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Meeting Tips

Mastering Skip-Level Meetings: How They Work & Questions to Ask

November 24, 2023
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Last updated
March 21, 2024
Jenna Pitkälä
Mastering Skip-Level Meetings: How They Work & Questions to Ask
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Ever found yourself invited to a skip-level meeting, having no idea how to act during it? Or perhaps you're on the other side, looking to organize one but unsure how?

You're not alone. Skip-level meetings, typically direct conversations between an employee and their manager's manager, are unique in their structure and potential. These intimate sessions, usually spanning 30 minutes to an hour, bypass the immediate chain of command, offering a fresh avenue for communication.

Their true strength? Fostering open communication and understanding. Employees gain a platform to share insights and challenges directly with senior leaders, while managers receive unfiltered employee feedback straight from the frontline.

In this comprehensive skip-level meeting questions guide, we'll navigate the world of skip-level meetings. From their unique benefits to actionable preparation tips, we've got you covered. Plus, we've curated a handy set of questions to ensure your next meeting is a success.

In this blog, you'll learn about...

  • Benefits of Skip-Level Meetings
  • Preparation Tips for Managers
  • Preparation Tips for Employees
  • Common Mistakes to Avoid and What to Do Instead
  • Skip-Level Meeting Agenda Template (For Managers)

Whether you're a seasoned senior manager who has to hold skip-level meetings regularly or an employee stepping into your first skip-level conversation, this guide is your ticket to harnessing the full potential of this unique interaction.

Benefits of Skip-Level Meetings

Skip-level meetings are not your everyday chit-chats between managers and their direct reports, nor are they casual catch-ups with coworkers over coffee. They're rare chances to talk with people outside your normal, daily work bubble.

But what's the point? Well, let's look at some benefits:

  • Gaining a Holistic View of the Organization: Skip-level meetings allow employees to understand the company's broader strategic direction. This helps in aligning individual roles and responsibilities with the larger organizational goals. In return, senior leaders get a ground-level perspective, which might be missed in boardroom discussions. This two-way exchange ensures that the organization moves cohesively towards its objectives.
  • Spotting and Addressing Bottlenecks: Sometimes challenges faced by employees get lost in translation or don't make it up the chain of command. Engaging directly with senior management provides a platform for these issues to be highlighted. It's not about pointing fingers but optimizing processes and ensuring high-performing teams.
  • Enhancing Open Communication: Trust is a pillar of a thriving company culture. Skip-level meetings foster this by creating an environment where employees can communicate candidly with their leaders. This not only boosts employee engagement but also ensures that feedback, both positive and areas of improvement, reaches the decision-makers.

With the potential benefits laid out, the key to harnessing the power of this kind of one-on-one meeting lies in preparation. Whether you're a manager seeking valuable insights or an employee ready to discuss your team's workload, gearing up for the meeting is crucial. And that's what we’ll delve into next.

Preparation Tips for Managers

A successful skip-level meeting hinges on preparation, particularly from the manager's end. Let's break down the steps:

  1. Understand the Purpose: Before sending out that calendar invite, define clear objectives. Are you looking to understand challenges faced by your team members? Or perhaps you want to gain insights into areas of improvement in the work environment? Pinpointing the "why" behind the meeting helps shape the conversation's framework.
  2. Create a Welcoming Atmosphere: Nobody wants to feel like they're on the hot seat. Ensure the environment is non-threatening and welcoming. Reiterate that the goal is good communication and understanding, not a critique fest. Consider starting the meeting with a positive note about the employee's recent achievements. This not only puts the employee at ease but also sets the stage for a constructive dialogue.
  3. Research the Employee's Background: A generic "How's everything going?" won't cut it. Take the time to familiarize yourself with the employee’s role and their contributions to the team. For instance, if you're meeting with someone from the marketing department, be aware and talk their latest campaigns or projects. This demonstrates genuine interest and can lead to more in-depth, meaningful discussions.
  4. Communicate the Skip-Level Meeting Agenda: A well-structured agenda acts as a road map, ensuring the discussion remains focused. Share the agenda in advance so the employee knows what to expect. This could include talking points like team support, work environment, or even broader topics like company culture. An informed employee is more likely to come prepared, making the discussion richer.

Potential Questions to Ask Employees

In addition to the steps above, it's a good idea to prepare some questions in advance. Remember, aim for open-ended skip-level meeting questions that foster a genuine conversation.

  • How do you see your role evolving within the company?
  • If you could redesign your job description, what would you change?
  • How do you feel your work aligns with the company's mission and values?
  • What's one thing you wish senior management knew about your role or department?
  • What resources or tools do you feel are lacking in your current work environment?
  • How do you perceive the company's current state in terms of employee engagement and satisfaction?
  • Are there any challenges you believe are hindering our team's goals?
  • How can senior management better support you and your team's workload?
  • In terms of company culture, what changes would you suggest to create a more inclusive environment?
  • Are there any areas of professional growth you're keen to explore?

Preparation Tips for Employees

Navigating a skip-level meeting can seem daunting for employees. After all, it's not every day you sit across from your boss' boss. But with the right preparation, it can be an opportunity to shine and make your voice heard. Let’s delve into the steps:

  1. Reflect on Your Role and Contributions: Before the meeting, take a moment to review your achievements and the impact you've made. This could be in terms of projects you've led, initiatives you've been a part of, or even innovative ideas you've brought to the table. Knowing your milestones will help you articulate them effectively and showcase your dedication.
  2. Frame Feedback Constructively: If you have concerns or suggestions, it's essential to present them in a positive and constructive manner. Instead of focusing on what's not working, highlight opportunities for improvement. It’s more effective to say, “I believe our team could benefit from more frequent communication,” rather than, “We never know what’s going on.” when giving your feedback.
  3. Align with the Bigger Picture: Understand how your role fits into the company's larger objectives. This perspective allows you to engage in discussions that are not just about your immediate role but also about how you contribute to the company's overall success.

Questions You Can Ask Your Leaders

Have the most important questions you want to ask ready at your fingertips, so you make sure not to forget them. Remember, the goal is to foster better understanding and collaboration. Here are some open-ended skip -level meeting questions to get you started:

  • How do senior leaders view the direction our team is headed in?
  • What are the company's goals for the next quarter or year, and how can I align my role to support them?
  • Are there specific skills or training that the management feels would benefit our team or department?
  • How can I contribute more effectively to the company's current objectives?
  • What changes or improvements are anticipated in the larger organization that might impact our team?
  • Are there opportunities for professional growth or mentorship within the organization?
  • How does senior management perceive our team's current performance and areas of improvement?

Common Mistakes to Avoid and What to Do Instead

Skip-level meetings can be a game-changer, but like any game, there are pitfalls to avoid. Whether you're the manager or the employee, being aware of these common mistakes can help steer the meeting toward a productive and positive outcome.

1. Not Setting Clear Expectations

The Mistake: Not letting employees know what to expect from the meeting.

Instead: Clearly communicate the purpose, agenda, and objectives beforehand. It helps in setting the right tone and ensures all attendees are on the same page.

2. Lack of Adequate Preparation

The Mistake: Treating it like any other meeting and not preparing in advance.

Instead: Both managers and employees should come prepared with talking points, questions, and a clear understanding of the meeting's objectives. Remember, the more prepared you are, the more fruitful the discussion. Check out the agenda template in this blog to help you with preparation.

3. Failing to Properly Document Insights

The Mistake: Not capturing insights during the skip-level meeting or jotting down notes hastily that are hard to decipher later.

Instead: Utilize tools like Wudpecker's note-taking tool that streamline this process. By automatically capturing and summarizing discussions, Wudpecker ensures that no crucial details are missed. This not only provides a reliable record of the meeting but also allows participants to remain fully engaged in the conversation without the distraction of manual note-taking.

Having clear, concise summaries to refer back to later ensures that insights are acted upon, driving meaningful change.

For this reason, you might want to consider Wudpecker, whose AI-note-taking tool...

  • Automatically joins and records your meetings, so there's no repeated setup
  • Summarizes the whole online meeting's discussions and action items for you (Note: if you're not meeting online, you can still set up a recording system in your physical room)
  • Takes max 10 (usually 1-2) minutes after the meeting to give you the summary
  • Is compatible with Google Meet, Zoom, and Microsoft Teams
  • Keeps record of notes from any previous meeting where Wudpecker was a participant.
  • Allows multiple people to have their own Wudpecker recorder in the meeting at the same time and receive their own notes in their account afterward
  • Lets you share the notes to other people
An example of Wudpecker's automatically generated meeting notes, including TL;DR, Summary and Action Items.
A simplified example of what Wudpecker's meeting notes can look like.

4. Mistaking it for a Feedback Session for Direct Managers

The Mistake: Using the meeting solely to provide feedback about direct managers.

Instead: Focus on broader organizational issues, team dynamics, and personal growth. While it's okay to discuss challenges faced with direct managers, the conversation shouldn't revolve solely around this.

5. Not Acting on Insights Gathered

The Mistake: Collecting feedback and insights but not acting on them.

Instead: Demonstrating that you value the discussion by implementing changes or addressing concerns is crucial. It reinforces trust and shows commitment to improvement.

6. Viewing it as a One-Time Event

The Mistake: Holding one skip-level meeting and then forgetting about it.

Instead: Consider it as a recurring dialogue. Building relationships and working communication channels takes time and consistent effort.

By sidestepping these pitfalls and adopting the suggested practices, skip-level meetings can become an invaluable tool for fostering understanding, enhancing team dynamics, and driving organizational success.

Free Agenda Template

As you use the suggested skip-level meeting agenda below, you'll notice some practical example sentences included. These are intended to guide you and offer context on how you might approach each segment of the meeting. However, before you share this agenda with your employee, remember to remove these example sentences as you're editing the agenda for your needs.


Effective skip-level meetings stand as a unique opportunity in the corporate landscape, bridging communication gaps and fostering understanding between different levels of an organization. With the right preparation, like the skip-level meeting questions and agenda template we provided in this blog, these meetings can be instrumental in aligning lower level employees' individual aspirations with overarching company goals.

Whether you're an employee diving deep into team feedback or a manager eager to enhance company culture, approach these meetings as more than just a dialogue. Embrace them as a pivotal tool for growth, collaboration, and positive organizational change.


What should be discussed in a skip-level meeting?

Skip-level meetings aim to bridge communication gaps, align team goals with company strategy, and foster mutual understanding. While discussions can range from clarifying roles to understanding future directions, specific questions help steer the dialogue. Here are some examples of skip-level meeting questions for both managers and employees:

For the manager:

  • How do you feel your work aligns with the company's mission and values?
  • What's one thing you wish senior management knew about your role or department?
  • How can senior management better support you and your team's workload?

For the employee:

  • How do senior leaders view the direction our team is headed in?
  • What are the company's goals for the next quarter or year, and how can I align my role to support them?
  • How does senior management perceive our team's current performance and areas of improvement?

How do you ace a skip-level meeting?

Employee Perspective: Align your points with company goals and approach it as a constructive dialogue. Have skip-level meeting questions ready and remember, it's a chance to communicate with your boss's boss.

Manager Perspective: Success in a skip-level meeting requires listening and guiding. Prepare open-ended questions and be familiar with the employee's role. Stay open to manager feedback and ensure a collaborative tone.

What do you get out of a skip-level meeting?

Beyond open communication, these meetings provide a platform to understand the company's strategic direction, build relationships with senior leaders, and voice concerns or ideas that might not surface in regular team meetings.

What are the disadvantages of a skip-level meeting?

If not handled correctly, they can lead to misunderstandings, create a feeling of going behind a direct manager's back, or even foster a sense of favoritism for one team member.

How many people are in a skip-level meeting?

Typically, it's a one-on-one meeting between an employee and their manager's manager. However, in some organizations or specific scenarios, it might involve a small group of employees for a more collaborative discussion.

How long is a skip-level meeting?

Skip-level meetings typically last between 30 minutes to an hour. The exact duration can vary based on the topics to be discussed and the preferences of the participants. It's essential to allocate enough time to ensure a productive conversation without making the meeting overly lengthy.

How often should skip-level meetings be held?

The frequency of skip-level meetings can vary based on the organization's needs and goals. However, many companies find value in conducting them quarterly. This regularity ensures that communication lines remain open, but not so frequent that it becomes burdensome or redundant.

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Skip-Level Meeting Agenda For Managers (Copyable Template)

Date: [Insert Date]
Time: [Insert Start Time] - [Insert End Time]
Location: [Specify if it's an in-person or virtual meeting and provide necessary details or links]

1. Opening (5 minutes)

  • Setting the tone and reiterating the purpose.
  • Example: "Thank you for joining today. The goal of this skip-level meeting is to foster open communication, understand challenges, and discuss ways we can support each other better."

2. Employee Sharing (15 minutes)

  • Allowing the employee to share their experiences, challenges, and suggestions.
  • Example: "Can you share any recent experiences or challenges, perhaps something like the Alpha Project, where you identified areas for improvement or had suggestions?"

3. Manager's Queries (15 minutes)

  • Open-ended questions to understand the employee's perspective better.
  • Example: "From your viewpoint, how do you think the recent changes in the marketing department have impacted our overall team dynamics?"

4. Discussion on Feedback (10 minutes)

  • Discuss feedback points constructively.
  • Example: "I appreciate your insights on the collaboration tools. I've heard similar feedback from other teams. Let's explore potential solutions."

5. Conclusion (5 minutes)

  • Summarizing the discussions and outlining the next steps.
  • Example: "Today, we've identified some key areas for improvement, especially around our collaboration tools. Let's work on a plan to address this."

Notes and Pre-Meeting Reads

  • Possible reminders, questions, any other pre-meeting items
Mastering Skip-Level Meetings: How They Work & Questions to Ask
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Mastering Skip-Level Meetings: How They Work & Questions to Ask
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Mastering Skip-Level Meetings: How They Work & Questions to Ask
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