Why I wasn't cut out for management

Perhaps the most important ingredient in my career's success is my seemingly infinite capacity for self-criticism.

I constantly inspect my work, effortlessly identify ways it could be better, and never tire of making improvements. And because the time it takes to finish a task can always be improved, this tendency rarely veers into unproductive perfectionism. On the rare occasion I feel like I really nail something, I strive to nail it even faster next time. At the same time (and as anyone who listens to Breaking Change knows), I have a very healthy ego. I genuinely believe I am good enough, despite simultaneously knowing my work never is.

The trouble is, while this disposition might be dynamite for self-improvement, it doesn't gracefully scale to teams and organizations.

I'm thinking about this because yours truly was a dummy again and found the Hacker News comment thread for one of my posts and chose to engage:

I've been griping about LLM overconfidence for years, as somebody who is racked with self-doubt and second-guessing. On the one hand, my own low opinion of myself made me a terrible mentor and manager, because having a similarly zero-trust policy towards my colleagues' work caused no end of friction (especially as a founder where people looked up to me for validation). On the other hand, I don't know very many top-tier practitioners that don't exhibit significantly more self-doubt than an off-the-shelf LLM.

I'm not sure I've ever explained this publicly before, but this predilection for doubting myself is fundamentally why I was never a particularly good "senior" member of a team. As Test Double grew, we managed to create spots where I could remain a practitioner, but we also had to be mindful of limiting the blast radius of my reflexive hypercriticality. The truth is that my special sauce depends on constant emotionally vulnerable self-critique, and that made it extraordinarily difficult to manage or coach people directly. Even for people who are wired similarly to me—which many of Test Double's agents are—it's one thing to look at your own work and spot endless opportunities for improvement, but it's quite another for someone in a position of authority to do the same.

Every time I was charged with evaluating someone else's work, it started up the same engine that generate an infinite supply of shortcomings in my own. And it wasn't that I was incapable of prioritizing or rate-limiting my comments—it's that when people came to me with revisions, I'd always find fault in those too—because I can always find ways the work could be better! It led to people feeling like they could never be good enough for me.

After touching the hot stove once or twice, I learned to spend all my time assembling shit sandwiches to protect people's feelings, or my relationship with them, or—as a highly visible co-founder—the company's reputation. Every patty of pointed and meaningful critique demanded two slices of ego-insulating bread. And one man can only bullshit his way through so much halfhearted positive reinforcement and self-effacing humility. Even if I hadn't found all that tap-dancing to be a nerve-wracking waste of time, everyone could see through me. It wasn't authentic.

Are there ways I could have overcome all this and become a good manager anyway? Probably. But would I risk losing the thing that made me unique in the process? Possibly.

I'm writing this in part because it's so clear that LLMs-as-products are being sold to us with the default wiring of a capital-B Business Guy, and their shortcomings resemble the same shortcomings I see in humans who are insufficiently self-critical. But it's also possible you, reading this, are a Business Guy and you're curious how so many amazing programmers turn out to be shit at coaching less-skilled colleagues, the root cause may not be poor communication skills: it may be that the self-criticism that drives some practitioners to greatness is impossible to convey safely to others without risking a call to HR.

Anyway, if you identify with me, but have nevertheless made the transition to manager and leader gracefully, then I applaud you. (I'd also be curious to speak with a couple folks who report to you and see what they have to say.)