critique your boss (like you’re politically naive)
That’s the advice. I had a few other more nuanced and careful ways I was going to title this one. But I scrapped those. This is what I actually recommend. A premise, some rationale, and context:
Premise: You see something your boss could be doing differently or better. Maybe this is an individual tic of theirs that shows up small scale, in informal meetings; maybe it’s a decision or pattern that impacts the culture or strategy of the whole team. Either way, I tend to see three approaches to this fact pattern:
You tell your boss. Give them the feedback.
You talk to a peer about it. (When I’m feeling my oats, I just call this “gossip”).
You stifle it. Let it go.
Rationale & Context: The politically shrewd reader gravitates toward options 2 and 3, likely with a preference for 3, unless they’re doing something real Machiavellian like trying to get their boss canned or demoted or something. The boss is the boss - they have power over you. Why would you affirmatively choose to do something that could tick them off or make you look arrogant?
Feedback that is good (ie useful) and good-hearted (ie generous to the recipient) can get scarcer and scarcer as you move up in an organization. Your job becomes more and more about helping other people (and teams) to do their jobs better, through the provision of clarity, capital, or feedback. Those same people rarely see their jobs as helping you get better at yours. At the same time, you have fewer people above you who do see their jobs that way. Those few people, it turns out, are likely among the busiest at the organization and they (hopefully, correctly) assume you’ve gotten where you are because you can figure things out and author your own improvements. Your growth might not be their priority.
Your boss might be in this exact pickle. If they are, your feedback - the thing you noticed and had the guts and care to bring to their attention - can be the best sign that a) you take the right things seriously (you get it) and b) you have their back.
If it helps you find the nerve, couch your feedback with any disclaimers you wish. Just don’t attribute your feedback to anyone else (that is not politically naive, it’s politically stupid: you sound like a gossip and you lose credit for the feedback that was yours in the first place).
-eric
