Skip-level meetings questions to ask as icebreakers
Start your skip-level meeting by asking fun questions. In general, icebreakers are great at improving staff communication, and in the case of skip-level meetings, icebreakers are extremely important to get the conversation flowing. It can be nerve-wracking for an employee to meet with their manager’s supervisor, so asking a few rapport-building, softball questions is crucial to calming employees’ nerves and getting them to speak openly. Here are some fun questions you can begin with:
- What are some of your hobbies?
- What is your idea of a dream vacation?
- What is the first trip you remember taking with your family?
- Who is your favorite singer or band?
- What is the most recent concert you went to?
- What is the best streaming TV show you watched recently?
- What was the best day of the last year for you personally?
- What is your favorite quote?
- When was a time in your life that you laughed the hardest at something?
- Who is someone you look up to in our industry (but outside our company)?
- What podcast do you listen to regularly that you’d recommend to your coworkers?
- What is the number one thing that motivates you to do your job well?
- What is your greatest non-work achievement within the past year or so?
While it’s fun to talk about topics like favorite streaming shows and podcasts, the point of these questions is to break the ice before getting into more pertinent questions. So ask as many of the above questions as you feel you need to before moving on, but don’t get too carried away with them.
Skip-level meetings questions to ask for team feedback
After you have made the employee comfortable via a few icebreaker questions, it’s time to begin gathering more pertinent information about how they and their team are functioning. These questions will help you determine how the employee feels about their own role, how that fits into their team’s work and how the employee feels about the company at large.
Note that none of the following are yes or no questions, as they won’t yield much value. You want the employee to speak freely and expound upon their points, so the skip-level meeting should have the feel of a free-flowing, open-ended conversation.
14. What is working well in your department right now?
15. What one thing should your team implement immediately to be more successful?
16. What one thing should your team stop doing immediately to be more successful?
17. What do you think is the best part about your team?
18. How well do you feel your team functions within the larger company?
19. Who on your team would you say picks up extra slack, and are they recognized for doing so by team leadership and company leadership?
20. How do you feel about your team’s support of our company mission?
21. If you were allowed to add more head count to your team, what sort of person would you want to see hired to make your job and the team’s job go more smoothly? Or would it require adding more than one person to the team?
22. What is the most recent example of your team doing a project exceptionally well?
23. What is the most recent example of your team failing to live up to its potential on a project?
24. What is your favorite thing about working with the people you work with?
25. Do you feel the workload required of your team is too light, just about right or too great?
26. Do you feel your own workload is too light, just about right or too great?
27. Without naming names, do you feel members of your team are underperforming, and if so, how does that affect your workload?
28. If your friend saw an opening here and asked you to describe the quality of our company’s work, how would you answer?
29. If the same friend asked you to describe the company culture to see if it was a good fit, how would you answer?
Skip-level meetings questions to ask for individual feedback
While the above section largely deals with how the employee feels about their team and the company, these questions focus more on the employee’s own sense of their role in the company, as well as their larger career goals.
30. What obstacles are preventing you from being successful in your team and within the larger company?
31. What resources do you feel you’re not getting from your manager in order for you to be personally successful in your role?
32. On a daily basis, what causes the biggest bottleneck in your workflow? What about on a less frequent basis (weekly or monthly)?
33. Who on your team has acted as a mentor to you?
34. Are you happy with your current level of compensation and the company’s benefits policy? What would you change about our benefits?
35. If you could choose between staying on your current team and moving to another team here, which would you choose and why?
36. Tell me about a recent day working here when you went home at night feeling a great sense of accomplishment.
37. What could the company be doing better to leverage your skills? Do you have “secret skills” that aren’t necessarily part of your regular job description but that you think could be useful to the company in some way?
38. On a scale of one to 10, how happy do you feel about coming to work every day?
39. Tell me about a recent day here when you went home from work feeling that things hadn’t gone quite how you wanted them to.
40. What was your position when you were hired at our company, and how many years did it take you to work your way up to your current role?
41. What goals do you have on a monthly basis in your role? What about on a longer-term basis?
42. Do you feel there is a chance for you to advance in this company, or do you think you have achieved the highest position you can attain here?
43. If you could choose any role in this company to fill, would you keep your current position or move into another role in your team?
44. If you could rewrite your job description, what would you add, delete or otherwise change?
45. What has surprised you most since you started working here?
Skip-level meetings questions to ask for manager feedback
One of the most important aspects of holding a skip-level meeting is discovering how lower-level employees feel about their boss — that is, how they feel about your direct report — and whether the team has any management problems or potential red flags that need to be addressed.
In most cases, your direct report isn’t going to willingly tell you if the team has issues with their performance or management style, nor will they report themselves for acting as an absent manager. That’s why it’s critical to hear directly from the team without the manager being present. These questions will help you gather key information on how the employee and team feel about their boss:
46. Are you getting the right amount of feedback from your manager?
47. Do you consider your boss to be a micromanager, and if so, how does this affect you?
48. How does your manager act when there is a crisis at work?
49. What does your manager do to encourage your team?
50. Does your manager address your team’s needs and concerns?
51. What obstacles are you facing that you don’t believe your manager is addressing?
52. On a scale of one to 10, how well would you say your manager supports you and your work? Why did you choose the score you did?
53. Have you ever experienced a situation in which you didn’t fully trust what your manager was saying?
54. Has there ever been a situation in which you don’t feel your manager acted ethically, and what did you do about the situation?
55. When was the last time you asked your manager for help, and did you receive it?
56. When was the last time you felt that your manager did a great job on a project?
57. When was the last time your manager did a great job in dealing with a personnel issue?
58. Fill in the blank: The best part of working with my manager is ____, and the worst part is ____.
59. What is your manager’s greatest strength, and what is their greatest weakness?
60. Do you feel comfortable approaching your manager when issues arise, and if not, why not?
61. How often does your manager tell you that you’re doing a good job?
62. How often does your manager speak critically of your work, and is it ever in front of other team members?
63. If you were suddenly made team manager, what are some of the first steps you’d take to change or improve things?
64. Is there someone on your team who you think would be a better team leader than your current manager, and why?
65. When your manager is out of the office for personal reasons or traveling for work, does your work day change considerably? Does the mood of the team change?
66. Does your manager treat everyone on your team equally, and if not, can you think of an example where your manager didn’t live up to that?
Skip-level meetings questions to ask during a company crisis
During a time of crisis for a business — economic uncertainty, a downturn in the industry or amid layoffs — employees will look to company leadership to get a sense of how the company is faring. However, it can be just as important for leadership to examine staff morale during a crisis to ensure that its staff isn’t unhappy — or worse — heading for the exits.
That’s why a time of company crisis is a critical juncture for holding skip-level meetings. You can ask several of the following questions during any skip-level meeting, but they’re especially relevant during a time of choppy waters for your business.
67. How is the morale in your team?
68. How do you feel about the morale of the company at large?
69. Do you sense that employees are starting to look for other places to work?
70. What is your biggest concern now regarding our company?
71. How secure do you feel that your role here is safe?
72. If you were with a friend having a cup of coffee, and they asked you how things are going at our company, how would you describe the situation to them?
73. What specific actions do you think your team and our company can be taking to weather this storm?
74. How have recent layoffs here impacted your opinion of our company, and do you think we handled the need for layoffs properly and fairly?
75. When you look at our competitors during this uncertain time, can you point to anything they’re doing that you think we should also be doing? What are they?
76. If you were made the head of the company now, what action or actions would you take to help us weather this downturn?
77. Do you feel confident about the future of our company?
The importance of skip-level meetings for your company
By exposing yourself to voices in the company that you don’t always hear on a daily or even monthly basis, skip-level meetings are among the best ways to take the temperature of your staff.
Making these meetings a regular part of how your company operates — and asking the right skip-level meeting questions — will help you to better understand your company’s operations and improve them.
