Skip-Level Meeting: 21 Questions to Ask Your Boss's Boss

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Every now and then, you may be asked to have a one-on-one meeting with your manager’s boss, which is referred to as a ‘skip-level’ meeting. This might be alarming to some if no reason or explanation for the invitation is given. 

Not to worry! Skip-level meetings are a leadership tool that is increasingly recommended by experts to improve communication and productivity throughout an organization. By participating and bringing your unique perspective to the meeting, you will have the opportunity to make more of an impact at your company.

You may be wondering what will be brought up during a skip-level one-on-one with a senior leader. It should be similar in structure to a regular one-on-one meeting with your manager, and you will likely be asked to prepare an agenda and bring your questions and concerns to the table.

Don’t stress too much over the idea of meeting with a higher-up, but spend some time on preparation in order to provide credible and useful insights. Below are some topics you can focus on in a skip-level meeting, including sample questions to ask your boss’s boss.

Strategy

1. Can you talk about the company’s direction and vision?

2. What are some ideas you would like to implement in the future?

3. Do you agree with the current strategies we are pursuing?

4. How often does upper management meet to talk strategy?

5. Are there any industry trends that are worrying right now?

6. How does our team support the company’s overall mission?

Alignment

1. What are you hoping to achieve in our department this quarter? This year?

2. Which things are most important for our team to prioritize?

3. How can we better contribute to the organization?

4. What can I do to help with any issues?

5. What would you do if you were in my shoes?

6. Do you have any recommendations about how I can gain a better understanding of _______?

Feedback

1. What kind of feedback is most useful to managers?

2. Is there a system in place for feedback to move up the chain of command?

3. How can I receive more detailed feedback from my manager?

4. Were you satisfied with the outcome of [past project]?

5. Would you recommend any changes to improve our department’s processes? 

Career Development

1. What was your career journey like here at [company]?

2. What are some of the most important steps I can take at this stage in my career?

3. Do you look for certain traits or skills when appointing leadership roles?

4. Are my goals for advancement reasonable?

Be sure to come to the skip-level meeting with an enthusiastic, inquisitive attitude. The senior manager will likely have questions of their own, so be attentive and answer as candidly as possible. Steer clear of airing complaints or criticisms of your manager and other coworkers. Skip-level meetings are mostly a way for senior managers to get a new perspective on broad organizational level issues from employees they don’t often hear from. If you can offer those insights in a clear and memorable way, you are sure to impress your senior manager in a skip-level meeting. 

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