Better Meetings

85+ skip-level meeting questions for managers & employees

85+ skip-level meeting questions-featured image

Have you ever wanted to ask your boss’s boss a question? Or find out what your managers are leaving out when reporting on the staff performance? You need something called a skip-level meeting — and you’re about to learn all about it.

Whether you’ll be attending one of these as an employee or as a senior manager, we’ve assembled a list of 85+ questions to get you started.

Table of contents

  • What is a skip-level meeting?

  • What are the benefits of skip-level meetings?

  • Skip-level questions for managers and executives to ask employees

  • Skip-level questions for employees to ask executives and managers

  • Free skip-level meeting agenda template

  • 5 tips to better prepare and run skip-level meetings

What is a skip-level meeting?

A skip-level meeting is a one-on-one meeting where senior-level managers or executives get to connect directly with staff-level employees, bypassing their direct managers. 

Skip-level meetings help leaders get a firsthand insight into what goes on at the ground level of their organization. Additionally, they can get feedback on the performance of managers and suss out if employees are fully engaged in their roles.

What are the benefits of skip-level meetings?

The main purpose of a skip-level meeting is to allow senior managers to gather feedback directly from front-line employees, including individual contributors or junior managers. 

For those employees, the skip-level meeting is a chance to talk to their manager’s managers and both give and receive feedback on certain aspects of their work.

In addition to these two main benefits, skip-level meetings also:

  • Foster positive relationships, transparency, and open communication between people at all levels

  • Help determine the effectiveness of managers 

  • Evaluate employee engagement

  • Help managers become better leaders through feedback 

Effective skip-level meetings need great questions, so take a look at our question list for inspiration.

Skip-level questions for managers and executives to ask employees

At a skip-level meeting, a senior manager or leader can find out a lot about the work environment of lower-level employees, as long as they ask the right questions. 

Pick and choose the questions you need to make your next skip-level meeting a productive one.

Questions to build rapport

It’s a good idea to begin any one-on-one meeting with a quick check-in and a warm-up question. Here are some ideas to help build rapport and open up the conversation: 

  1. What motivates you to do your job?

  2. Where did you go to college? 

  3. What’s a book, movie, TV show, or podcast you’re currently obsessed with?

  4. Are you planning on going on a trip soon? (OR) Have you been on any trips lately?

  5. What do you like to do in your free time? What are your hobbies?

  6. Where did you grow up? 

  7. What's your favorite thing about living in [your city/town/region]?

  8. Who were some of your role models when you began your career?

  9. How did you spend your last weekend?

  10. What’s your dream vacation?

Questions to get manager feedback

High-performing teams need high-performing managers, so a skip-level meeting is a good opportunity to get candid feedback on how managers between levels are performing. 

Here are the questions to help you do that:

  1. Does your manager provide you with the necessary resources to succeed?

  2. How does your manager act under pressure?

  3. How does your manager help you prioritize tasks?

  4. How does your manager motivate your team?

  5.  How does your manager address your team’s needs and concerns?

  6. Do you feel like your manager treats all employees equally?

  7.  What could your manager be doing better?

  8. What is your manager’s greatest strength?

  9. Does your manager foster a psychologically safe environment? Give an example.

  10. How does your manager help you manage your workload and ensure you have enough to do?

  11. What works well in your department right now? (e.g., systems, processes, technology, feedback, etc.)

  12. What needs improvement? Are there obstacles preventing you from being successful? (e.g., technology, top-level support, more feedback, etc.)

  13. What can I and your manager start doing to help you be successful in your role? What can we stop doing?

  14. What one thing does this company need to start doing right away to be more successful?

  15. What one thing does this company need to stop doing right away to be more successful?

  16. What one thing does this company need to continue doing to be successful?

Questions to get team feedback

An effective one-on-one skip meeting should include some questions about how employees are getting along as a team and managing their workflows.

Here are some ideas to get you started:

  1. How collaborative is your team, on a scale of 1 to 10? Explain.

  2. What’s the best thing about working with your team?

  3. Which team project do you think has been a great success recently?

  4. Does your team communicate smoothly with other teams?

  5. What’s the biggest challenge for your team right now?

  6. What do you think your team does well?

  7. What one thing could we do to improve team productivity?

  8. What teamwork process(es) in our organization are you not satisfied with?

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

Questions about employee satisfaction

When employees are satisfied, they’re 31% more productive. Here are some one-on-one meeting questions to help you gauge employee satisfaction: 

  1. What do you enjoy most about your role?

  2. How satisfied are you with your current role and working status?

  3. Do you feel a sense of connection with your coworkers?

  4. Do you feel your current work brings out your full potential?

  5. Do you find your work meaningful?

  6. How would you rate our company’s culture on a scale of 1 to 10 (with 10 being the best)? Explain.

  7. Does our company offer adequate opportunities for you to learn and grow?

  8. How often are you stressed at work?

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

  10. Would you recommend this company to your friends as an employer?

  11. Do you feel excited about coming to work?

  12. What is your least favorite thing about your job?

Questions about employee productivity

With employee productivity and happiness top-of-mind, you’ll probably want to ask some questions about it.

A few suggestions:

  1. What are your top priorities right now? What can we do to help you with this?

  2. Does our company give you the tools and resources to do your job well?

  3. What percentage of your time are you spending in meetings vs. doing deep work?

  4. What would you like to spend more time on?

  5. What would you like to spend less time on?

  6. When do you get your best work done? In the morning,  afternoon, or evening?

  7. How do you like to organize your workday?

  8. What are your biggest time wasters each day and week?

  9. How could we help you be more productive?

  10. Are there any software, tools, or resources that you think you could benefit from?

Skip-level questions for employees to ask high-level executives

If you’ve been invited to a skip-level meeting with your boss’s boss, it’s natural to feel anxious. After all, you’ll have the opportunity for some face time with someone in a leadership position. 

It’s always a good idea to come prepared, so here’s what you can ask when it’s your turn to pose questions to the leadership.

Questions about strategy

Here are questions you can ask to get some feedback on the strategies your team or department is using.

  1. What direction do you see the company going in the next  12-24  months?

  2. Does our team support the company's mission? If not, what changes are needed?

  3. Which of our team’s strategies/projects do you feel have been most effective?

  4. Which of our team’s strategies/projects do you feel have been the least effective?

  5. How do you see our team growing in the next 6-12 months, given the company goals?

  6. Do you think our team is using its resources well?

  7. What other resources/processes do you think our team should implement to have more effective strategies?

Questions to gain feedback

Asking for feedback is an important skill if you want to get ahead in your career. Here are some questions that will help you with that:

  1. What questions can I ask my manager to receive the best feedback?

  2. What kind of feedback is most effective to give to my manager?

  3. How often should I be asking for feedback from my manager?

  4. How often should I give feedback to my manager?

  5. Can you give me some feedback on [the last project your team did]?

  6. How can I give feedback to upper management?

  7. How can I ask for feedback from upper management?

  8. How can our team improve its performance?

  9. What do you think was the most successful of all the projects our team completed in the last [quarter/year]? Why?

Questions regarding career development

Speaking to senior leaders of your company is a good chance to get some useful tips and insight for your career development. After all, these are people who succeeded, so why not learn from them?

Here’s what you can ask:

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

  2. What has your career path been 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 hiring leaders, what specific skills or character traits do you look for?

  6. What career advancement opportunities are available to me in the next 12-24 months?

  7. Are my career goals reasonable? (Note: You’ll likely have to outline your career goals briefly first if the manager doesn’t have visibility into them)

  8. What do I need to improve to take the next step in my career?

  9. Who in this company can I learn the most from?

Questions about alignment

Outside of skip-level meetings, it’s managers who relay strategy and feedback to their direct reports. That means that, unintentionally, what upper management thinks about performance and alignment can get watered down. 

Ask these questions to get info straight from the source:

  1. What projects would you like our team to prioritize this [quarter/year]?

  2. What do you want our team to achieve this [quarter/year]?

  3. Does our team reflect the company's values?

  4. What is the most important thing our team can do this [quarter/year]?

  5. What can our team improve to better achieve company goals?

  6. How can our team better work with other teams to achieve shared goals?

  7. Can you suggest ways I can stretch beyond my role to learn new skills?

Skip-level meeting agenda template

Every effective meeting starts with a good meeting agenda. Sharing an agenda ahead of time helps keep everyone on track and gives meeting participants time to prepare. It’s just good meeting culture!

That’s especially important for a skip-level meeting, since more junior employees may not have had a lot of contact with people in leadership positions. A thoughtful meeting agenda can go a long way to allay some of the anxiety they might feel. Check out our template!

Skip-level meeting template

Of course, a list of questions and an agenda are not everything you need for a good skip-level meeting. That’s why we’ve included some tips in the next section.

5 tips to better prepare and run skip-level meetings

The best skip-level meetings start with careful preparation and proceed with friendliness and openness. 

To help you with that, here are some tips to make sure your next skip-level meeting is a productive one. 

1. Create a meeting agenda

You might be wondering why we’ve mentioned agendas several times already. No, it’s not just because Vowel has a nifty meeting agenda feature with lots of templates to make creating one easy. 

Vowel meeting agenda

It’s because a meeting agenda is the difference between a meeting that’s orderly and productive and one that quickly loses focus. Sending out a meeting agenda alongside the invite communicates that you’re coming prepared and expect the same from other attendees. 

2. Have your questions ready

Don’t get caught off guard when the meeting starts. Have all your questions ready beforehand to provide a roadmap for the conversation and make the most of your time. 

You can make a pool of specific questions based on what you want to discuss. If you’re running a series of skip-level meetings, you can turn the questions into a template for quick reference and easy sharing.

Tip: Start with your highest priority 5-8 questions for 30-45 minute meetings. You don’t want to crowd the schedule! 

3. Be honest

Remember: the objective of the skip-level meeting is to get real and actionable feedback. The kind of feedback that the traditional hierarchical structure of a company can obscure and make inaccessible. Because of that, both parties must be as open as possible. 

It’s natural for employees to feel apprehensive and nervous when talking with leaders. So, it’s up to the senior person in the meeting to be the facilitator of open and honest communication. 

Encourage team members to be open by making them feel comfortable and respected.

4. Take notes

It would be a shame for all the direct feedback and actionable takeaways that come out of skip-level meetings to be lost. 

The usual solution is to keep meeting notes and minutes. Having a record of the meeting lets you get the most out of the feedback you receive because you can easily revisit it. You can even improve future meetings by analyzing the effectiveness of previous ones. 

With Vowel, creating meeting notes is straightforward. You can take collaborative notes during the meeting and have the whole meeting recorded and transcribed, too. 

Post-meeting view with transcript

That way, all your skip-level meetings can become one searchable knowledge base with time-stamped notes and transcripts.

5. Handle manager feedback the right way

During the meeting, an employee might share an unsolicited thought or concern about their manager. 

Acting on that kind of feedback can be tough. You’ll want to do it in a way that doesn’t add tension in your organization but still shows the employee that you took the concern and complaint seriously. 

If the concern involves a conflict that the employee and manager can resolve between themselves, then instruct the employee on how to proceed. That way you’ll be respecting the authority of the manager.

Have more impactful meetings with the right tool

Skip-level meetings, when done properly, are an invaluable tool for senior leaders to connect with front-line employees and get their honest feedback. 

The right meeting tool can go a long way to make your meetings more impactful and useful, even after they happen. Vowel lets you host video meetings, but that’s just the beginning: there’s live transcription, instant recordings, bookmarks, clips, collaborative notes and agendas, meeting recaps, and more. And it’s all in one place, so there’s no need for third-party add-ons or extra cloud storage. 

If you’re ready to try it out, all you need to do is sign up now for free!

FAQs

Q1. How long should a skip-level meeting be?

As a rule of thumb, you want your skip-level meetings to last between 30 and 60 minutes based on the number of questions and topics you wish to cover. 

The skip-level one-on-one meeting should not be so long as to make the lower-level employees feel like they’re being interrogated. 

Q2. How often should skip-level meetings happen?

You should hold skip-level meetings at least once quarterly. If you feel it’s beneficial, you can choose to hold them more often but this is likely to be affected by the number of skips you need to hold based on the size of your team.

Q3. Are skip-level meetings bad?

When held properly and with the right intentions, skip-level meetings are great. They let senior leaders share strategy with lower-level employees and connect with people they’d have little contact with otherwise.

Just make sure it’s made clear that the skip meeting is not the time to get feedback from the employee’s direct supervisor. The direct manager needs to share that with the employee in a different one-on-one.