90+ Best Skip-Level Meeting Questions to Prepare! (+ Free Template)

Are you a senior leader at an organization and feeling out of touch with the rank and file? Or are you an employee who is asked to have a one-on-one meeting with your manager’s boss and worried about what to say?

‍If you answered ‘yes’ to those questions, don't worry! Skip-level one-on-one meetings are a common thing in modern organizations to improve communication and information flow. 

In this article, we’ll explain what a skip-level meeting is and list 90+ skip-level questions to ask. Now, let’s get started. 

What Is a Skip-level Meeting?

The skip-level meeting, as the name suggests, is a one-on-one meeting where a senior manager connects directly with an employee, skipping the employee’s direct manager.

There is often a gap between direct reports supervised by managers and the senior leaders to whom these managers answer. Skip-level meetings are a remedy to that situation.

‍By having one-on-one interactions:

• Leaders can get first-hand insights into what goes on at the grassroots level of the organization, get feedback about the managers and the company, and determine if employees are enjoying their roles.

• Employees are able to share their feedback, know more about company strategies, and even leave a good impression.

‍If you are going to have such meetings and are clueless about what to ask in a skip-level meeting, keep reading on. 

This post has highlighted the best skip-level meeting questions to ask your team as a senior leader. Since skip-level meetings are a two-way interaction, I have also underlined questions that direct reports can ask senior leaders. 

60 Questions to Ask Employees at a Skip-level Meeting

Asking the right questions makes your skip-level meetings more effective. 

Remember, your aim of the skip-level meetings as an upper manager is to build trust, gain feedback, and learn where there is dysfunction. So the questions should also be crafted neatly and around these topics.

A small tip:  lay out questions you’d like to ask your employees beforehand; don’t wait until you call them into your office.

Questions to build rapport and trust

You would agree that having a meeting with a leader can make an employee a little anxious. As a senior leader, it behooves you to reduce the tension in the room.    

How do you do that? By asking ice-breaker questions at the start of the meeting to build rapport and a level of trust. These questions should be personal and unrelated to their role and the organization. It’s a way to show the employee that you’re human too and that you’re interested in their life beyond work. 

Here are questions you can use to build rapport as you kick off the meeting:

1. Where did you grow up? Where did you go to college?

2. Where do you live? How long it takes for you to arrive at the office?

3. What do you like to do outside of work?

4. How did you spend your last weekend?

5. What’s your dream vacation?

6. What would you do if you won the lottery?

7. What’s your favorite song at the moment? Who’s your favorite singer?

8. Are you a fan of any sports team?

9. Will you recommend to me a book/TV series/movie that you’ve watched recently?

10. What’s your favorite festive holiday, and why?

11. What made you decide to become [role]?

12. If they have any kids, spouses, or siblings, you can ask: How are your kids? How is your spouse? How is/are your sibling(s)?

Be careful not to get carried away and spend too much time building rapport. It’s just a precursor to the main questions about feedback and performance. Regardless, take this section seriously. Establishing personal connections with your employees is an effective team management technique.

Questions to get manager feedback

“Feedback is the breakfast of champions.” - Ken Blanchard, Ph.D., management expert and best–selling author.

‍Because senior leaders are somehow far from the action, it would be difficult for you to get wind of what goes on between managers and direct reports and the general perception of the work environment. 

Skip-level meetings come to the rescue! Below are some questions you can use to derive feedback about the manager’s performance.

13. What’s the best part of working with your manager?

14. What’s the hardest part of working with your manager?

15. What is a recent situation you feel like your manager did a great job?

16. Which recent project do you wish your manager handled effectively?

17. Do you feel your manager is approachable?

18. Do you trust your manager at work? Why/why not?

19. What’s your manager’s biggest strength?

20. Do you think you are getting enough feedback from your manager?

21. How would you describe your manager’s communication style? Do you like it?

22. If you were managing the team, what’s one thing you would do differently?

Questions to gain team feedback

What’s a skip-level meeting without getting feedback on teamwork and the work atmosphere? In fact, gaining feedback is one of the primary purposes of skip-level meetings.

Finding out how the team as a whole is doing can get more insights and help improve team productivity.

 23. Does our company give your team the tools and resources to do the job well?

24. Do you think there is enough collaboration within your team?

25. What’s the best thing about working on your team? 

26. Which team project do you think is a great success recently?

27. Does your team communicate smoothly with other teams?

28. What’s the biggest challenge your team faces?

29. What part do you think your team does really well?

30. What’s one thing we could do to improve team productivity?

31. Do you feel your team is overworked or underworked?

32. What teamwork process(es) in our organization are you less satisfied with?

33. Which team member do you enjoy working with the most? Why?

Questions about employee satisfaction

It’s widely known that when employees are satisfied with their jobs, they’re much more likely to be happy and productive, and the employee retention rate will be higher. 

Gauging employee satisfaction and offering help is also one important talking point in a skip-level meeting.

34. What do you enjoy most about your role?

35. Are you satisfied with your current role and working status?

36. Are you proud of being part of the organization?

37. Do you feel connected to your co-workers?

38. Do you feel the current work brings out your potential?

39. Do you find the work meaningful?

40. Do you like our company’s culture?

41. Does our company offer adequate opportunities for you to grow up?

42. How often do you feel stressed at work?

43. What’s the most challenging part of your job?

44. What’s your least favorite thing about your job?

Questions about career development

It’s only when a company and the leader care about the employee’s personal development, will an employee feels connected.

Below are some career growth questions to ask at a skip-level meeting.

45. Where do you see yourself within the team in the next year?

46. What is your dream job?

47. What are your strengths while doing your job?

48. If you were given a second chance, would you choose the current profession again?

49. Who do you look up to for inspiration?

50. What are your career interests?

51. What are your long-term career goals (5 years)?

52. What skills would you need to achieve your goals?

53. Are you pursuing any learning opportunities in the company?

54. What career accomplishment are you most proud of?

55. Do you think the staff promotion system in the organization is fair?

Questions about company growth

At the end of the skip-level meeting, don’t forget to take some time to talk about the company and let employees feel that their opinions are valued. However, don’t ask too general questions like industry change, make them personal.

56. What do you think is the biggest challenge the company faces?

57. What are the advantages you think our company has?

58. What’s your opinion about the industry we are in?

59. What’s one thing you think the company should do right away?

60. Do you think our company is going the correct way?

32 Skip-level Meeting Questions to Ask Your Boss’s Boss

You’ve been informed that you have a skip-level meeting with a senior leader at your organization. Although your leader will ask most of the questions, you don’t want to go into the meeting without having your own thoughts. 

‍Having questions of your own shows that you prepared for the meeting and are committed to learning.  Here’s what to ask in a skip-level meeting as an employee.

Career

1. What’s your biggest challenge as a leader?

2. What’s your career path like? 

3. How long did it take you to get to your current position?

4. What traits do you value most in leaders? 

5. When appointing leaders, what specific skill(s) or character traits do you look out for?

6. What career advancement opportunities are available to me in this organization?

7. Are my career goals reasonable?

8. Do you value team projects or independent projects more?

9. What areas should I improve to take a big step in my career?

10. Who in the company can I learn the most from?

Feedback

11. What do you think about our team’s performance?

12. What do you wish we did better as a team?

13. Do you have any feedback on the {last project} our team finished?

14. Which project do you think was the most successful one that all teams completed in the last quarter? Why?

15. How can I give feedback to upper management?

16. What do you suggest we do to be more productive?

17. Are you satisfied with our team’s performance currently?

18. What’s one thing we can learn from other teams?

19. What skills do you think our team is lacking?

Alignment

20. What do you want our team to achieve this quarter/year?

21. Does our team embed company values?

22. How can our team work with other teams to achieve common goals?

23. Does this team support the company's mission?

24. What do you suggest our team prioritize in this quarter?

25. How can our team better contribute to the organization?

26. Does our team align with the company goals?

27. Do other teams have similar goals to ours?

Company Strategy

28. Where do you see this organization in the next few years?

29. What’s the company’s ultimate goal?

30. What factors to consider while creating company development strategies?

31. What strategies do you think are most effective?

32. Do you completely agree with the strategies we are taking?

Tips to Make the Most of Skip-level Meetings

Whether you’re the leader or the employee, both aim to create a positive outcome from the meetings. Now you know what questions to ask at a skip-level meeting, you should also learn some tips to conduct more successful conversations.

Be open and honest

Since the meeting is all about getting real feedback, both parties should maintain an honest attitude. 

It’s natural for employees to get nervous while meeting with leaders and are afraid to share their ideas freely. Therefore, leaders should take responsibility for guiding team members and encouraging them. 

Meet with everyone

I know, it seems like an arduous task. But consider it the price you pay for keeping your team together.

Once you start these, it's important to ensure you don't miss anyone as other employees may also want to meet with you. Otherwise, it may give off a sense of favoritism within the organization, and employees whom you have not met may feel slighted. Another reason is that you don’t want to look like you're playing politics with certain people.

Handle feedback properly

Employees tend to share their concerns about their managers during skip-level meetings, some of which may be unsolicited. How you act on this feedback is important. Be careful not to act in a way that may heighten tension within the organization. 

‍At the same time, you must take action. Try to do something about the concern so that the employee won’t think you don’t regard their complaint. 

If the concern is about a conflict that can be resolved by the manager and employee without you interrupting, direct the employee on what to do. That way, you’re respecting the authority of the manager.

Free Skip-level Meeting Agenda Template

Hosting skip-level meetings is a great way to check in on current team members and helps uncover issues that upper managers may not see by themselves.

We have also prepared a template to get you started immediately. You may copy it and make changes as you see fit.

Check-In 

A quick check-in with the employee to break the ice.

• How are you feeling in your current role?

About the Company

Discuss the company's growth, future development, and potential challenges.

• Where do you see the company headed in the next few years?

• What’s the biggest challenge facing the organization?

Feedback

Listen to employees’ feedback about the company, the team, and their manager.

• How is the team performing from your perspective?

• What’s the best part of working with your team or <your manager>?

• What’s one thing we should start, continue, or stop doing as a team?

Employee Growth

Know more about the employee and see how to help him grow with the organization.

• Is anything blocking/bothering you in your daily work?

• What can your manager or I do to better support you?

• What do you wish to accomplish in the company next?

Action Items

What are your next steps after this discussion?

• Action 1