Holding a great skip-level 1:1
When I first started having skip-level 1:1s with my manager’s manager, I always found them a little scary. What could I possibly tell them that would be worth taking time out of their busy day? I’d often try to cancel, and if we did meet, I’d fill the time with status updates.
Now, as my team has gotten bigger, I find myself initiating skip-levels with people on my team. Meeting with people beyond my directs helps me get to know the entire team, and it gives me a better sense of how people are feeling and what’s happening around the org.
Remembering how hard it was for me to have those skip-level 1:1s myself, I now try to lay out my goals when I start them with any new person:
The time is theirs to use however is most useful to them. I’m investing time with them because I believe in their career and I want to spend time on whatever’s most helpful to them. I don’t need status updates — normally I already have other ways of getting that info, like reading regular roadmap updates or following dogfooding feedback.
Instead, these meetings are a great time to pull back from the day-to-day and talk about the big picture. It’s a chance for me to be a sounding board for what they want in their career and how I can support them, or for broader strategic questions that they want to talk through.
They can also help *me* during this time by telling me what they’re seeing that I’m not. As the org gets bigger, it’s harder for me to see everything that’s happening, and it’s also harder for people to give me direct feedback on what to do better. So I always appreciate hearing things happening around the team that I might not know — things going well, but even more importantly, things that aren’t going well like morale issues or execution hiccups, so I can understand and address them.
Now that I’ve started setting out these expectations for meetings with my team, I’m also more comfortable during my own skip-levels with my manager’s manager. After all, what’s the best use of that time? To help them help *me* in my career so I’m happy and more successful, or to get strategic context so I can be better at my job, or to flag issues that they might not see so they can decide how they want to take action on them.
I remember our skip chats! And also our conversation when I was trying to decide whether to go to HBS, which prompted a lot of reflection on my part. Framing how to best use the time upfront really does alleviate the stress / nerves that the team member feels when interfacing with someone at a higher level.
I remember you used to do skips with me. I bombed the first one bc I TOO was nervous and filled it with a status update that I had carefully prepared. At the end you said I didn’t have to do that…it was meant to be a more casual catch up. I was like …”oh!”