From trying to impress engineers to trying to impress managers

In the first few years of my career, I knew next to nothing about how to do good work in a tech company. The senior and staff engineers I worked with seemed like magicians: they effortlessly solved problems that I couldn’t even understand. While I was learning how to save something to a database, they were struggling with scaling and design work on which the entire company depended. I wanted nothing more than to do the kind of work that would impress those engineers.

Now I am a staff engineer. I effortlessly solve problems that brand-new engineers struggle to understand¹. I am involved with high-stakes scaling and design work: not quite at “save the entire company” level, but certainly hundreds of millions of dollars of annual revenue are in the balance. I’m happy with where I am in my career. But climbing the ladder changes who you have to impress, and that can be a difficult transition to navigate.

Progressing in your career means impressing people you may not respect

Before I became a software engineer, I wrote poetry. I started writing poetry because I was blown away by the poetry I read: by Kipling and Coleridge as a young child, and by Milton and Auden as an adult. I aspired to write the kind of poetry they might have been impressed by. However, if you want to have your poetry published, you cannot write like Milton and Auden. You have to write the kind of poetry that gets published in magazines and journals. In other words, you have to stop trying to impress the ghosts of dead poets and start trying to impress the kind of people who edit poetry magazines.

I got a handful of poems published this way. But I was never much good at it, and the whole thing left a bad taste in my mouth. I have nothing against the people who edit poetry magazines. Still, I certainly don’t respect them in the same way that I respect Milton, and trying to do creative work in order to impress people you don’t respect is corrosive to the human soul.

The dangers of impressing product managers

Something like this happens to many software engineers as they transition from junior to senior. You can get promoted from junior to mid-level by impressing the senior engineers on your team, since your manager typically relies on them for a sense of how you’re progressing. However, getting promoted to senior or staff (or beyond) requires impressing an entirely different set of people: managers, product managers, directors, VPs, and even C-staff.

If you were a junior engineer motivated by impressing senior colleagues, changing the way you work to impress executive and product folks may be a rough transition. Those people are powerful in the organization, but they don’t visibly solve hard technical problems in the way senior engineers do.

Engineers are impressed by different kinds of work to managers and product managers. I’m most impressed by an engineer who runs down a very difficult bug, or some kind of weird operational issue that was hard to debug. In my experience, managers and product managers are impressed by speed: being able to fix an issue rapidly, or to deliver some piece of UI ahead of schedule. Both speed and debugging require technical ability. But if you’ve optimized for the first, you’re going to have a bad time if you expect your product manager to be amazed by your technical investigation.

Despite that, managers and product managers are also easier to impress. What I mean by that is that they’ll typically give lots of positive feedback to engineers who are good at getting things done. In fact, they’ll give more positive feedback than you’d usually get from a senior engineer, who is likely to temper their feedback with concrete technical things you could have done better. This makes it relatively smooth to transition from “impressing your very strong engineering colleague” to “impressing your friendly product manager”: by focusing on work that your product manager values, you’ll get both immediate positive feedback and longer-term career value.

However, the positive feedback you get from impressing product managers is “empty calories”. It feels good to get kudos and to grow your career, but it won’t satisfy the desire to have a competent colleague value your work. Even quite technical product managers are not engineers. They don’t have an accurate sense of what’s impressive or unimpressive from an engineering standpoint - that’s what they’re relying on you for! Many things that are trivial to implement are highly valuable from a product perspective, and vice versa, but the feedback you get will only track product value.

Impressing engineers lasts much longer. In my experience, managers and product managers are more professional: they’ll be very friendly while you’re working together, but once you stop being useful they immediately lose interest². This can be disheartening for a mid-level engineer who thought they’d been building a durable reputation. But it’s just the way it is - you’re doing different jobs, and since they don’t deeply understand what you did, they don’t really have a personal interest in it³.

What if you don’t want to impress anyone else?

There are three broad ways I’ve seen engineers deal with this problem.

The first is to throw yourself into impressing managers and product managers, and just deal with the fact that you’re not being validated for your work in the way that’s most emotionally satisfying to you. I don’t recommend this. It seems to me like a pretty rapid path to burnout.

The second is to opt out: to decide that if you need to impress non-engineers to grow in your career, then you’re perfectly happy staying where you are. Many “greybeard” engineer types fit this pattern. Every company has engineers who make their own technical decisions without much regard for the project-of-the-hour, or for their own career progression. I have a lot of respect for engineers who do this - so long as they’re happy to accept the consequences.

The third way is to try and find satisfaction without impressing other people: optimistically, in shipping concrete things that have value to users; cynically, in amassing wealth and organizational power. Wealth, power, and impact are intrinsically pretty satisfying! This is what I’ve done, broadly speaking, and it’s working well so far.⁴

Final thoughts

Not all engineers are motivated by impressing their peers. People are complicated and motivated by lots of different things. If none of this speaks to you, that’s fine. But I was definitely wired that way. I wanted to write about how being promoted requires impressing different people, and what that experience is like.

I’m pretty happy with how I approach my work now. I’ve certainly written enough about it on this blog. That said, I do sometimes miss the time when I was just throwing myself into it, trying to do work that my more senior peers would be impressed by.