Skip level meeting questions that are worth the awkwardness

A skip level is a strange meeting. You are talking to someone who does not report to you, about work you do not do, and their manager is sort of in the room even though they are not. Everyone knows that. Pretending otherwise is why so many skip levels end with twenty minutes of pleasant nothing.

The questions below are grouped by what I am trying to learn. I never use more than five or six in a single meeting. The point is not coverage, it is getting one honest answer that I could not have got from the org chart.

How to open so the answers are real

Say out loud what the meeting is and is not. Mine sounds like this: this is not a performance conversation, I am not collecting evidence about your manager, and I will not repeat anything you say here with your name attached unless you ask me to. Then keep that promise, because you get one chance at it.

Then say what you will do with it. If three people tell me the same thing, I will act on the theme, not the source. People are far more willing to talk when they know the mechanics.

What the work actually feels like

• What did you spend most of last week on, and was that the right thing?
• Which part of your week feels like wasted motion?
• If you could delete one recurring meeting, which one?
• What is slower than it should be, and who else notices?
• When something goes wrong here, what usually happens next?
• What do we do well that you would keep if we rebuilt the team tomorrow?

These pull out the process problems that never reach you, because the layer between you absorbs them. They stop working the second you start defending the process mid answer, so take the note, thank them and move on.

Whether they can see where the work is going

• In your words, what is this team trying to achieve this quarter?
• How does your current project connect to that?
• What decision from leadership made the least sense to you?
• What do you think we will be working on in six months?
• Where do you think we are quietly behind?
• What have you heard about the roadmap that you are not sure is true?

Ask these when you suspect the strategy is clear in your head and nowhere else. If the answer is wrong, resist reading it as a gap in the person, because it is almost always a communication gap in you.

Their manager, without asking them to grade their manager

• What does your manager do that helps you most?
• What would you like more of from your 1-1s?
• When you are stuck, who do you go to first?
• Is there anything you have raised more than once that has not moved?
• How do you find out about decisions that affect your work?
• If you needed two days off tomorrow, how easy would that conversation be?

The trick is asking about behaviour and mechanics rather than opinions. Nobody will tell a skip level that their manager is bad, but plenty of people will tell you they have raised the same thing three times.

What ruins it is taking one frustrated answer straight to the manager. That is how a skip level turns into a rumour engine, and how the next round gets you nothing.

Growth and staying

• What do you want to be better at a year from now?
• What work would you take if it appeared tomorrow?
• What are you learning right now, at work or outside it?
• Who here has taught you something recently?
• What would make you look at another job?
• What would make this the best year you have had here?

Only ask these if you intend to follow up. A growth answer with no consequence is worse than not asking, because it proves the meeting is theatre.

The room and the people in it

• Who on the team is doing work that goes unnoticed?
• Is there anyone you find hard to work with, and what happens when you do?
• How does the team handle disagreement?
• When did you last change your mind because of someone here?
• Who would you want on a project if it had to ship in three weeks?
• Is there anything the team jokes about that is actually a real problem?

That last question has produced more useful information for me than any other on this page. Teams turn their real complaints into jokes long before they raise them formally.

The closers

• What did you expect me to ask that I did not?
• What should I do differently after this conversation?
• Is there anything you want me to carry upward, with or without your name?
• What would make the next one of these more useful?

What to do in the week after

Write the meeting up within an hour, while you still remember the pauses. Separate what you heard from what you concluded, because a month later those two blur together and you will act on your conclusion as if it were evidence.

• Note the themes, not the quotes, if you promised anonymity.
• Pick one thing you can change within two weeks and say publicly that you changed it.
• Tell the manager the themes without the attribution, and tell them before you tell anyone else.
• Book the next round before the notes go cold.

Skip levels fail on memory more than on courage. You hear six people over two weeks, four of them mention the same release process, and by the time you sit down to act you remember two. Keeping a written record per person, and re-reading it before the next round, is the whole trick.

If you also run direct 1-1s, the same problem shows up weekly rather than quarterly. There is a longer list of questions for those in the guide on one on one meeting questions, and a walkthrough of cadence and preparation in how to run one on one meetings.