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A Two Year Old Conversation Shows Up In a Book

I asked a question. I got a hammer.

Scott Berkun published a book this week called The Year Without Pants. It’s about working at, where Scott and I worked together.

Don’t believe the hype. I regularly wore pants.

I haven’t read Scott’s book, so this isn’t a critique of anything besides the three sentences I’m about to mention.

A couple former colleagues told me that I was mentioned in the book, which was the first I’d heard of it. I didn’t know the context until last night when I saw a screenshot of this excerpt:

In several frustrating debates, Evan Solomon, a programmer at the company, would leave a first comment that asked big questions. The questions were good ones, but for my purposes, the timing was frustrating. They sent the thread in a very different and, for me, useless direction.

It felt…weird to read that section.

I joined Automattic (the company that makes in March 2011, about one year after Scott. He was one of the very first people I met, which was a relatively infrequent occurrence since we were a distributed company. I knew he had been a writer, but I had no idea he was writing a book about Automattic. He was just a normal employee, what would be a product manager at most other software companies. Scott left Automattic in mid-2012, about a little over a year after I joined, and by that time he had announced that he was writing a book.

I never thought of Scott as anything other than a colleague. He wasn’t there as a writer or journalist, and he wasn’t doing research on Automattic, he was just a guy running one of our product teams. It would probably be foolish to call work a private place, but it’s certainly not a public one. In general, I don’t consider the way things I do at work would play in a book, and I believe that’s for the best.

Scott and I clashed plenty of times. I wouldn’t call our relationship combative, but I wouldn’t call it calm. We disagreed about plenty. I like to debate things that I care about when I disagree with someone, so we did.

I’m not sure how to interpret Scott’s portrayal that I sent conversations in “useless directions.” I’m sure I have done that, but not intentionally. Even if it was intentional, was it so common that I deserved to make an appearance in a book as the programmer with a “big question” chip on his shoulder? I mean, maybe? Who knows? How the hell do you decide what sort of interactions you should expect to end up in the book about your time at work?

It’s a weird thing to read.

The most frustrating discussion I ever had with Scott ended up being about a hammer, for reasons that still aren’t clear to me. He had written a post about a product development technique he’d used with his team during a meetup in Hawaii.

Brief aside: I don’t remember the name or details of the technique. If any current Automattic employees want to dig up the thread, I’m pretty sure that “evansolomon” and “hammer” would make a high cardinality search query.

So Scott wrote this post, which I think was about a method for storyboarding user problems and fitting solutions to them, and suggested it as a thing other teams should try. To be honest, the idea seemed interesting, but it was a pretty detailed and confusing process that I didn’t understand well. In particular, it was hard for me to figure out why it was better than any alternative.

I tend to learn best by doing, but in this case I tried to take a short cut and ask Scott what kind of products are good examples of this kind of problem-design-solution fit. In other words: when this process works, what gets created and why?

To this day, I still can’t tell you how or why that conversation came off the rails. We probably had a dozen replies back and forth, me trying to get an example of what success looked like and Scott wishing I hadn’t gotten out of bed that day. It was super frustrating. I was trying to understand the way to use this process he was trying to teach people about, but for whatever reason I wasn’t getting through to him in the way I hoped.

Eventually he sort of relented when I asked for the third or fourth time what an example of a successful outcome of this process might be. In hindsight, it’s probably as pure an example of my “big questions” that led to a “useless direction,” which became clear when he gave me an answer.

A hammer.

What the fuck? I didn’t even know what that meant. You think we should use a process that at its best will produce a hammer?

We were talking about a design process in the context of a software company, and the example of it working was a physical tool invented thousands of years ago? Don’t get me wrong, I like hammers just fine and get the argument that they’re well designed. I just wasn’t sure what Scott thought I’d learn from that answer.

Oh, thanks. Totally makes sense that if we use this process we can make something as great as a hammer. Have an A1 day!

— Me, never

The hammer remains a confusing-but-funny memory. Scott told me directly at the time that he was frustrated with the way my questions had influenced the conversation. I told him that I was frustrated by his refusal to explain the parts of the post that I didn’t understand. Like a couple staying together for the kids, we implicitly agreed to remain mutually frustrated.

I understand that it’s frustrating when you try to communicate one idea and the conversation goes in another direction.

It turns out to also be frustrating when a conversation from two years ago is recalled in a book you didn’t know was being written at the time, and you become the “programmer at the company” who derails conversations in useless directions. I’m not sure whether it would have changed anything I said, but it certainly never crossed my mind when I was trading comments on that thread with Scott that they’d ever be seen outside of Automattic, to say nothing of available on Amazon for $16 in hard cover.

I still try to ask big questions. I try even harder to be receptive about answering them when they’re asked of me.

Asking questions is the way I learn things, and I hope it’s also the way better ideas get formed. In many cases I think those are valuable outcomes, even for the person that started the conversation. When that’s not true, I guess I just have to think harder about whether that person might be working on a book deal.

I’ve never been written about in a book , so it caught me off guard for the first time to be a in pretty negative light. I worked in PR for a couple years and had my fair share of experience dealing with negative press, but those situations came from interactions under a specific pretense. Talking to a reporter is a lot different than talking to a colleague — expectation of privacy, in particular, is a lot different.

I never worked directly with Scott, so I had no idea whether I would be in the book. I haven’t talked with Scott in over a year and hadn’t thought a lot about it. If forced to guess would have predicted that I wouldn’t be in the book.

I don’t know what the etiquette for disclosure or even permission is like for cases like this. On one hand, it’s weird. On the other hand, it’s kind of unavoidable.

Companies are dysfunctional, complicated, idiosyncratic things. I believe that it’s impossible to honestly write about one and not offend at least some people, so it’s hard to blame Scott for doing that. Again, I’m not sure when the idea for a book was explained to everyone at Automattic, though Scott explains that the founder and the CEO knew from the beginning.

When Matt Mullenweg (WordPress and Automattic Inc. founder) and Toni Schneider (Automattic Inc. CEO) offered me the job, I told them I’d do it only if I could write a book about my experience and they agreed.

I think that’s a mistake. It puts employees in a difficult and ultimately lose-lose situation to be unsure whether conversations are private or public. It doesn’t bother me much that Scott was frustrated by my communication style, but I don’t think it’s his place to share that frustration with the world any more than it would be my place to talk about my current colleagues’ personal habits at work without their permission. I would consider doing that a clear violation of trust.

What if one day I want to work at a company, but the founder read Scott’s book and remembers me as that “useless direction” guy? Likely? Probably not. But not impossible, and a pretty bad result for me, for Automattic, and probably for Scott.

Would it have been better for me to just shut up and watch a predictable conversation unfold that praised Scott’s post about an interesting way to design software? Well, maybe. I would have avoided this somewhat silly characterization in his book, but I also would have been frustrated to see a conversation that wasn’t appropriately critical.

In hindsight, I don’t think I would have changed my response, but that might not be true of most people. One thing I’m left really sure of is that implicitly forcing employees to manage this balance is going to end poorly for at least some of the people and organizations involved.

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