Like a Boss

(This is not the blog post I meant to write, but I kinda got into it! Fun!)

Eventually, I might want or need to be a boss.

I don't think this is a natural role for me, and I think in general it's fairly hard to do well. I've been impressed with my current boss (good thing this blog is anonymous), so I wanted to take some notes. If I ever do become a boss, I'll probably do a couple interviews with good bosses to find out more.

So, here's my current simplistic model of how to be a boss (in fields like mine, where people aren't necessarily filling pre-defined roles):

0. Hire people you feel really good about; a good rule of thumb might be being confident that they'll be great at at least one mission-relevant thing.

1. Ask the person to do something that is mission-relevant and that they're good at. You probably hired them for their ability at some task, or with a suspicion that they'd be good at something; start them there. If you didn't hire them, maybe ask the person who did. If you strike out here, move to step 2.

My most likely mistakes on this step:

• Trying to get this person to do whatever is most mission-critical, regardless of whether they're good at it.
• Not asking them to do anything because what they're good at doesn't seem mission-critical enough.
• Not wanting to give people tasks because I think I'd be better at them. (This is a mistake because you have to push through this in order to get gains from having employees.)
• Asking a person what they want to do; this just pushes the boss' job onto them.

2. Figure out what (else) they're good at, among mission-relevant things, and ask them to do those things. Most people are good at a variety of things, and some of those will be mission-relevant. Ways to do this:

• Ask them what they think they were best at at their previous job.
• If they had a good boss or good co-workers at their last job, ask those people what they were best at.
• Guess what they might be good at, and ask them "How would you feel about doing x? I'm wondering if you'd be good at general class of things X, and this would be a good way to get some information about it."
• Ask them if they've seen anyone else at your org doing a kind of task they think they'd be good at. This is a little risky, since it kind of pushes the boss' job onto them.

My most likely mistakes on this step: again, probably being too exacting about what is mission-relevant.

There are some other things that seem good, but less critical, to me:

• Gauge autonomy; different people need different kinds and amounts of guidance.
• Give performance feedback.
• Actually care about their life, and show it.
• Get data about how their work is going, and demonstrate that you won't abuse that data (and that you'll use it to help them). I suspect "what an employee is doing" is very mysterious, and any data you can get will help, but giving data (like a timesheet of what they did and how long it took) is a vulnerable place for an employee, so you have to acknowledge their fears of being judged and demonstrate that you won't abuse this privilege.

Overall, the thing that a boss seems to need to do, in addition to being cool to people, is hold a picture in their head of what tasks are mission-relevant and what capabilities employees have, and then pair people with tasks in a sensible way. I'm sure there's a lot more to it, but I didn't have this basic model before, so it feels like progress to me.