Questions to Ask at a Skip Level Meeting
Strategic questions to ask your manager's manager in skip-level meetings to build visibility, share feedback, and advance your career.
1What are the most important priorities for our department right now?
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What are the most important priorities for our department right now?
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Why this works
Shows strategic thinking and helps you align your work with higher-level organizational goals.
2How does my work contribute to the bigger picture?
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How does my work contribute to the bigger picture?
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Why this works
Demonstrates interest in impact and helps you understand your role's strategic value.
3What skills or experiences would make me more valuable to the team?
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What skills or experiences would make me more valuable to the team?
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Why this works
Signals growth mindset and invites career development guidance from senior leadership.
4What challenges is our team facing that I might not be aware of?
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What challenges is our team facing that I might not be aware of?
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Why this works
Shows curiosity about broader context and willingness to help solve problems.
5How can I better support my manager?
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How can I better support my manager?
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Why this works
Demonstrates teamwork and gives insight into what leadership values most.
6What do you see as growth opportunities for someone in my role?
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What do you see as growth opportunities for someone in my role?
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Why this works
Opens conversation about career progression and advancement paths.
7Are there any concerns about my performance or approach that I should know about?
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Are there any concerns about my performance or approach that I should know about?
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Why this works
Shows maturity and openness to feedback from higher-level perspective.
8What qualities do you value most in high performers on this team?
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What qualities do you value most in high performers on this team?
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Why this works
Provides clarity on what success looks like from senior leadership's viewpoint.
9How does leadership view our team's performance?
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How does leadership view our team's performance?
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Why this works
Offers context about how your work is perceived at higher organizational levels.
10What projects or initiatives should I be aware of that might affect our work?
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What projects or initiatives should I be aware of that might affect our work?
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Why this works
Helps you stay informed about strategic changes and prepare proactively.
11How can I increase my visibility within the organization?
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How can I increase my visibility within the organization?
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Why this works
Shows ambition and asks directly for advice on building your professional brand.
12What feedback do you have about how our team operates?
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What feedback do you have about how our team operates?
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Why this works
Invites candid assessment that might not reach you through your direct manager.
13Are there cross-functional projects I could contribute to?
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Are there cross-functional projects I could contribute to?
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Why this works
Demonstrates initiative and desire to expand your impact beyond your immediate team.
14What's one thing I should start doing, stop doing, or continue doing?
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What's one thing I should start doing, stop doing, or continue doing?
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Why this works
Asks for specific, actionable feedback in a framework that's easy to answer.
15How has the company's strategy evolved recently, and what does that mean for us?
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How has the company's strategy evolved recently, and what does that mean for us?
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Why this works
Shows business acumen and interest in understanding strategic direction.
16What's working well from your perspective, and what could be better?
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What's working well from your perspective, and what could be better?
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Why this works
Opens space for both positive recognition and constructive observations.
17How can I better align my work with company values and culture?
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How can I better align my work with company values and culture?
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Why this works
Demonstrates commitment to organizational culture and desire to be a culture carrier.
18What resources or support does our team need that we're not getting?
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What resources or support does our team need that we're not getting?
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Why this works
Advocates for your team while giving leadership insight into operational needs.
19What advice would you give someone at my level looking to grow their career here?
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What advice would you give someone at my level looking to grow their career here?
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Why this works
Taps into their experience and gets personalized career guidance.
20Is there anything you'd like to know about my experience working here?
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Is there anything you'd like to know about my experience working here?
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Why this works
Flips the conversation and gives them valuable front-line perspective.
Best Practices for Skip-Level Meetings
Expert tips and techniques for getting the most out of these questions.
Best Practices
Prepare Thoughtfully
Come with a clear agenda and questions. This is a rare opportunity to make an impression on senior leadership.
Be Honest But Diplomatic
Share authentic feedback without throwing your manager under the bus. Focus on opportunities, not complaints.
Listen More Than You Talk
This is a chance to learn from someone with broader perspective. Ask good questions and absorb their insights.
Follow Up
If they offer advice or suggest actions, implement them and report back. Show you value their guidance.
Question Sequences
The Strategic Alignment Sequence
The Career Development Sequence
The Performance Feedback Sequence
Common Pitfalls
Don't Complain About Your Manager
Even if you have concerns, this isn't the forum. It will reflect poorly on you and damage trust.
Don't Waste Time on Small Talk
Be friendly but focused. These meetings are short—use the time strategically.
Don't Just Ask for Promotions or Raises
Focus on how you can add value, not just what you want to get. Career growth follows contribution.
Don't Be Unprepared
Showing up without questions or agenda suggests you don't value their time or the opportunity.