What should I discuss in first 1:1 with my skip-level manager?

I would take this opportunity to find out what your skip level manager values. What kind of output to they want to see? What kind of problems do they want to solve? How can you help them, even if it's indirectly?

This will help you get more context and the big picture of things beyond your manager's scope.

Also, if this is your first meeting, take the time to share what your responsibilities are and what you're hoping to impact. What kind of issues can he come to you for? I would also take the time to learn what his responsibilities are and what he affects, along with what his goals might be.

Have you checked out this resource? https://www.jointaro.com/lesson/TToehFEc738PBhJcALwL/how-to-effectively-leverage-skip-level-11s/

Hope that helps!

I really like Xue's answer around simply asking what their priorities are and trying to understand the world through their eyes:

• It's fundamentally an empathetic exercise, and humans fundamentally value others who are seriously trying to understand their perspective.
• Even though you realistically don't have a ton of power to heavily affect their goals (don't worry, you'll get there someday!), the very act of asking has intrinsic value.
• You can augment all of this with active listening as I talk about here: Effective Communication Guide [Part 3.2] - Deep Listening

At a high-level, I would make the goal of this meeting about building trust and establishing yourself as a driven, talented individual in their eyes as opposed to trying to solve their problems or surface some genius-level insight they missed.

I hope these resources help as well:

• How To Effectively Leverage Skip Level 1:1s
• "How to make the most out of Director/VP/Exec office hours?"