Your "skip" is the person that your manager reports to - It's what happens when you "skip" your manager when going up your reporting chain. 1 on 1 meetings with your skip are tricky as you can't talk to them the same way you would to your direct manager:
Here's how you can get maximum value from your skip 1 on 1s:
- Understand your organization's overall strategy - Since your skip is operating at a higher-altitude, they will be naturally well equipped to answer this question. Ask them what their priorities are, and you can then weave them into your own work to increase your impact.
- Share "on the ground" insights - Skips are generally pretty disconnected from nuts and bolts day-to-day work due to their seniority. As an IC, you are well-equipped to share what that experience is like as that's your life. This is really valuable, if you can come up with insights on how to improve this experience.
- Be honest with feedback - There's not much value sucking up to your skip and telling them that they're great and everything is going great because of that. Be candid and unafraid to share real problems with how the organization functions.