Topics to talk in 1:1 with skip level manager?

Alex and Rahul definitely touched on the most important topics to tackle during skip level 1:1s! I would only add 1 more potential topic and 1 concern from my side.

Topic: how would you describe a great engineer at my level at my team and what will it be different to be a successful engineer at the next level at my team?

Concern: I recommend being very careful when you complain about your manager to your skip-level.

• If you have a great manager and just see a growth area for them, then it will be much better for both of you to deliver this feedback directly to your manager (in a polite and caring manner of course)
• If you don't have a good manager (from your point of view), then it would be still better to deliver your concerns to your direct manager first. Also consider keeping shared notes for 1:1s with your direct manager. And if they don't deliver even on the written notes you both track, then it could be a much more productive conversation with your skip-level (starting from sharing about your efforts to improve the relationship in 1:1 manner and following on the specific areas that are mentioned in your doc, but are still lagging). Also it's important to mention, that your direct manager most likely has weekly 1:1s with your skip-level and it's in your interest for them to have a good rapport. So coming with complains can deteriorate relationships between you and your direct manager + between your direct manager and their manager which can often limit your own career opportunities. So I would say that such approach should be the last level of resort and building trust with you direct manager could serve you better in a long-term.

I think the core operating principle here is don't talk about the same topics you talk about with your manager. Your skip is operating at a higher altitude, so your goal is to try to see the world through their eyes at this altitude and reverse-engineer questions that tap into this perspective.

All that being said, here's some ideas on what to talk/ask about:

• Org priorities - This can manifest as a simple "What's the biggest focus for you going forward?" or "What keeps you up at night?". This won't be as concretely actionable as a mid-level engineer, but it's still very nice to know. It will become very important to know once you're a senior engineer and effectively a requirement to understand if you're pushing for staff.
• Feedback about org culture and process - This is really important as it's a huge part of your skip's job to solve these problems. Let's say your team is regularly having problems shipping projects, because you constantly hit some unexpected compliance issue very late into execution, and this delays launches by quarters and even halves. This is something you should mention to your skip as this is likely to be a systemic problem across the org. If your skip can solve it, that's the multiplicative impact they are expected to have and it's a win-win for everyone (the skip gets the impact and your team is now more empowered to ship).
• Thoughts on your manager - If you have feedback on how your manager can improve, that's very relevant for your skip as they are your manager's manager (I've had skips ask me proactively "So Alex, what do you think about your manager?" in 1:1s many times). What may be less obvious - Even if you have no constructive criticism about your manager and you just think they're completely crushing it, let your skip know as well! They'll be happy to know that their report is doing very well, and this is also useful tactical information as good managers will be given more scope. Positive energy is almost always super helpful!

Related resources:

• How To Effectively Leverage Skip Level 1:1s

One question I like to ask a skip-level manager: what are the biggest risks to hitting the team goals?

This helps you understand their concerns. Evaluate if you agree with them (and push back if you disagree!), but this also gives you ideas around what projects may be most impactful to help de-risk the goals.