Skip level meeting questions to ask your boss are best kept to three: one about where the business is heading, one about your own growth, and one about the person across the table. Below are 30 to choose from, grouped by what you want to learn.
Illustrative example
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Before a question goes on your list, check it against these three.
Strategy, trade-offs, what worries them. Your manager can tell you what's due on Friday. This person can tell you why it's due at all.
If the answer wouldn't change what you do next month, swap the question for one that would.
How they like to hear bad news, what a good week looks like for them. People remember who was curious about them.
Tick up to three. They collect in the "My three questions" box, and one tap copies them into your notes. Each group names the motivators of people who tend to ask those questions first, so if you know your own top motivators, start with that group.
Often first for people high on Rationality or Security
Often first for people high on Status or Feedback
Often first for people high on Progress
Often first for people high on Autonomy or Innovation
Often first for people high on Social
Worth one of these whatever your motivators
Chefs call it mise en place: every ingredient chopped and measured into its own little bowl before the first order comes in, so service is spent cooking instead of hunting for the paprika. A skip-level runs the same way. Most of the half hour belongs to the hellos and to their questions. What's left is roughly twelve minutes, and it goes to whoever turned up with their bowls already filled.
Illustrative split. Your meeting will vary, but the share left for your questions rarely gets bigger.
Each of these is a fair thing to want to know. Asked straight, most get a polite non-answer. Asked this way, they get something you can use.
| Instead of | Ask |
|---|---|
| "Am I getting promoted?" | "What would you need to see from someone at my level to be ready for the next role?" |
| "Are there layoffs coming?" | "What's changing in the next six months that I should be getting ready for?" |
| "Can you do something about my pay?" | "How are pay and levels decided here, and who should I talk to about mine?" |
| "What do you think of [colleague]?" | Leave it out. Ask about the work, and let people speak for themselves. |
| "Why is my manager like this?" | Describe the pattern with dates and leave the verdict to them. Our main skip-level guide covers how to prepare for a skip-level meeting as an employee, including how to raise a manager problem. |
The meeting is half the job. A two-line note afterwards is what makes them remember the conversation, and it takes ten minutes.
Thank them for the time, and name the one thing you'll do because of what they said.
Share the topics and skip the play-by-play. Hearing it from you first keeps it from feeling like it happened behind their back.
Open the next skip-level with what you did about it, including the parts that didn't work. A leader who levels with you notices when you level with them.
The other chair is harder. You're asking people two levels down to be candid with someone who can change their year, and most of them will tell you everything is fine. Our guide to skip level meeting questions has 45 for leaders, a 30-minute agenda and what to do with the answers.
It also helps to know what each person cares about before you sit down. Attuned maps every person on 11 intrinsic motivators in a roughly 10-minute assessment, so you know whether to open with growth, autonomy or the plan. Before the meeting, the AI coach for managers suggests an opening question for that person.
Illustrative example
"Being able to get to the nub of people's underlying motivations has been very helpful."
Kevin HalliganAssociate Director, Azon Recruitment Group · Read the storyBring us one team. We'll map each person's intrinsic motivators and show you how to open the conversations that usually end in "all good".
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