Learning What Not To Do Doesn’t Teach You All That Much

Early on in my career, I worked on something that shipped without tests. And I learned something important:

That’s a bad idea.

To frame it positively, I learned that any tests were better than no tests. And so I went away and read things, talked to people, and experimented. And over time I’ve learned a lot and mastered a certain level of competence. I’ve also become the kind of person who writes extensive unit tests on my experimental side projects.

But it’s not uncommon for people in tech to claim they learned their leadership skills, or management skills, from learning what not to do from some terrible leaders and – especially – managers.

There are a number of things wrong with this. Firstly, these create self-perpetuating cycles. We’ve all heard (and often told!) stories of terrible micro-managers, I heard about one who had his team track their time in 30 minute increments (just the thought of this makes me stressed). The result is that many of us fear being the micro-manager, and so we tend to be too hands-off.

The thing is, if you could get past your loathing of the micro-manager and actually listen to what they think they are doing, you might hear a story about how they had a hands-off manager, and didn’t get the support they wanted, so now they are trying… not to be that guy.

So we’re all trying to… not be that guy (I use “guy” deliberately, because the vast majority of the time it is a guy). Cool. I totally believe that guy was a terrible manager, or terrible lead. But that doesn’t mean that we know what the hell we are doing.

So we read things (but mostly ignore all the wider research outside the tech industry), we talk to people (do we know that they know what they are doing? Did they make it up from some other place of things not to do?) and experiment.

Only now our experiments are not with source code. But with people’s careers. In an industry where people’s careers make up an unhealthy level of defining who they are.

I’ve learned a lot of what not to do. But recently I learned something about what to do. Specifically, if you lead through a hard thing, especially something that fails, the best measure of success you have is the relationship you have with the people you led. If you get through it and they still respect and like you, you’ve done something right.

And it made me realise how little we learn when we learn what not to do. And how many unknown unknowns it leaves us with, that will one day come back to bite us.

The other thing I’ve observed recently, is that the way someone treats a new grad, or an intern, says a lot about them. It’s like that tip of seeing how your date treats the waiter.

Yes, some interns and new grads are arrogant and obnoxious. But in general these are the most enthusiastic and positive people you meet. You are amongst their first experience of what people are like in the working world. They are so keen to like the people they work with, and they are the people who we conduct the most brutal experiments of poor management and poor leadership on.

And so, they learn what not to do. They learn not to be that guy, only now that guy is you. And the cycle continues.