100+ Skip-Level Meeting Questions To Ask

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Do you have an upcoming skip-level meeting and wonder what topics to cover and what questions to ask? The topics may vary across companies, but there are some basic areas to tackle as a starting point. Let’s dive deeper into the essential skip-level meeting questions to cover at your next meeting.

How to Start? Common Icebreakers For Skip-Level Meetings

Starting a skip-level meeting with the right tone guarantees a comfortable and open atmosphere. Icebreaker questions can help build rapport, ease tension, and help you retrieve the honest opinions and ideas of the employees. Managers can establish trust by beginning with light, non-work-related questions, making it easier to delve into deeper topics later on. 

Icebreaker Questions:

1. What’s a hobby you’re passionate about outside of work?
2. What’s the best book or podcast you’ve come across recently?
3. If you could travel anywhere in the world right now, where would you go?
4. What’s one skill you’d love to learn and why?
5. What’s your favorite way to unwind after a long day?
6. What’s the most interesting thing you’ve learned this year?
7. Do you have any hidden talents?
8. If you could have dinner with any historical figure, who would it be?
9. What’s your favorite movie or TV show that you’ve watched recently?
10. What’s a goal you’re working towards outside of your professional life?
11. How do you usually spend your weekends?
12. What’s your favorite meal or type of cuisine?
13. If you could instantly become an expert in anything, what would it be?
14. What’s one thing you’re really proud of accomplishing?
15. How do you like to start your mornings?
16. What’s the best piece of advice you’ve ever received?
17. If you could live in any historical period, which would it be?
18. What’s your favorite way to stay active?
19. What’s one thing you’ve always wanted to try but haven’t yet?
20. What’s something you’re looking forward to in the next few months?

Skip-level Meeting Questions to Ask About Team Dynamics

As a manager you need insights about the team dynamics and overall workplace culture to identify potential conflics and focus on diminishing miscommunication at the company. It is good to ask open ended questions to reveal collaboration patterns and productivity drivers in the team.

Questions About Team Dynamics

21. How would you describe the current atmosphere within your team?
22. What do you think are the strengths of your team?
23. Are there any areas where you think your team could improve?
24. How well do team members collaborate on projects?
25. Do you feel that everyone’s contributions are valued equally in your team?
26. Are there any communication challenges within your team?
27. How does your team handle conflicts or disagreements?
28. Do you feel comfortable sharing your ideas and opinions in team meetings?
29. What do you think could be done to improve teamwork and collaboration?
30. How does your team celebrate successes and achievements?
31. Are there any recurring challenges that your team faces?
32. How well does your team adapt to changes or new processes?
33. Do you feel that your team is aligned with the company’s goals and values?
34. How well does your team share information and resources?
35. Are there any cliques or subgroups within the team that affect dynamics?
36. How does your team handle stress or tight deadlines?
37. Do you feel that everyone in your team is pulling their weight?
38. How does your team give and receive feedback?
39. What could be done to improve trust within your team?
40. How do you think your team could work more efficiently?

Skip-level Meeting Questions to Ask About Individual Challenges And Roadblocks

Roadblocks can negatively impact employee productivity and consequently affect overall company affairs. By talking about individual challenges at skip-level meetings, you can provide support, try to prevent production roadblocks. 

Questions About Challanges 

41. What’s the biggest challenge you’re currently facing in your role?
42. Are there any specific tasks or projects you find particularly difficult?
43. What are some obstacles that prevent you from doing your best work?
44. Do you feel like you have the resources you need to succeed?
45. Are there any tools or processes that could be improved to make your job easier?
46. How do you handle stress or high-pressure situations at work?
47. Are there any roadblocks that are outside of your control?
48. How do you prioritize your tasks and manage your workload?
49. Do you feel overwhelmed by your responsibilities at times?
50. How do you typically approach problem-solving in your role?
51. Are there any recurring issues that frustrate you in your work?
52. Do you feel supported by your manager and team when facing challenges?
53. What’s one thing that would make your job easier?
54. Are there any skills or knowledge gaps that you feel hinder your performance?
55. How do you stay motivated when facing difficult tasks?
56. Are there any interpersonal challenges with colleagues that affect your work?
57. How do you manage time-consuming tasks that pull you away from your core responsibilities?
58. Do you feel that your efforts are recognized and appreciated?
59. Are there any policies or procedures that you find burdensome?
60. What can I do to help remove any barriers you’re facing?

Skip-level Meeting Questions to Ask About Career Growth and Development

Asking about career growth and development perspectives at a skip-level meeting will showcase that the employee is valued at the company. Touching upon the employee’s long-term goals will help you better understand how the company’s objectives align with them and can impact the overall employee satisfaction rate. You can also offer tips or guidance on how to upskill to reach their desired career tops.

Questions About Career Growth 

61. What are your short-term and long-term career goals?
62. What skills would you like to develop or improve?
63. How do you see your role evolving in the next few years?
64. Are there any projects or tasks you’d like to take on to grow in your career?
65. Do you feel like you have the support needed to achieve your career goals?
66. What kind of training or development opportunities would you find valuable?
67. How do you prefer to receive feedback on your work and progress?
68. Are there any mentors or role models within the company you look up to?
69. How can the company help you achieve your professional aspirations?
70. Do you see yourself moving into a different role or department in the future?
71. What motivates you to continue growing in your career?
72. Are there any career paths within the company that interest you?
73. How do you measure your own success and progress?
74. What kind of challenges do you expect in pursuing your career goals?
75. Are there any certifications or courses you’d like to pursue?
76. How do you stay updated with industry trends and best practices?
77. What’s one thing you’d like to accomplish in your career within the next year?
78. Do you feel that your current role aligns with your long-term career goals?
79. How can your manager support your career growth more effectively?
80. What’s the most important factor for you when considering your career development?

Skip-level Meeting Questions to Ask Feedback On Leadership 

Another important goal of skip-level meetings is gathering feedback on leadership. This will help you understand how your actions and decisions impact the team. These questions provide insights into areas where leadership can improve, fostering a culture of continuous improvement and ensuring that leadership practices align with team needs and expectations.

Questions About Feedback On Leadership 

81. How do you feel about the communication between leadership and the team?
82. Are there any decisions made by leadership that you found confusing or unclear?
83. How would you describe the leadership style within the company?
84. Do you feel that leadership listens to and values employee feedback?
85. How well does leadership support your team in achieving its goals?
86. Are there any areas where you think leadership could be more effective?
87. How does leadership handle conflict resolution within the team?
88. Do you feel that leadership provides adequate recognition and rewards for hard work?
89. How transparent is leadership about company goals and performance?
90. How do you feel about the level of involvement leadership has in day-to-day operations?
91. Are there any leadership practices that you think could be improved?
92. How approachable do you find the leadership team?
93. Do you feel that leadership is aligned with the company’s values and mission?
94. How does leadership support your professional growth and development?
95. Are there any recent changes in leadership that have impacted your work?
96. How effectively does leadership manage change within the organization?
97. Do you feel that leadership is open to new ideas and innovation?
98. How does leadership handle difficult or challenging situations?
99. Are there any leadership qualities you particularly admire or would like to see more of?
100. How can leadership improve its relationship with the team?

Skip-level Meeting Questions to Ask About Innovative Ideas  

Creative ideas usually come from the bottom up, and they shouldn’t be missed if you care about your company’s growth.  Encouraging innovative ideas from employees will help you drive continuous improvement and stay competitive in the market.
This may not only leads to the development of new products, services, or processes but also enhances employee engagement and satisfaction.

Questions About Innovative Ideas

101. What’s one idea you’ve had recently that could improve our current processes?
102. Are there any new technologies or tools you think we should explore?
103. What’s one change you would make to how we currently do things?
104. How can we better serve our customers or clients?
105. Are there any trends in our industry that we should be paying more attention to?
106. What’s one thing you would do differently if you were in charge?
107. How can we improve the overall employee experience?
108. Are there any products or services you think we should consider offering?
109. What’s one process you find inefficient, and how would you improve it?
110. How can we make our meetings more productive and effective?
111. What’s one way we could improve collaboration across teams?
112. Are there any areas where you see an opportunity for innovation?
113. How can we better leverage data to drive decisions?
114. What’s one idea you have for reducing costs without sacrificing quality?
115. How can we improve our onboarding process for new employees?
116. Are there any partnerships or collaborations you think we should pursue?
117. What’s one thing you think our competitors are doing better than us?
118. How can we enhance our company culture to foster more creativity?
119. Are there any products or services you think we should discontinue or revamp?
120. What’s one thing we could do to stay ahead of industry changes?

Tips for Conducting Effective Skip-Level Meetings

Tip 1: Keep The Conversation Balanced

While it’s important to gather feedback, keep in mind that you should keep the balance. Skip-level meeting questions are only prompts to guide the conversation. Try not to make this meeting an interrogation but rather an open communication with empathy at hand. It would be great to recognize and celebrate successes, and then explore any challenges or suggestions the employee may have.

Tip 2: Respect Confidentiality

If an employee shares sensitive information, remember to respect their confidentiality. This will help build trust within the bigger team and not hinder the employee from sharing their real opinion. If your skip-level meeting is done remotely, follow video conferencing privacy measures.

Tip 3: Be An Active Listener

The primary goal of a skip-level meeting is to listen to employees’ perspectives. Practice active listening by giving the speaker your full attention, making eye contact, and acknowledging their points. Avoid interrupting and let them finish their thoughts before responding.

Tip 4: Take Notes

Taking notes during the meeting helps you capture important points and follow up on action items. You can install Krisp to use its AI meeting assistant when doing your skip-level meetings remotely. This will save you lots of effort and time as it automatically takes notes and generates AI meeting summaries. 

Frequently Asked Questions