I am mentoring a few people, and in one of our conversations, my mentee complained about their line manager. “He’s terrible - every time something is even slightly off track, he turns it into a crisis. We’re constantly fighting fires - and they’re mostly imaginary!” My mentee was feeling very stressed - being in constant crisis is exhausting, and having to switch your attention every few days because there’s another fire to put out is terrible for productivity. I sympathized, and then my mentee asked if he should raise this with their boss’s boss - the skip level, or grandboss.

I invited them to follow that train of thought - what will the grandboss think when they hear this feedback? “Hm. Well, I suppose they’ll want to know what they can do to help?” That seemed optimistic. “Don’t you think your grandboss has enough problems? Why would they consider this a priority? Most people have “my problem” and “not my problem” mental categories - why would your grandboss make this their problem?” My mentee thought about this. “Well, because it’s affecting the team, and I can’t fix it”. “OK, let’s say that is how it plays out. What’s your grandboss going to do next?” “Uh - they’ll replace my boss, or get the training or something?” That again seemed optimistic. “Maybe, but don’t you think they will talk to your boss first, get their perspective?”. I saw the lightbulb go on.

“Managing up” is difficult. Sometimes, you end up with a boss you can’t work well with. Early in my career, I had a boss who was incredibly warm and caring, very much focused on personal development - but they were not “technical”, and thus the technical decision making was terrible. This meant lots of rework, lots of integration problems, and a reputation with other teams that we were flakey. When I raised it with my skip level boss - a very smart, career-driven operator who went on to become the CEO - he told me he knew (we had a high level of trust after working together on some challenging deadlines). “You think I don’t know? Your boss is a great human being, and has had a lot of success leading teams, but in this case, the work is too technical. I’m in regular meetings with you boss, and I’m aware of the problem.” I looked at my grandboss, waiting for the next sentence. My grandboss looked back. I ventured a very convincing “Eh, so…?” My grandboss sighed. “I’m aware of it. The situation persists. What do you conclude?”. I thought for a moment. “Either you’re working on it and can’t tell me, or you’re not working on it?”. “Okay, let’s see why I might not work on it?” I hated it when he did this. I was like being back at school. “Uhm…because there’s nothing you can do, or because you don’t think it’s the most important thing to work on right now. Maybe there are constraints I’m not aware of?”. And so I found out that, yes, my grandboss was aware of the problem, that they had a plan, but couldn’t tell me what it was, and that it would take a few months to play out.

I was very lucky - I had a grandboss who I trusted, and who was able to have this conversation in relative openness. They could easily have gone to my boss and discussed the feedback - and that would have made my position much harder. They could have told me to stop complaining and fix my own problems. They could have asked me if this was just personal animosity, and whether I had any specific examples. They could have insisted it was not a problem at all.

In short, when talking to skip level bosses about your own boss, I’d be very circumspect. Think through the next few steps that will follow your comments, stick to facts, and make sure you have a trust relationship.