Skip level meeting questions to ask your boss's boss

Most of what is written about skip levels is written for the senior manager running them. If you are the one being invited, the advice is thin: be honest, do not badmouth your manager, bring questions. Fine. Which questions? Here is what I would want someone two levels down from me to ask, written from the other chair.

First, what the meeting is for. Your skip level manager is not checking up on your boss and is not evaluating you. They want two things: a view of how the work feels one layer down, and a sense of who you are, because at some point they will be in a room deciding things about your career without you in it. That second part is the one people underuse.

Questions about where the team is going

• What is the one thing you would like this team to be known for a year from now?
• Which of our current projects matters most to you, and why that one?
• What are you worried about that we probably do not see from here?
• If budget or headcount changed next quarter, what would you cut first and what would you protect?

These do two jobs. You learn what your boss's boss optimises for, which tells you what good work looks like in their eyes. And they see you thinking above your own backlog, which is most of what senior means to someone at that level.

Questions about your own path

• What did the people who grew fast here do differently?
• What would you need to see from me before you would back me for the next level?
• Is there a problem in the org that nobody owns and that someone like me could take?
• Who do you think I should be learning from?

Ask the second one straight. A vague answer means they have not thought about you yet, which is worth knowing, and asking is what makes them start.

Questions about how things work

• How do decisions that affect my team get made, and where could I have input?
• What did leadership decide recently that you wish we understood better?
• What do you wish people on my team escalated sooner?
• What is the best way to get something to you when my manager is out?

Questions about them

• What is keeping you busy that we do not see?
• What did you get wrong in your first year in this role?
• What is a hard call you made recently?

Almost nobody asks their skip level anything about themselves, and it is the quickest way to be remembered. Do not fake interest. One of these is enough.

What to leave out

Do not bring a complaint about your manager unless something is seriously wrong and you have already said it to them directly. A skip level is not the channel for it, and it will travel back to your manager in a shape you did not choose. Do not ask for a raise or a promotion in the meeting. Ask what it takes, which is a different question and gets a real answer. And do not fill the time with status, they can get that from your boss in two minutes.

Before and after

Pick three questions, not twelve, and lead with the one you most want answered, because skip levels run short and the first ten minutes are the honest ones. Afterwards write down two things: what they said about priorities, and what they said about you. Half of it will matter in six months and you will not remember it otherwise.

If you are the manager running these rather than the one invited, the longer list of skip level meeting questions is written from your side, with what the good answers sound like, and the skip level meeting template covers the whole meeting.