165 Skip-Level Meeting Questions: Strategic Questions for Every Perspective

A skip-level meeting is more than just a conversation; it's a strategic tool for breaking down hierarchical barriers, fostering transparency, and gaining an unfiltered view of your organization's health.

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When executed well, these meetings can dramatically improve manager effectiveness, employee retention, and operational efficiency.

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The key to a successful skip-level meeting lies in asking the right questions.

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This definitive guide provides a curated bank of over 150 questions to help managers and employees prepare for productive, insightful, and action-oriented conversations.

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Why Skip-Level Meetings Are a Strategic Imperative

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Skip-level meetings are not about micromanagement. They are a critical leadership practice that serves several vital functions:

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• Build Trust and Transparency: They signal to employees that leadership is accessible and genuinely values their perspective.

• Develop Your Leaders: They provide anonymized, high-quality feedback you can use to coach your direct reports.

• Uncover Ground Truth: They reveal cultural issues, operational bottlenecks, and team dynamics that often remain hidden in formal reports.

• Improve Retention: Employees who feel heard and seen are significantly more likely to be engaged and stay with the company.

• Align Strategy: They ensure that company goals are understood and that every team is working in concert to achieve them.

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The Golden Rules for a Psychologically Safe Meeting

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Before you ask a single question, you must create an environment of trust and safety. Without it, you will only get surface-level answers.

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1. Brief Direct Managers Transparently: Reassure your direct reports that these meetings are for their development and organizational health, not an inspection. Get their buy-in beforehand.
2. Ensure Anonymity & Confidentiality: Open the meeting with a clear, reassuring statement: "This is a confidential conversation. Your honesty is both valued and protected. Nothing you say will be shared with your manager or anyone else in a way that identifies you, without your explicit permission."
3. Listen to Understand, Not to Respond: Your primary job is to absorb information. Suspend the urge to justify, explain, or solve problems in the moment. Practice active listening.
4. Commit to Taking Action: Take visible notes. Promise to look for themes and follow up. Feedback without visible action erodes trust faster than no meeting at all.

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How to Use This Ultimate Skip-Level Question Bank

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This resource is a strategic menu, not a checklist. Do not attempt to ask all 165 questions.

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For a 45-60 minute meeting, follow this agenda and select 5-7 questions total:

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• 5-10 mins: Build Rapport (Choose 2 questions from Category 1)

• 20-30 mins: Primary Focus (Choose 3-4 questions from one other category)

• 5-10 mins: Secondary Focus (Choose 1-2 questions from a different category)

• 5 mins: Closing (Always ask the 3 questions in the final category)

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Skip-Level Questions for Managers to Ask Employees

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Building Authentic Rapport & Personal Connection

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1. What was the highlight of your week so far?
2. What’s a hobby or interest you’re passionate about outside of work?
3. What’s the best book you’ve read recently?
4. What’s a podcast you’re currently hooked on?
5. What show are you binge-watching right now?
6. What is your idea of a perfect weekend?
7. What is the most memorable trip you’ve ever taken?
8. If you could travel anywhere tomorrow, where would you go?
9. What’s the best meal you’ve ever had?
10. Who is your favorite musician or band of all time?
11. What was the first concert you ever attended?
12. What’s a fun or interesting fact about you that not many people know?
13. What are you most proud of in the last year, personally?
14. How do you like to recharge after a long day?
15. If you could have a superpower, what would it be and why?

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Manager's Leadership & Communication Style

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16. What is one thing your manager does exceptionally well?
17. What is one thing your manager could improve on?
18. How would you describe your manager’s leadership style?
19. How effective is your manager at communicating goals and expectations?
20. Does your manager provide clear and actionable feedback?
21. How does your manager handle it when you make a mistake?
22. How does your manager act during high-pressure or crisis situations?
23. Does your manager empower you to make decisions?
24. Do you feel micromanaged or trusted in your role?
25. How does your manager recognize and celebrate your wins?

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Manager's Support & Development Focus

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26. How does your manager support you when you’re struggling?
27. Is your manager approachable and available when you need them?
28. How does your manager support your career development?
29. Does your manager help you get access to resources and training?
30. Do your 1:1 meetings with your manager feel valuable? Why or why not?
31. What percentage of your manager's feedback is positive vs. constructive?
32. Does your manager publicly credit team members for their work?
33. How does your manager handle underperformance on the team?
34. Does your manager advocate for the team to upper management?
35. On a scale of 1-10, how would you rate your manager’s effectiveness? Why?

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Team Culture & Psychological Safety

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36. On a scale of 1-10, how would you rate team morale? Why?
37. How would you describe the team’s culture in three words?
38. How effectively does the team collaborate?
39. Is there a sense of trust and safety within the team?
40. How does the team handle disagreements or conflict?
41. Are team meetings productive and engaging?
42. How are decisions made within the team?
43. Does everyone on the team pull their weight?
44. Without naming names, is there a perception of unfairness in workload?
45. Who on the team is an unsung hero?

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Team Processes & Collaboration

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46. How inclusive is the team environment?
47. Do team members socialize outside of work?
48. How does the team onboard and support new members?
49. What is the team’s biggest strength?
50. What is the team’s biggest weakness?
51. What is one thing the team should start doing?
52. What is one thing the team should stop doing?
53. What is one thing the team should continue doing?
54. How does the team celebrate successes?
55. How does the team handle failures?

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Daily Workflow & Tools

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56. What is the biggest bottleneck in your daily work?
57. What process is overly complicated or bureaucratic?
58. What tool or software is missing from our stack?
59. What existing tool or software is ineffective?
60. What meeting could be eliminated or improved?
61. How much time do you spend on "work about work" (reporting, updating trackers)?
62. How easy is it to get a decision made?
63. How easy is it to get a budget approved?
64. How easy is it to get a resource you need?
65. What always seems to fall through the cracks?

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Strategic Alignment & Resources

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66. If you were CEO for a day, what's the first operational change you'd make?
67. How effective is our internal communication?
68. What information do you not have access to that you need?
69. How clear are our goals and priorities from a company level?
70. How does strategy get translated into actionable work for your team?
71. What is the biggest gap between strategy and execution?
72. What is the biggest risk to our projects that nobody is talking about?
73. How effective is our project management?
74. How effective is our knowledge management (e.g., Wikis, documentation)?
75. Is it easy to find information you need?

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Personal Enjoyment & Strengths

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76. What do you enjoy most about your current role?
77. What do you enjoy least about your current role?
78. What are your short-term career goals (1-2 years)?
79. What are your long-term career goals (3-5+ years)?
80. Do you see a path to achieve those goals here?
81. What skills would you like to develop right now?
82. What skills are you not using that you’d like to use?
83. What type of work energizes you?
84. What type of work drains you?
85. What part of your job would you like to do more of?

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Growth & Retention Drivers

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86. What part of your job would you like to do less of?
87. What kind of training would be most beneficial for you?
88. What conference would you love to attend?
89. Who in the company would you like to learn from?
90. Are you interested in finding a mentor?
91. Are you interested in being a mentor?
92. What does your ideal next role look like?
93. Do you feel you are paid fairly for your role and experience?
94. How do you feel about your benefits package?
95. On a scale of 1-10, how excited are you about your future at this company?

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The Non-Negotiable Closing Questions

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96. Of everything we discussed, what was the most important topic for you?
97. What is one specific thing you will hold me accountable to follow up on?
98. Is there anything we didn’t talk about that you thought we would?

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Skip-Level Questions for Employees to Ask Skip-Level Managers

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Understanding Leadership's Perspective

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99. What do you enjoy most about your role?
100. What’s the biggest challenge in your role?
101. What does a typical day look like for you?
102. How did you get to where you are in your career?
103. What was your first role at this company?
104. What’s the best career advice you’ve ever received?
105. Who has been a mentor to you?
106. What’s a book that has significantly influenced your leadership style?
107. What’s a failure you expeexperienced, what did you learn from it?
108. What are you most proud of in your career?

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Seeking Performance Guidance

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109. From your perspective, what are the most valuable skills in my role?
110. What skills will be most important for the future of my department?
111. How do you define success for someone in my position?
112. What are the key performance indicators (KPIs) you care most about for our team?
113. What does "exceeding expectations" look like for my role?
114. What opportunities do you see for me to have a greater impact?
115. Are there any projects you’re aware of that could use my skillset?
116. What is a problem you’re trying to solve that I could help with?
117. How can I better align my work with the company’s top priorities?

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Navigating Career Paths & Advancement

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118. What is one thing I could do differently to be more effective?
119. What is one thing I should keep doing because it’s highly valuable?
120. How can I improve my visibility and influence within the company?
121. Who would you recommend I connect with to learn more about [X]?
122. What training or certifications would you recommend for me?
123. How can I prepare myself for a potential future leadership role?
124. What are the biggest challenges someone at my level faces when trying to advance?
125. What are you looking for when you consider someone for promotion?
126. How does the promotion process truly work?
127. What is the most common reason why people don’t get promoted here?

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Company Strategy & Future Vision

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128. In your own words, what is the company’s most important goal this year?
129. What is the company’s biggest competitive advantage right now?
130. What is the company’s biggest weakness or threat?
131. What are you most excited about for the company’s future?
132. What keeps you up at night regarding the company?
133. How does the strategy you’re working on translate down to my team’s goals?
134. How can employees at my level contribute to the company’s long-term vision?
135. What does the company’s five-year vision look like?
136. How do you see our industry changing in the next five years?
137. How is the company preparing for those changes?

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Culture, Values & Operational Direction

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138. What does our company value most: innovation, efficiency, customer focufocus, orething else?
139. How are the company’s values actually used in decision-making?
140. Can you give an example of a tough decision where values played a key role?
141. How is the company working to improve diversity, equity, and inclusion?
142. What is the company’s philosophy on remote and hybrid work?
143. How does the company think about its social responsibility?
144. What is the biggest cultural challenge the company faces?
145. What is one thing you would change about the company’s culture if you could?
146. How does the company encourage innovation and new ideas?
147. What happens when someone fails at a new idea here?
148. How does the company make sure it’s listening to employees?
149. What was the best piece of feedback from employees that led to a real change?

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Departmental Priorities & Challenges

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150. What is the biggest priority for our department right now?
151. What is the biggest challenge our department is facing?
152. How does our department’s work impact the company’s bottom line?
153. How could our department collaborate more effectively with [X department]?
154. What is another department doing really well that we could learn from?
155. What are the biggest inefficiencies you see in our department?
156. What technology or tools are we missing that could help us?
157. Are there any new roles or teams being planned for our department?
158. How is our department performing against its goals?
159. What is a new skill our department needs to build?
160. How do you see our department evolving in the next two years?
161. What is the biggest opportunity our department is not yet pursuing?
162. What is the biggest misconception other departments have about us?
163. How can I help improve collaboration between my team and others?
164. What is one thing I can do to help our department be more successful?
165. Is there anything else about the department’s direction I should know?

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After the Meeting: From Conversation to Action

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The real work begins after the meeting. Your follow-through is what builds lasting trust.

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1. Synthesize & Identify Themes: Review your notes across all meetings. Look for common patterns, not isolated complaints.
2. Coach, Don't Punish: Use the feedback from the manager-focused categories to coach your direct reports. Frame it as developmental data: "I've heard from a few team members that..."
3. Address Systemic Issues: Take themes related to operations and strategy to other leaders. Champion changes that remove roadblocks for everyone.
4. Close the Loop: Follow up with the employees. Send a summary of the themes you heard and the actions you are taking. This step is non-negotiable.

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Conclusion: The Power of Asking

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The right skip-level meeting questions are your greatest tool against the isolation of leadership.

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By asking with genuine curiosity and listening with empathy, you stop being a distant executive and become a connected leader.

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You build a culture where every voice feels heard, every manager is supported, and the entire organization moves forward, aligned and empowered.

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Use these questions not as an interrogation, but as an invitation to a deeper, more honest conversation.