Some time back, I was fortunate enough to be promoted from engineering manager to engineering director in a large company. It was a fantastic company: great mentors, supportive structures, and devotion to the growth mindset. In spite of this, I sucked as a director. I loved the people, I liked the company culture and I believed in the products we were building, but it was a pretty miserable time of my life because I was acutely aware of my failure.

Playing the wrong game

It took me a while to figure out what went wrong. Immediately after leaving, I got stuck into a rather intense start-up, worked my ass off for several years, and didn’t really have the time or the bandwidth to think back on the history. Recently, I read something that hammered home exactly what went wrong for me and what I should have done differently. And so, although it’s too late for me now, I’m writing down these notes in the hope that some other nascent engineering director will come across this and hopefully make less of a dumpster fire of their directorship than I did of mine.

So here’s the thing: I had spent years as an engineering manager, as a founder, as a leader. And I’d been fairly successful at all of those. How hard could this be?

What got you here won’t get you there

As an engineering manager, I had focused intensely on care and growth of the people in my team. I was a devoted apostle of Richard Hackman and Etsko Schuitema. I read every growth and development book I could get my hands on. And I prided myself in my ability to get people to be the best versions of themselves. As a founder, my passion was in disruptive, innovative new products and product strategy. I’d built a number of successful products and launched them in the market. And I was devoted to the cult of lean startup and lean product management. I was equally passionate about organisation design, creating culture and putting systems in place.

Directorship was none of the above.

Welcome to the uncanny valley

This was the quote that made the penny drop:

Managers should be focused on high-performing engineering teams. VPs should be focused on strategy and the longer term. Directors are the execution machines that knit technology with business objectives.

Thank you, Charity Majors 🙇‍♂️

And that was the thing. Engineering directorship wasn’t a new, higher altitude. It wasn’t a slightly more complex version of being a team lead. It was a weird place in the middle that I’d never seen before. And in this uncanny valley almost none of the skills that I’d spent years learning would transfer directly.

So here’s the thing about that uncanny valley that’s crystal clear in hindsight: Directorship isn’t about the people directly anymore. Directorship isn’t about the craft any more. Directorship is about thinking about teams as your basic unit of work, and doing systems engineering around that. As a director, you should be thinking about your teams, how they mesh with the rest of the organisation, and how they fit into the business objectives that you need to meet in your domain. Everything else is secondary. You need to be focused intensely on that optimisation, following the org processes rather than trying to modify them, and constantly looking for opportunities for collaboration.

To be fair to myself, some of this is not just a failure of learning: I think some of this is intrinsic in my own nature. I gravitate towards coaching people, towards building products and towards product strategy. Directorship is none of these. It’s primarily about organising and building systems. So maybe it wasn’t a particularly good fit for me from the start.

How do you learn this stuff?

In that company, training and coaching were baked into the culture. When I made the transition there to being an engineering manager, I got intensive training, even though I was already fairly experienced at it. Directorship? Nada. Is it that directorship is just hard to teach, because it’s so idiosyncratic to a particular part of the business, that it’s not practical to write down a set of general criteria and principles for it. Or that when you get promoted to that level, the assumption is that you’re smart enough to figure it out (narrator: “he was not”).

Something that I wondered: Would my AI second brain have picked up the mistakes I was making and called me out about them? If I had been smart enough to ask the AI about the role and the context and how to execute well on it, I would probably have gotten good advice. Whether the AI would have managed to pick up my mistakes from all the indirect signals and context is a different question.

It’s not you, it’s me

The single thing that I learned from this whole experience is to properly check my priors. At the time, I went through many hypotheses about why I was failing - maybe I wasn’t trying hard enough, maybe it’s organisational dysfunction, maybe I’m just not smart enough/political enough/articulate enough. The one question that I didn’t ask was whether I was playing the right game at all.