My introduction to Scott Berkun was his amazing talk at Webstock 2008 on the Myths of Innovation, based on one of the three books he’s published in the last decade. I remember his talk not only because of the compelling content, but because he eschewed the traditional get-to-know-you slides in his presentation – he jumped right in.

His latest book, Mindfire, is a self-published collection of best essays from his invaluable weblog.

RANDS: After many years out of the game, you recently started working at Automattic. Why the return to industry? Was this always the plan?

BERKUN: I have always hated arrogant author/consultant types who had either never done the job themselves, or hadn’t in decades (See How to Call BS on a guru). After writing 3 books and being a speaker for hire for a decade, I was becoming that guy and I knew eventually I should get back into the fold and see how much of the advice I give people I practise myself. The opposite of a sabbatical. The awesome Matt Mullenweg approached me about Automattic, and as I used WordPress for my blog, it seemed a great way to return to the front lines for a time. Since 2010 I’ve managed a team of designers and developers working on WordPress.com.

After being out of the game for a decade, what changes (if any) did you notice with the software development teams?

The important things are the same: do we trust each other? Are we motivated? Are there clear goals? Can we move roadblocks out of our way? As simple as those four things sound, they’re rare. Always have been and always will be. As a leader, my job is to make good decisions, and if I do that, all four of those things become true. I did notice some superficial things that have definitely changed: namely that I’m old. My jokes and references get blank stares. But that’s recoverable. If you watch enough YouTube videos to catch up on the references du jour, you do fine.

Your most recent book, Mindfire, is self-published. What was the reasoning behind this decision? And what were the most valuable lessons learned?

The best way to learn is to do. I’m going to be writing books as long as I’m alive and I need to learn all I can. Doing something yourself forces you to learn every angle. Even if I never self-publish again, the way I can talk to any publisher is different: I know more. The big lesson is that self-publishing is easy. The technology is amazing. Anyone can easily publish a book for not much money. There are no excuses. The real challenge is, as it always has been, writing a good book.

How has the conversation with your publisher changed?

It hasn’t changed much, which is nice. O’Reilly Media has been very cool. Joe Wikert, General Manager at O’Reilly, interviewed me in a video cast, where we had a frank chat about all the related issues. Why I did it. What I learned. What I’d recommend to authors and publishers. How cool is that? He even helped plug Mindfire.

The book is a collection of essays from your blog. How did you go about picking the articles to turn into chapters?

Every 4th or 5th post on the blog has asked big philosophical questions in a fun way. Book smarts vs. Street smarts, Hating vs. Loving, or How to detect BS. I wanted to take all those posts that asked big and fun questions and fit them into a single volume focused on that kind of thinking. We made a long list of candidates, and then removed ones that didn’t fit together or had no easy place in the flow of essays.

Your title at Microsoft was program manager. I think there is a lot of confusion about this role — what’s your best definition?

It’s a glorified term for a project leader or team lead, the person on every squad of developers who makes the tough decisions, pushes hard for progress, and does anything they can to help the team move forward. At its peak in the 80s and 90s, this was a respected role of smart, hard driving and dedicated leaders who knew how to make things happen. As the company grew, there became too many of them and they’re often (but not always) seen now as annoying and bureaucratic. In simple terms they are team leaders; good, trusted sergeants near the front lines.

Do you think there is a cautionary tale in the rise of power of the project/program manager relative to Microsoft? How might you prevent that in other companies?

The short answer is too many cooks. The long answer is, in the case of Microsoft and most successful companies, decay and bloat are inevitable. The story of PMs at MSFT is just part of that. You can’t be lean and have 100,000 employees at the same time. Some roles don’t increase in value as you add people, particularly meta-roles (e.g, leads, managers, etc.) Somewhere along the way the ratio of PMs to engineers got out of control, and as soon as PM types were in charge of controlling that ratio, it’s not a surprise no corrections were made. Over a few years it becomes part of the culture, and all the developers expect PMs to be there to protect them or do the annoying work. It becomes symbiotic. In some cases, it’s codependent, but not always. The basic rule I was taught, which has been forgotten, is make the tough choices. If you can’t make decisive choices, you’re lost. I bet if we asked most PMs at Microsoft (or managers at any large company) if there are too many PMs, they’d passionately agree. The problem and the solution is all right there.

At what point/time/team size/inflection point do you think a team needs a program manager?

Once you have more than a handful of developers, leadership activities emerge naturally or productivity drops. Who is the tiebreaker in tough arguments? Who figures out how everyone’s work will fit together best for users? Who makes the best trade-offs among time, resources, and customers? Who has the clearest vision and articulates it the best? Who knows how to say NO? A program manager is an encapsulation of many of those intangible leadership and decision-making skills into one person.

According to Wikipedia, you have a goal to fill a shelf with books that you’ve written. First, what is the origin of this story? Also, how many books does it take to fill a shelf?

When I quit to try and be a writer, I needed a visible goal. Something I’d see all the time. A book is hard work, but in the grand scheme it’s nothing: I want to die with a body of work, and having a long-term goal makes many short-term choices easier to make. I cleared the shelf closest to my desk and the only thing I’m allowed to put on it are books I’ve written (4). I haven’t measured it as it’s mostly empty, but I suspect I need to write 25 books to fill it. I believe I’m entirely capable of this challenge; it’s purely a matter of priorities and I hope the empty shelf helps me prioritize my working life.

I’m always curious about a writer’s process. Can you walk me through the process of how an idea turns into an article?

As a fun cheat answer, I made a time lapsed video of this process, with audio commentary. It’s all there.

What is your perfect writing environment?

I’m not that picky – with the right music I can concentrate anywhere. I work mostly in my home office, but I can write in a coffee shop, too. If I’m working on a book I need more desk surface area for notepads, books and things.

What’s the next book?

All I can say is it’s something different 🙂