As my adventures in management continue, more and more questions seem to pop into my head. Many of these questions are of the imposter syndrome variety: when are they going to figure out my incompetence? When am I going to get shitcanned? How has this thing that has happened going to piss off my boss.

It’s a lot.

But there is another question that comes up even more frequently. It seems to be perennial, a question that I always have to ask myself because it represents a constant risk in my life. That question is: how will my direct reports fuck this up for me?

I wish there were an easy way to answer this question, but the truth is that when it comes to fucking things up, human creativity truly has no bounds. Let’s look at an example.

I have the teachers observe each for the purposes of professional development, and ask them to answer four questions about what they observed. Getting them to observe the classes is pretty easy, I tell them where to be and when and they do it. That, believe it or not, was the easy part, and it only took a week longer than it should have. But then I need to get their feedback on it. I look over the email explaining this before I shoot it out, of course missing the massive grammatical error that is in my email.

I throw that in to clarify that no one is perfect. I fuck up to.

But the answers I get back truly test the limits.

Despite my outlining that I wanted it printed, signed, dated and left on my desk, at least three people but their answers into the body of an email. One person, in response to the question “who did you observe” replied with: I don’t know their name. Truly a profound and proud lack of curiosity. The overwhelming majority of people who submitted something did so without even putting their name on the document they submitted to me. That was the one that really got to me. One would imagine that putting your own name on a document would be pretty self explanatory, but it turns out that it isn’t.

But all that was slightly better than the person who didn’t seem to answer in complete sentences. Most people did the assignment in the most minimal way possible. They phoned it in with extreme indifference, and it shows.

The boss is unlikely to approve of another round of peer observations. This will annoy the teachers, but I think they earned it.