The imposter director revisits the cradle
LifeIt isn't something I really emphasize on my résumé or in interviews, but for a spell (more than a year? Less than two?) I was Puppet's engineering director for the platform team — the people who made the core open source Puppet distribution.
I was assigned the group in the wake of a re-org that had made a ton of theoretical sense for the many teams working on everything but the platform, but had made no sense for the platform team itself. I wouldn't have ended up with that group, but there was a lot of disaffection over the re-org, a manager in the group was struggling, and some key players had departed. It was a damage control assignment, but I was excited to take it because after five years at Puppet, where I'd started as the embedded tech writer on that team, I got to come back and lead it.
This was one of the few director engagements I've ever done where skip-levels were just a necessity. Not a "keep up with the temperature" thing, but a "I don't care about the team manager's boundaries, she's losing this team" must-have.
My actual contributions were not the kinds of things real engineering leaders would consider résumé highlights:
As soon as I had an opportunity, I de-reorged them. We used a breakout session at an SKO to workshop how they were supposed to be organized, and we did that. It took a minor amount of arm-twisting and an imprecation to please not advertise the whole thing, and during our workshop my boss was standing in the back of the room with his arms folded, but after the session he said "I can tell it worked."
I mediated one slap fight with a senior technical stakeholder over whether to make something in a language none of them were proficient in on ten weeks' notice, or in a language they'd already done half the work in.
And I invented a conception of product ownership and team leadership that kept the group aligned with the wider organizational changes in a way that was organic to them and how they worked. The thing I love most about that is that the change stuck after I moved on from that team, and I can still open LinkedIn every now and then and see people at Puppet who moved into product management roles from engineering roles who got their start from that innovation.
I felt a weight during that time, though.
I wasn't a very experienced director. I wasn't a software engineer. In the "what/how" parlance of describing performance, most of what I could bring in the way of leadership for that group was "how." My boss's take was "your common sense is better than most, so keep listening to it." I wasn't telling that team anything about their what, and I think we were all clear on that: Most of that team remembered when I had been their embedded tech writer a few years ago, and possibly the time I volunteered to "leak" on Twitter that we were considering moving part of our stack into a jvm so they could all say the hapless tech writer misunderstood a conversation if the community backlash was too strong.
Eventually that weight became too much. I'd been approached a few times from people around the business who knew me by reputation and wanted to recruit me. Each time I'd have the conversation, then decline because I might not have been anybody's idea of a normal engineering director, but I incurred an obligation to see that team back to health.
My boss got a new boss, and it came back to me that during review season I took a hit in a calibration session because "Mike's how is too good for his own good. He gets to skate on the what." Which ... fair. Add in some nervous fretting on staff that the boss's boss had been poring over GitHub activity graphs looking for "the 10x guys," and I had the distinct feeling that I wasn't going to do well in the new regime. It finally made sense, when the opportunity arose, to step aside and move on to another role.
There's always an urge to wrap anecdotes in some sort of just-so story or moral. There's not really a moral to the story, because the fact is that the closest "10x guy" to the problems I needed to solve when I was asked to go lead that team wasn't solving them and could not solve them. They needed a "how" person, I did "how" stuff, and eventually the circumstances and connections that had allowed that to work stopped being material. That's business. You can either choose to submit to a constant process of "seeking alignment," or you be you until that doesn't work for someone whose opinion matters.
Anyhow, that's all on my mind because last night I went to a small Puppet reunion and a bunch of folks from that engineering group were there. Some of them still hanging in at what's left, some long since moved on. People I remembered sitting around a table with as the tech writer during a platform group retro in 2012, people I remembered sitting with in 1:1s as the group's director.
I remembered one in particular because he drove me to get better at directing in a hard way, by finally making me say, "I don't like what's going on either, I've done what I can to blunt the impact, I think things are better, but I can tell it's not enough for you. All I can say is that we can't put it back any more than we already have. This is where the business has taken us." It was a hard thing to say because the mandate had been to stop the flight, but it taught me one of the three or four things I believe to be very true about management, which is that people are worthy of knowing what their real choices are, whether they're going to like the choices you present or not.
And I remembered all of them because my experience at Puppet included a kind of generosity I haven't experienced many other places. Maybe I was the former-tech-writer-turned-director-due-to-unfortunate-circumstances person, but they all shared what they knew, took the time to explain problems even if it took me a while to understand, and extended trust in return that I'd go do my "how" thing on their behalf. In a place known for hiring folks with raging cases of imposter syndrome—me included—I can't imagine a better group of people to be among.
A conversational partner last night said, "it's great to see everyone here. It's a shame what's been happening at Puppet," and I said, "I'm not here because I thought hiera was awesome and I miss talking about it. 'Puppet' was these people."