15 Skip-level Meeting Questions (For Managers and Employees) 2024
Meetings Project Management

15 Skip-level Meeting Questions (For Managers and Employees) 2024

Ayush Kudesia
Ayush Kudesia

Feeling tongue-tied in a skip-level meeting? Don't worry. We've all been there. These meetings can be tricky, but they can be super valuable with the right approach.

In this article, we'll discuss everything from a skip-level meeting and its importance to the ten most important skip-level meeting questions to ask (as managers and employees).

So, let’s get right into it.

In this blog, we will cover:

  • What is a skip-level meeting?
  • Who decides the agenda of the skip-level meeting?
  • Importance of skip-level meetings
  • How to prepare for a skip-level meeting as an employee
  • Skip-level meeting agenda template for employees
  • 10 skip-level meeting questions to ask managers
  • How to prepare for a skip-level meeting as a manager
  • Skip-level meeting agenda template for managers
  • 10 skip-level meeting questions to ask employees
  • Bonus skip-level meeting questions

What is a skip-level meeting?

What is a skip-level meeting?
Source: Freepik

Skip-level meetings bring employees face-to-face directly with someone a few levels above you. These meetings are called ‘skip-level’ because you skip your immediate supervisor/manager and directly converse with people higher up the hierarchy.

These are relatively short meetings aimed at building transparent communication across all levels. This is a platform to discuss the company’s growth and your own. You can also discuss strategic changes in your organization and share feedback.

Whether you're looking to build relationships, gather information, or make a positive impression, these meetings are important for employees and managers.

Who decides the agenda of the skip-level meeting?

A comprehensive and relevant meeting agenda is crucial for a productive and efficient meeting, and skip-level meetings are no different.

Usually, the manager prepares an agenda tailored to the company’s current goals. But it’s best to create it with employees to make these meetings more inclusive and transparent.

Duration: These meetings usually last 30-45 minutes and happen bi-monthly or monthly.

Importance of skip-level meetings

It is not every day that employees get to interact with senior management. A skip-level meeting facilitates candid interactions and builds a culture of open communication and problem-solving without the usual hierarchy getting in the way.

They're important because:

  • It gives employees a platform to discuss new ideas and concerns.
  • Employees get to know their senior management, how they work, and their management style.
  • It makes employees feel confident that the senior management is approachable. They feel valued and heard.
  • Employees get a better understanding of the company’s goals and strategy.
  • It results in better decision-making as managers understand their team’s perspective.
  • It makes the organization much more transparent for both employees and managers.

Managers benefit from these meetings by better understanding employee satisfaction. They learn how their team works and what issues persist that they previously weren’t aware of. This knowledge helps them realign the company goals accordingly with the employees’ immediate managers.

It also gives managers a forum to appreciate and recognize their employees' work directly.

How to prepare for a skip-level meeting as an employee

How to prepare for a skip-level meeting as an employee
Source: Freepik

Whether it is your first skip-level meeting or otherwise, it’s best to always prepare for it. Think of some good skip-level questions and your career aspirations before diving into the conversation. Here’s how employees can approach their preparation:

  • Get to know your boss’s boss: The invite you received has the names of all the attendees from the senior management. Research them. Review their profiles and roles to familiarize yourself with them. It will give you some ideas about topics you can discuss.
  • Make clear objectives: Be clear about what you hope to gain from this meeting. You might have some concerns or ideas to share. Prepare your talking points to avoid missing out on anything.
  • Show respect: This goes without saying. Respect everyone in the meeting. Take any feedback or criticism you get with an open mind. Implement it, as it will only help your personal growth.
  • Don’t be late: It doesn’t matter if this meeting takes place online or offline; be on time. Also, dress professionally and be confident.

Prepare an agenda with questions to ask at a skip-level meeting. Here is an example to get you started.

Skip-level meeting agenda template for employees

💡 Skip-level meeting agenda template

1. Introduction (2 min)
  • Introduce yourself and what your current responsibilities are in the organization.
  • Share something you enjoy outside of work. Break the ice a little.

  • 2. Share progress updates (5 min)
  • Share the current timeline of your projects and whether your team is on track to complete the project on time.
  • Ask for any team-specific feedback or suggestions.

  • 3. Discuss your personal goals (5 min)
  • Share your personal and professional goals for the next 12 months. Want to get certified to do your job better? Ask for it here.
  • Ask for any support or resources needed to achieve them.

  • 4. Share feedback on the company work culture (5 min)
  • Share suggestions for improving the work culture and team efficiency.
  • Ask for any specific changes that could make your job more effective
  • .

    5. Discuss the current company strategy (5 min)
  • Give feedback on how effective you think the current company strategy is.
  • Discuss what changes can be made to make the work more productive.

  • 6. Open forum (20 min)
  • Expect follow-up questions and responses. This is the place to understand your management’s perspective and dive deeper into areas of your interest.

  • 7. Conclusion (3 mins)
  • Share one takeaway from the meeting.
  • Discuss any next steps or follow-up actions.
  • 15 skip-level meeting questions to ask managers

    Now that you have a skip-level meeting agenda template, here are 10 questions to give you an idea about how you can tailor your questions according to the agenda:

    1. What do the company’s current goals, objectives, and strategies look like?
    2. How close are we to achieving these goals?
    3. How can I contribute more toward these goals?
    4. Are there any challenges I need to be aware of related to my work area?
    5. Are there any areas I can personally contribute to with my current skills?
    6. What can we do to work better as a team?
    7. How can we improve the entire communication of the company?
    8. What new skills do I need to learn to perform my responsibilities better?
    9. What, according to you, is my biggest weakness and my biggest strength?
    10. Are there any major changes happening in the company in the upcoming quarter?
    11. What are the biggest opportunities for innovation in our team/department?
    12. How can we better recognize and celebrate successes within the team?
    13. How can we improve work-life balance for the team?
    14. What are some ways I can get involved in cross-functional projects?
    15. Is there anything I can do to help you be more successful in your role?

    How to prepare for a skip-level meeting as a manager

    How to prepare for a skip-level meeting as a manager
    Source: Freepik

    If you are a manager preparing for a skip-level meeting, ensure the meeting is a success. You can start by identifying the purpose of the meeting. It will not only help you create a clear agenda but also help you guide the session forward.

    Here’s how you can approach this meeting:

    • Get to know your employees: You can only create an agenda after knowing your employees. You should know their roles and responsibilities and the areas where they excel. This will help you communicate with them in a better way.
    • Create an agenda: Your meeting agenda should include everything you want to discuss/ask with your employees, with a clear goal in mind. Communicate it with the team before the meeting so they also get enough time to prepare.
    • Promote open communication: Many employees might feel intimidated by your seniority and feel uncomfortable presenting their issues. It’s your responsibility to make your team feel at ease. You want them to open up with you without hesitation.
    • Listen carefully: When your team shares their feedback, issues, or concerns over the current working situation, just listen. Encourage them to be open, even if they feel that their issues are trivial. Refrain from countering what they have to say; instead, look for a viable solution to their problem.
    💡 Fireflies Tip

    Fireflies helps build active listening skills with its conversation intelligence platform. If you have skip-level meetings online, use it to see your talk-to-listen ratio, how many words you speak per minute, or the overall sentiment of your call.

    Ready to get started with us? Try Fireflies for free!

    As a manager, you should also prepare an agenda and a list of skip-level questions to ask during the meeting.

    Skip-level meeting agenda template for managers

    💡 Skip-level meeting agenda template

    Introduction (2 min)
  • Introduce yourself and what projects and areas currently fall under your umbrella of work
  • Ask some questions outside the work from your employee to break the ice. Here are some virtual icebreaker ideas if your meeting happens online.

  • 2. Take progress updates (5 min)
  • Ask them about the current progress of the ongoing projects and how the team is doing with respect to the decided timeline.
  • Ask them if they need help with the project and whether it can be done on time.

  • 3. Share any new company updates and changes happening (5 min)
  • Share any proposed/ongoing management changes that are relevant to the employees.
  • Ask them what changes they expect in the company to improve the overall work environment.

  • 4. Discuss the company’s work culture (5 min)
  • Ask them how they feel about the company’s current state and if they are getting appropriate support from their teammates and managers.
  • Ask them how they feel about their current work-life balance.
  • .

    5. Ask them what you can do to help them (5 min)
  • Ask them if they are facing any issues with their managers or team members.
  • Discuss the areas where you can help them resolve their issues.

  • 6. Open forum (20 min)
  • Ask them if they have more questions to ask or if they have something else to discuss.
  • Ask your questions, and analyze their answers to get a better understanding of everything that is going on.

  • 7. Conclusion (3 mins)
  • Share one takeaway from the meeting.
  • Discuss any next steps or follow-up actions.
  • 15 skip-level meeting questions to ask employees

    As a manager, you also need to ask the right questions to get the most information from your employees. Here are some questions that can help you frame your own:

    1. Do you have proper support from your immediate managers and team members? If not, what can we do to improve it?
    2. Can the current company goals be achieved in time? If you need more time or resources, let us know.
    3. Are you comfortable with your work and current projects?
    4. Would you like to pursue new responsibilities beyond your current field?
    5. How would you rate your communication with your team members and management out of 10?
    6. Do you have any suggestions we can implement to improve organization-wide communication?
    7. If you face any issues with your immediate managers, please feel free to bring them forward.
    8. Do you feel satisfied and valued within the company?
    9. Do you have a proper work-life balance?
    10. Does this job provide you with a flexible work culture that you are comfortable with?
    11. What is one thing we, as a company, could do to improve innovation and creativity within your team?
    12. Thinking about the future of our industry, what emerging trends or skills do you think we should be focusing on?
    13. If you could change one thing about our company culture, what would it be?
    14. Do you feel empowered to make decisions within your role? If not, what can we do to improve this?
    15. Is there anything impeding your ability to collaborate effectively with other teams or departments? 

    Please remember that these questions are only to give you an idea. The questions you ask should be tailored to the agenda of your skip-level meeting, considering the nature and scope of your work.

    Bonus skip-level meeting questions

    Here are some other examples of what to ask in skip-level meetings:

    1. Are there any employees that you are impressed with?
    2. Do you have any issues you had voiced before that the management didn’t address?
    3. Would you like to share any issues beyond work affecting your efficiency to work properly?
    4. Have you ever felt unsupported by your fellow team members?
    5. What additional skills do you want to learn?

    Fireflies AI for effective skip-level meetings

    Skip-level meetings offer a unique opportunity to bridge the leadership-employee gap, but virtual settings demand a new strategy. Juggling note-taking, focusing on the conversation, and ensuring everyone's on the same page can feel overwhelming. That's where Fireflies AI comes in.

    Fireflies is more than just a meeting recorder. It's your intelligent assistant that captures every detail, provides actionable insights, and keeps everyone aligned.

    Here's how Fireflies empowers you to have impactful skip-level meetings:

    • Crystal clear communication: Fireflies boasts over 90% accuracy in transcribing meetings across 60+ languages and three English accents (UK, Australian, US). This ensures you don't miss a single point during your discussion.
    • Actionable insights at your fingertips: Fireflies AI goes beyond simply recording the conversation. It generates comprehensive summaries, complete with clear action items and customizable notes.
    • Find what matters fast: Skip-level meetings can cover a lot of ground. Fireflies' Smart Search feature uses AI filters like date, time, questions, and metrics to help you pinpoint crucial information. Track topics to easily review discussions relevant to specific projects or goals.
    • Go beyond words: Understand meeting dynamics with Conversation Intelligence. Gain insights like speaker talk time and sentiment analysis. Analyze speaker participation and sentiment to gauge engagement and identify areas for improvement for more productive exchanges.
    • Boost efficiency with AI assistance: Leverage the power of GPT-4 with AskFred, your virtual assistant within Fireflies. It can answer post-meeting questions about the discussion and even generate follow-up emails to streamline communication and ensure everyone is aligned.
    • Streamline your workflow: Fireflies integrates seamlessly with 40+ popular apps, including your CRM and project management platforms. This allows you to automatically assign action items, log data into CRM tools, and track progress.
    Transform Your Skip-Level Meetings with Fireflies

    Fireflies captures notes & insights in skip-level meetings, letting you focus on the conversation and gain valuable feedback.

    Try Fireflies for free!


    1. What not to do in a skip level meeting?

    Here are some things to avoid during a skip-level meeting:

    • Complain directly about your manager: This is not the forum for airing grievances. Focus on broader issues or roadblocks you're facing.
    • Dominate the conversation: Let everyone have a chance to speak, especially your colleagues.
    • Be unprepared: Review the agenda beforehand and come ready to contribute your thoughts and insights.
    • Focus on trivial matters: Use this opportunity to discuss important issues that impact your work or the company as a whole.
    • Make work-related decisions: Skip-level meetings are for information gathering and open communication, not decision-making.

    2. How do I talk to my skip-level manager?

    Here are some tips for talking to your skip-level manager:

    • Be professional and respectful: Maintain a professional demeanor throughout the conversation.
    • Focus on the big picture: Discuss broader issues and challenges you're facing rather than getting bogged down in daily tasks.
    • Come prepared with talking points: Have specific questions or topics you'd like to discuss in mind.
    • Be clear and concise: Get straight to the point and avoid rambling.
    • Be open to feedback: This is an opportunity to learn and grow, so be receptive to your manager's insights.

    3. What do you write in a skip-level meeting invite?

    Here's what to include in a skip-level meeting invite:

    • Clearly state the purpose of the meeting.
    • Mention the agenda or key topics for discussion.
    • Include your availability for scheduling.
    • Optionally, you can mention any relevant materials to come prepared with.

    Here's an example:

    Subject: Invitation to Skip-Level Meeting

    Dear [Skip-Level Manager Name],

    I'm hoping to schedule a skip-level meeting with you to discuss my role in [department name] and how it aligns with the company's current strategic goals. I'm particularly interested in learning more about [mention specific area of interest].

    I'm available to meet on [list your availability]. Please let me know what works best for you.

    Thanks, [Your Name]

    Final thoughts

    The success of any skip-level meeting depends on asking the right questions, both for managers and employees.

    When managers ask open-ended and thought-provoking questions during a skip-level meeting, it gets everyone talking and thinking on a deeper level. This kind of discussion can lead to valuable insights and ideas that everyone can implement.

    For employees, these meetings give them a chance to voice their opinions. They can give feedback on the ongoing projects and what kind of resources or skills they need to improve to deliver their best.

    These meetings present a two-way street, with transparent communication at its very core. Give feedback, take feedback, and ask questions. Let it help you create a more open work culture for everyone.

    Try Fireflies for free