out from me if there are other designers they should be talking to.

When I think about the range of critique I’ve provided in these situations, the term I always use to describe the very best designers I’ve ever worked with is five-tool designer.

Five-tool player is actually a baseball term used to describe someone who can hit for average, hit for power, run the bases, throw, and field. It’s the highest compliment you can pay to a player and is generally reserved for only the most complete athletes, like Ken Griffey Jr. and Willie Mays. In fact, Major League Baseball estimates there are only 8 five-tool players in the game today.

Everyone looks for slightly different things in the designers they hire, but for me, there are five tools that stand above the rest.

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Books to Expand Your Perspective

Over the course of the last year since leaving Twitter to take some time off, I’ve managed to catch up on a ton of reading. Real reading. Actual books!

I don’t think I’ve read more than a few books a year since I was a kid, but in the last 12 months, I’ve managed to keep a healthy pace of 2 or 3 per month. Two books have stood above the rest in terms of expanding my understanding and perspective of how the world works:

  1. A People’s History of the United States by Howard Zinn.

    One of the birthrights of growing up in the United States is that you are indoctrinated at a young age with a very rosy version of America’s history: the journey of a group of people seeking freedom, discovering territory, declaring independence, drafting a benevolent Constitution, and then over the course of the next few hundred years, building America into what it is today.

    While a lot of it is true, it is written from the perspective of “the victors” (as most history is). This book takes the opposite approach, instead opting to tell the story of our country through the lens of those who’ve been taken advantage of (i.e. Native Americans, women, slaves, immigrants, minorities, the poor, and even what we think of as “the middle class”). The author admits that just as textbooks are biased in one direction, his book is likely biased in the opposite direction, but the point is to better balance our view of how America began, what our behavior has been like throughout the course of our history, and what power dynamics continue to shape our society.

    I might go so far as to say this is the most important book I’ve ever read. If we are going to get through the next few years and beyond, it’s important that everyone have a sober perspective on how we got here, and the tensions that have been around from the very beginning.

  2. Guns, Germs, and Steel by Jared Diamond

    Speaking of “how we got here”, this book rewinds the clock even further, explaining how modern humans evolved from Homo Erectus to a (mostly) intelligent species spanning every continent on earth. The emphasis is less on physiological evolution and more on the sociological advances that enabled us to live as we do today.

    There is a good amount of material on agriculture, the invention most responsible for our modern way of living, but there are also fascinating storylines about why certain groups of people ended up where they did (e.g. Africans in Africa, Europeans in Europe, etc).

    If you want to get caught up on the story of humans in a single book, this is the one to read.

What’s Next

Jason Kottke had an interesting post which linked to two reading lists from a guy named Cass Sunstein, who worked under Obama and seems like a pretty well-rounded political scholar. The first list is 5 Books To Change Conservatives’ Minds, and the second list is 5 Books To Change Liberals’ Minds.

I am going to try and read all ten, and I won’t lie: I’m not exactly looking forward to it. 176 pages from Antonin Scalia isn’t the sort of thing that gets me up in the morning. But I guess that’s the point!

To make things easier, I’m going to tackle this in machete order. Left, right, left, right, until they are all vanquished. If you’d like to do the same, I sorted them into two public lists — left and right — ordered by number of reviews. Might as well read the popular ones first.

Will report back when I’m done. Happy reading, people!

(This post also available on Medium.)

Behavioral Targeting is Getting Scary

This fascinating article about how an “election management firm” — under contract with the GOP — mined social network data and used it to bombard impressionable voters with content designed to manipulate them is thought-provoking and troubling.

Go ahead, read it first, and then come back. Also, for balance, read this counterpoint from Bloomberg doubting the data’s effect on the election, and listen to this podcast from Michal Kosinski who is the Stanford researcher featured in the article. Kosinski is unsure what effect data mining and targeting had on the election, but has plenty of fascinating things to say.

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“Is This Helpful?”

The first book I checked off my list this year was one I had heard about thousands of times since I was little but never actually read: 1984 by George Orwell.

I think what finally got me over the edge was this Reading List for the Resistance from Jason Kottke, so thanks Jason.

I very much enjoyed the book, and in a way, I’m glad that I waited until this very instant to read it. I think my younger self would have dismissed it as delusional and irrelevant, as I tend to retreat from science fiction the moment it feels implausible to me.

Reading the 1949 novel now though, at a moment in which the stiff boot of authoritarianism threatens to become part of American lives for the first time, I’m struck by how prescient it now seems.

There are a lot ideas from the book that feel more and more familiar in today’s world, but the one I can’t get away from is the concept of newspeak. For those who haven’t read the book, newspeak is a new language developed by the oppressive government that drastically reduces the amount and complexity of words in order to drastically reduce the amount and complexity of thought amongst the citizenry. The idea is, if you can remove say, 95% of words from the English language, new generations will not be able to formulate the undesirable thoughts represented by the eliminated words (think “coup”, “resistance”, “steal”, etc).

The end result is something of a pidgin. Very basic sentences, using a tiny subset of words, representing the minimal amount of thought necessary to keep the wheels of the totalitarian society running.

It strikes me that many of our communication channels today — while not being created with any sort of negative intent — may have ended up with similar properties:

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Shipping vs. Learning

“What did you ship last quarter?”

“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?

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All Olympic Logos, Ordered By Quality

AIGA just published a fantastic rundown of all Olympic logos, as graded by Milton Glaser. Glaser is a legend, having created some of the most iconic design work of the 20th century, including the I ❤️ NY logo and the fantastic poster for Bob Dylan’s Greatest Hits.

Logos, however, are a subjective endeavor, and one man’s trash is another man’s treasure. In other words, there is little objective truth in logo design… only a preponderance of opinions and feelings. It is possible to objectively grade a logo’s craftsmanship by looking for transgressions in things like alignment and stroke width, but in terms of how a mark makes you feel, beauty is much more personal.

With that in mind, there were some things in Glaser’s grading that I agree with and some that I disagree (even strongly) with, and thus, I decided to re-rank them according to a few criteria:

  • Craftsmanship: How well is the logo made. You’d think more modern marks would have the advantage here, given how design tools have advanced, but that turns out to not always be the case.
  • Timelessness: Newer marks have obviously experienced less patina throughout the years, but I try to correct for this in the grading. One could argue that for an ephemeral event like the Olympics, timelessness doesn’t matter, but as designers we should always aim for it when we can.
  • Typography: Type in general is not strong across most of these marks. There are some notable exceptions though.
  • Overall impression: This is the most important part of the grade as it is the true indicator of a logo’s effectiveness. It is also, however, the most subjective.

With those criteria in mind, here is my re-ranked list, in order of worst to best. Since I’ve ordered it this way, instead of by year, there is also a lot more snark at the beginning, but bear with me. Additionally, it’s important to remember that in practice, logos often go through many layers of politicking, compromising, and otherwise watering-down of what may have once been something much more impressive. Sometimes it is the designer’s fault that something didn’t turn out great and sometimes it is external factors entirely.

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Evaluating Employees in Product Design & Development Roles

Results. Metrics. Impact.

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.

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Three Years in San Francisco

I had only been to San Francisco on random business trips and a couple of times with my family when I was very young. It seemed like a place I might live if I had never found Seattle.

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.”

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Reboot!

It’s been 7 years since I last redesigned Mike Industries, and it feels like even longer. The old design still holds up considering the largely desktop audience it was designed for, but since it’s May 1st Reboot Day, and I’ve had some time on my hands since leaving Twitter, I thought I’d release a shiny new version today.

Say hello to Mike Industries, Version 3.

What is wrong with the old Version 2, you ask? Well:

  • It’s not responsive.
  • It ingests and displays all of my Tweets and saved Tumblr links, which seems like overkill now.
  • Because of all the peripheral stuff being displayed, WordPress isn’t able to assemble the page very quickly and browsers are also slow to render it.
  • It doesn’t take advantage of any of the great HTML, CSS, and related advancements that have developed in the last few years.
  • It was just time for a change, and I felt like getting back into pixels and code again.

While I’ve spent the last few months putting this together, it only occupied a day or two of time per week. Lots of fits and starts, including periods of frustration and reflection where I’ve asked myself “Why am I not just moving everything to Medium?”

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