Skip-level questions for software engineers

Skip-level meetings are meetings at a regular cadence between yourself and the person two levels above you in the corporate hierarchy. Thus “skipping a level”. If you are a  software engineer who reports to a line manager, your skip level could a senior manager, a director, or even the CTO. It depends on the organizational structure where you work and who your manages your manager.

There are many articles that list questions for managers to ask during skip levels. But what questions should a software engineer bring to the table? Think about the goals of the meeting. What do you want to learn more about from their perspective in the organization? Here are some suggestions:

What do you think the top priority is on our larger team these days and why? (aka what problem is keeping you awake at night)

How do you think the priorities of the organization will change within the next quarter or the next year?

Bring a story to showcase your work during the meeting. Talk about a recent project you  worked on and the impact it had in a context calibrated to their interest. They might not care about the deep technical details of how you deprecated underutilized services or refactored a code base to reduce technical debt.  However, they will care that your project reduced infrastructure spend or made it easier for others to get up to speed and contribute to the code base.

Talk about your career aspirations and what’s interesting to you.  Sitting at a higher level in the organization, this manager probably has more visibility into opportunities on other teams than your direct manager.  If you let them know what other domains you’d like to explore, they can suggest your name when an opportunity arises.

If you’re interested in being promoted and this manager is part of the approval process, ask them about their perspective on the promotion process. Are there specific items on your engineering ladder that they view as especially critical? For instance, how do they view the importance of collaborating on cross-team projects, mentoring other team members, or presenting talks at conferences?

Conversely, the manager will probably ask for feedback on your manager and how they are performing in their role. This question can be a delicate balance because of the inherent power differential. Your manager decides how much you are paid, what projects you work on and writes your performance review.  However, managers need to improve their skill set too and the only way to do this is through feedback. If you feel safe to provide it through your skip-level meeting, please provide feedback on how your manager can better support you and the team. Knowing how to manage your manager, or “managing up” is a skill learned through practice and experience.

What other questions are useful in a skip-level meeting?

(Thanks to folks in the Rands leadership slack for suggestions on how to improve this post)