Questions to ask your boss’s boss in a skip-level meeting

You check your work calendar and see you’re scheduled for a skip-level meeting with your boss’s boss. What are skip-level meetings, and how can you prepare for them? Skip-level meetings veer from the normal structure of check-ins by giving you a chance to speak with the superior above your superior. This can be a great opportunity to learn more about them, make a connection, and discuss your career growth within the organization. Here’s what you need to know about skip-level meetings and which questions to ask your boss’s boss.

What is a skip-level meeting?

A skip-level meeting is a one-on-one in which the team member meets with their boss’s boss instead of their immediate supervisor. For example, this may mean a graphic designer may meet with the marketing department manager instead of with their normal team leader. The “skip” in skip-level can go as far as the organization wants, which means you could potentially meet with your boss’s boss’s boss.

Who can take part in a skip-level meeting?

Who takes part in a skip-level meeting can vary depending on the company. Anyone in a company can take part in skip-level meetings, all the way up to the CEO, if that’s what’s best for the organization. Participating in skip-level meetings may be beneficial for leaders as it can help them connect with team members and learn more about what teams are doing. Involving more people in skip-level meetings can help businesses create a strong workplace culture.

Are skip-level meetings bad?

When management schedules you for a skip-level meeting, it doesn’t mean you’ve done something wrong. Skip-level meetings are a tool that companies can use to strengthen their workplace culture and help employees form relationships. Communicate with your colleagues and leaders to learn more about what skip-level meetings mean at your organization.

How often do skip-level meetings happen?

Every company can develop different frequencies for skip-level meetings. Smaller organizations may choose to have less frequent skip-level meetings as they may have fewer opportunities to meet and engage with new leaders. Businesses may schedule skip-level meetings bi-weekly, monthly, or quarterly, depending on their goals and size.

Preparing for a skip-level meeting

Prepping for the meeting can help you make the most of your time and make a good impression on your boss’s boss. These are some steps you can follow to prepare for your next skip-level meeting:

Learn more about your boss’s boss

Before your meeting, consider learning more about who you’re meeting with. You can find their profile on professional networking sites or review their information in the company documents, like the handbook or employee registry. It can be helpful to review who they are and what they do so you can focus on the most important questions during the meeting. Learning more about them before the meeting can also help you show your interest and preparedness.

Stay positive and focus on relaxing

You may be nervous about the idea of meeting with your boss’s boss, especially if it’s someone you haven’t interacted with much before. This is part of what makes skip-level meetings effective as it gives you the opportunity to relax and get to know the person you’re meeting with. Consider taking deep breaths and reminding yourself that the meeting is an opportunity to introduce yourself and learn more about your career within the company.

Determine what you want to share

It’s a good idea to introduce yourself and share some information about your goals and career during your meeting. Before the meeting, make a list of the information you’d like to share. For example, you may jot down basic information about who you are and what you do, your career goals, and where you’d like to be in five years. Making a list before the meeting can help you ensure you share everything you wanted to within the time frame.

Prepare effective questions to ask

Besides sharing information about yourself, skip-level meetings also give you an opportunity to learn more about upper management. Omit questions that don’t give you new information. For example, if you discovered during your research which university your boss’s boss attended, avoid asking them where they went. Instead, you may ask them how they liked it or if they would choose it again. Researching, determining what you want to share, and writing a list of questions to ask can help you be prepared and make the most of your time.

“When management schedules you for a skip-level meeting, it doesn’t mean you’ve done something wrong. Skip-level meetings are a tool that companies can use to strengthen their workplace culture and help employees form relationships.”

Benefits of skip-level meetings

Skip-level meetings may seem scary when you learn you’re meeting with your boss’s boss, but they’re effective for improving the workplace. These are some reasons your organization may have implemented skip-level meetings:

• Better communication: Skip-level meetings can help establish healthy relationships and facilitate effective communication between team members and managers.
• Improved leadership: When leaders meet regularly with those they’re managing, they can adjust their approaches based on the information they learn.
• More staff feedback: Gathering feedback from team members can help management create a more inclusive environment. 
• Boosted engagement: When staff members feel like their ideas, questions, and voices are heard, it can help to boost engagement, productivity, and satisfaction.

15 questions to ask your boss’s boss

One way you can prepare for your meeting is to make a list of potential questions to ask. These are some questions to ask your boss’s boss:

1. What’s your process for giving effective team feedback?
2. Why did you choose this career? Why did you choose this industry?
3. How long have you been working in this field?
4. Where are you from? Where did you grow up?
5. What do you think are the most essential soft skills I can develop?
6. What was your major in college? Did you ever switch your major?
7. What’s something about this organization you think should change?
8. Can you tell me about the company’s current vision?
9. What do you think this company will look like in five years?
10. What’s the difference between your position and my manager’s position?
11. What would you say is the biggest challenge you face?
12. Do you have any feedback on my team’s last project?
13. What’s on your mind right now when it comes to this organization?
14. What was your career journey like here? Where did you start out?
15. Do you think my professional goals are achievable or reasonable?

Tips for improving skip-level meetings

These are some tips you can use to improve your next skip-level meeting:

• Develop an agenda together: When leaders and team members work together to develop an agenda, it can help ensure the skip-level meeting serves both parties.
• Review the time you have: Before meeting with your boss’s boss, check to see how long the meeting will be. This can help you prioritize your most important questions.
• Don’t be afraid to ask questions: If you have questions about the organization or your current career goals, don’t be afraid to ask them. That’s what skip-level meetings are for.

Learning which questions to ask your boss’s boss can help you better navigate skip-level meetings. If talking with upper management helped you figure out your career goals, create a profile so employers can find you and chat with you about potential roles.

More tips for skip-level meetings:

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Relax before your skip-level meeting by taking a walk or listening to music.

Discover the best ways to talk to your boss’s boss about your career goals.