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101+ Skip-Level Meeting Questions - A Leader's Guide đź’¬

Skip-level meeting questions to build rapport, gather feedback, and identify top performers.

101+ Skip-Level Meeting Questions - A Leader's Guide đź’¬

What makes a good skip-level meeting question depends on what you’re trying to learn.

Do you want to find areas where your managers can improve? Do you need insight into how the team is working together? 

Maybe you want to find out who deserves recognition... Or you’re just looking for common ground to build rapport with your junior employees. 

In any case, achieving the objective of your skip-level meeting requires the right question. So in the following paragraphs, I'll outline questions (along with explanations) categorized by your skip-level objective.

Questions to Build Rapport before Diving In

As I explained in this guide on skip-level meetings, leaders must build rapport with junior employees to have an effective meeting. 

After all, sharing ideas and discussing your manager’s performance with their boss can be nerve-wracking. Building rapport helps establish trust which leads to more useful feedback.

The following is a list of questions you can use to get to know junior employees:

  1. What motivates you to do your job?
  2. Where did you go to college? (OR) Where did you grow up?
  3. What’s the best book, podcast, or movie you’ve recently read, listened to or watched?
  4. (If they have children) How is (name of child) doing?
  5. What do you like to do when you’re not working?
  6. Do you have any trips planned? (OR) Have you been on any trips lately?

The key here is to get them talking and to have fun. If you can find common ground, such as a shared interest, hometown, or college, the rest of the conversation will be much easier. But simply showing interest in people tends to yield better results, even if it’s awkward at first.

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Questions to Inform Manager and Team Feedback

As important as building rapport is, your skip-level meetings should be mostly about how you and your team can do better. Scott Boulton, a Human Resources Manager recommends discussing the following questions: 

  1. What works well in the department right now? (i.e. systems, processes, technology, feedback, etc.)
  2. What needs improvement and/or what obstacles are preventing you from being successful? (i.e. technology, top-level support, more feedback, etc.)
  3. What is one thing, as a department, we need to start doing right away to be more successful?
  4. What is one thing, as a department, we need to stop doing right away to be more successful?
  5. What is one thing, as a department, we need to make sure we continue to do in order to be successful?
  6. What do you need more or less of from your manager or myself in order to be successful as a department and in your role?

As you may notice, all of Boulton’s questions are specific and they require elaboration, not “yes” or “no” answers. In a Harvard Business Review article, Carolyn O’Hara also underscores the importance of being specific and avoiding yes/no questions when soliciting feedback.

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For example, she advises against asking general questions like, “Do you have any feedback for me?” Instead, she recommends asking specific questions such as:

  1. What’s one thing your manager or I could improve on?
  2. What’s one thing your manager or I could have done to make that meeting, presentation, or project go better?
  3. How did [name of project] go from your perspective?
  4. What do you think your manager or I could’ve done differently on [name of project]?
The more we question, the better answers we get.

Michael Brown, Regional General Manager at Uber also offers the following ideas for questions to ask in skip-level meetings:

  1. What is the morale in the office from your point of view?
  2. How are you feeling about your team?
  3. What obstacles are you facing in your job?
  4. Do you understand the company’s goals and how your team’s goals fit into that picture?
  5. Do you feel like you can do things you believe are right for the business?
  6. Do you think leadership acts consistently with your values?
  7. What would make work better for you?
  8. When was the last time you took a vacation?
  9. What is your sacred space? Do you feel like you have time for it?

Questions to Identify Top-Performers

Praise is a proven and affordable way to improve employee engagement, but how do you know who to praise as a senior leader? 

The Lighthouse blog explains that you can find hidden stars by asking the right questions. Here are a few they recommend using to find out who deserves praise:

  1. Who do you enjoy working with most on your team? Why them?
  2. Who has done awesome work lately? How did they contribute?
  3. Who is an unsung hero in our company? What do they do that deserves recognition?
  4. What is the greatest strength of your team? Who personifies that best?
  5. Who on your team makes those around them better? How do they do it?
  6. If you were forming a new team, who are the people you’d most want on your team? Why them?

As a leader, being at least one organizational level removed from the front lines makes it hard to know who your stars are. These questions help you uncover the unsung heroes you’ll want to invest in.

70+ More Skip-Level Meeting Questions

When we started this list, we only had a paltry 31 questions. That simply wasn't enough.

1. What was your favorite part of the workday?
2. What was your least favorite part of the workday?
3. Who did you interact with today and what was that interaction like?
4. What are you looking forward to in the coming week?
5. How could we have helped you better this week?
6. What surprised you most about your job this year?
7. Tell me about the best client/customer interaction you had recently.
8. What was one of the hardest situations you faced this month and how did you handle it?
9. Where do we need to be better tomorrow?
10. What are your top 3 goals for the coming weeks?
11. What do you like most about this company?
12. What do you hope to change in the next year?
13. Tell me about a time that you left work feeling happy or successful. Why was that so rewarding for you?
15. What is your biggest victory this year?
16. What is your biggest failure this year?
17. What did you like best about what you did this month?
18. Tell me about an accomplishment that really surprised you.
19. How have we helped you become a better manager this year?
21. What do you hope to improve in the coming weeks/months?
What is your superpower?
22. What are you proud of accomplishing this past week?
23. If you were a color, what color would you be and why?
24. Tell me about the best day of your life so far.
25. Pick three words to describe yourself, and one word to describe someone who gets under your skin
26. Who was the last person on earth that texted or called you?   How did they make you feel?
27. When was the last time you asked for help?
28. What is the best thing about working here?
29. Tell me about an average workweek on your team.
30. What is your favorite sports team? Why?
31. If you won $1 million today, what would you do with it?
32. What is your dream vacation and why?
33. Tell me about a time when you went above and beyond to help someone out.
34. What does (Title) mean to you?
35. Think of 3 things that you obsessionally keep up with?
36. What is the most important advice that your mother/father/sister/brother ever gave you?
37. If you had a superpower, what would it be and why?
38. What does the word 'tough' mean to you in real life?
39. Who is the first person that comes to mind when someone mentions your company's name?
40. What do you think is the most important thing to know about managing?
41. What have we done wrong this week that you think might be the best way to correct?
42. What is your favorite quote? Why?
43. What have you learned from reviewing your mistakes in the past year?
44. Do you follow any coaches/mentors/books online or elsewhere and what are they about?
45. If you could change one thing about yourself, what would it be and why?
46. What is your greatest weakness as a manager and how can we help you improve?
47. Tell us how long you have worked at (Company).
48. What is the best thing that happened to you in the last month?
49. What is the best thing that happened to your company in the last month?
50. What has been one of the biggest accomplishments or most rewarding tasks at work this year?
51. Tell me about a time when someone actually listened to your advice.
52. Whose work do you admire and why?
53. Who is the most important figure in your career to date and why?
54. What are the three greatest things you have ever done in your life?
55. What does success look like to you?
56. Who is your favorite entertainer or athlete right now? Why, and how do they make you feel physically, mentally, emotionally, etc.?
57. When you see us in the hallway, what do you think?
58. What would you do if you were the last person on earth?
59. If you could change one thing about your boss, what would it be?
60. What is the most effective way to communicate with your direct report/team?
61. What are we doing really well at this company and what are we not doing as well as we can?
62. What are 3 things that are most important to you professionally?
63. What are 3 things you hope to achieve personally this year?
64. What is the most amazing resource that we have for you?
65. What is a challenge that you are currently facing or will face in the coming weeks, months, or years?
66. If you could go back to school tomorrow and do it all over again, what would you do differently?
67. Who is your favorite entrepreneur and why?
68. Tell me about an "aha" moment in your career so far.
69. Tell me about the prerequisites for your job.
70. What are we not doing that you think would make a difference?
71. How do you feel about our company's (product, service, mission) right now?
72. What has been a significant struggle for you recently?
73. Who is your favorite actor/actress and why?
74. Think back to a time when you felt great at work, what did you do differently that day than other days?
75. What has been the most exciting time in your life/career so far?
76. Who is the best speaker you have seen at a conference or event recently and why are they memorable to you?
77. Tell me about a time when something went wrong on your team and what happened next.

Start Asking Your Own Skip-Level Meeting Questions

As the leader, you’ll be asking most of the questions. But don’t be afraid to relinquish some control so junior-level employees can provide their perspective on what they think is important. 

And don’t feel as if you must ask a completely canned list of questions. Though a partially uniform set of questions can help highlight patterns, some answers may require deeper exploration than others. So keep your mind open and start uncovering your manager’s blind spots at your next skip-level meeting.

What Do You Say In A Skip-Level Meeting?

Here are some examples of good topics to discuss in a skip-level meeting:

  • What is your specific function on the team?
  • Does anyone need a new role or different responsibilities?
  • What types of communication skills could be added to their repertoire?
  • How does your current work in progress compare to what you want it to be?
  • What are the greatest strengths your manager has, and how can you focus on those?
  • What do you feel is his or her greatest weakness and how can help to make it better?
  • How can you work best with your manager to help strengthen the team?
  • How is your communication with your manager? What are some things you would like to change in that regard?
  • Do you understand what's expected of you at work at this level compared to before? If not, how well could your manager explain it if he or she.
  • What are your goals for the next 12 months? Are they in line with the team's goals?

Are Skip-Level Meetings Bad?

In many organizations, skipping the level of management between lower-level employees and higher-level executives is common. Although this may seem like a good idea at first glance, skipping those levels of management can actually have some negative consequences. Here are a few:

  • Choosing not to meet with the manager can have negative effects. If a manager doesn't know about an issue, it can be harder to fix.
  • Even if a decision is made to skip executive-level meetings, skipping the level of managers is still crucial. Let's say that there are no managers in place at your plant or your store. If you and the workers don't know how to solve a problem, there is nothing that can be done to prevent more problems from happening.
  • Skipping levels of management actually may cause lower-level employees to think less of their employers. If lower-level employees see that they aren't meeting with their managers and the higher-ups, they may think that something is wrong with the company or their bosses.
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