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Productivity
Last updated:
May 25, 2025

Skip level meetings explained and 20 smart questions to ask

Skip-level meetings are the secret ingredient for a transparent, connected, and high-performing workplace. They create opportunities for employees to directly engage with senior leaders, bypassing their immediate managers to foster collaboration and understanding. But what exactly goes into a skip-level meeting? How can leaders and employees make the most of them? And what kinds of questions should you ask during these conversations to uncover new insights? This guide is your ultimate resource on skip-level meetings. We’ll cover what they are, how they benefit organizations, and provide 20 impactful questions that leaders can use to connect meaningfully and gather valuable feedback. Additionally, employees will gain actionable tips on how to prepare for these unique meetings.
Written with support from MinutesLink — a free AI notetaker for online meetings.

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Key takeaways

  • Skip-level meetings are a powerful tool for fostering open communication between employees and higher-level leaders, bypassing direct managers to provide fresh perspectives and build stronger organizational connections.
  • These meetings promote transparency, uncover valuable feedback, and help leaders identify challenges or opportunities within their teams that may not surface through regular channels.
  • Both leaders and employees can maximize the value of skip-level meetings by preparing thoughtfully, asking meaningful questions, and using the opportunity to strengthen trust and collaboration.

What is a skip level meeting?

What is a skip level meeting | Effective skip level meetings | Meeting with high level manager

A skip-level meeting is a one-on-one conversation where a senior manager connects with an employee who directly reports to their subordinate manager (often called the "manager’s manager"). This deliberate bypassing of the immediate manager allows senior leaders to gain insights that aren't filtered through layers of hierarchy.

These meetings help organizations uncover hidden opportunities and identify roadblocks, making them instrumental in building rapport and strengthening alignment between teams and leadership.

How are skip level meetings typically conducted?

   Frequency: scheduled quarterly or biannually, depending on organizational needs.
   Participants: a senior leader and one of the team members reporting to a subordinate manager.
   Structure: they remain informal and conversational, avoiding performance reviews. Instead, the focus is on feedback, career growth, team dynamics, and strategic alignment.

Why are skip level meetings important?

Skip-level meetings are a powerful tool for organizations to:

   Encourage open feedback: they bypass the traditional reporting lines and ensure employees feel heard.
   Improve communication across various levels of the organization.
   Spot trends early: leaders gain access to on-the-ground information that they might otherwise miss.
   Boost trust between senior leaders and team members.
   Enable personal connection by fostering rapport and ensuring employees feel valued.

20 smart skip level meeting questions for leaders

If you’re leading a skip-level meeting, the right questions can help you maximize its potential. Use these categories to guide your conversation:

🔍 To understand team dynamics

  1. How’s collaboration on your team?
  2. Is there anything blocking your productivity?
  3. What’s one thing your team is doing really well?
  4. If you could improve one aspect of the team, what would it be?

🧭 To gain insight into leadership and communication

  1. How clear is the company vision to you?
  2. Do you feel your contributions are recognized?
  3. Are there any communication gaps you’ve noticed in the organization?
  4. What feedback would you give leadership to make processes better?

🚀 To explore growth and career development

  1. Are you getting the support you need to grow professionally?
  2. What skills are you interested in developing further?
  3. Do you see a clear path for advancement in the organization?
  4. How well does your current role align with your strengths and aspirations?

📈 To uncover hidden risks or opportunities

  1. What’s something we might be overlooking in our current strategies?
  2. If you were in charge for one day, what changes would you make?
  3. Are there tools or processes slowing you down?
  4. Have you noticed any trends, within the team or market, that we should act on?

💬 To build rapport and connection

  1. What’s been your proudest win at work recently?
  2. What motivates you most in your current role?
  3. How are you doing, both personally and professionally?
  4. Is there anything else you’d like to share that we haven’t covered?

Questions employees should prepare for their skip level meeting

For employees, a skip-level meeting is a rare and valuable opportunity to connect directly with senior leaders. It's a chance to provide insights, build stronger relationships, and gather feedback that can help you grow in your role. Making the most of this interaction requires preparation, intentionality, and a focus on constructive communication. Here’s how you can maximize the value of your skip-level meeting:

   Focus on insights, not complaints
Instead of using the meeting as a space to vent frustrations, approach it as an opportunity to share constructive feedback. Highlight areas where you see opportunities for improvement, but be sure to suggest potential solutions that could address those challenges. This shows initiative and a collaborative mindset.

   Be honest and prepared
Take time before the meeting to reflect on your own work, goals, and contributions to the company. Consider what you’ve accomplished, where you want to grow, and the challenges you may be facing. Coming to the meeting with specific examples and well-thought-out questions will demonstrate your engagement and commitment.

Relevant questions for employees to ask

Skip level meeting questions for direct managers | Skip level meeting questions for employees

Preparation is key to having a productive and meaningful conversation. Here are some thoughtful questions to consider asking during your skip-level meeting:

  • What are your expectations for someone in my role, and how can I ensure I’m meeting or exceeding them?
  • How can I better align my work with the company’s broader goals and priorities?
  • What skills or experiences would you recommend I focus on developing to advance in my career within the company?
  • How does senior leadership envision our team evolving over the next year, and what role could I play in that growth?
  • Are there any upcoming projects or initiatives where I could take on more responsibility or contribute more effectively?
  • What’s the best way for me to share new ideas or suggestions with leadership moving forward?

By asking these kinds of questions, you can gain valuable insights into leadership’s perspective, demonstrate your proactive attitude, and reinforce your commitment to both personal growth and the company’s success. Remember, a skip-level meeting is not just about being heard—it’s about listening, learning, and building a stronger connection to the broader vision of the organization.

Skip level meetings build rapport and organizational value

When conducted effectively, skip-level meetings can provide significant benefits for organizations, fostering better communication and engagement across all levels. Here’s how they make an impact:

   Promote alignment
By giving leadership direct access to employees, skip-level meetings help ensure everyone is aligned on goals, priorities, and expectations. Leaders can gain firsthand insights into day-to-day operations, helping them make more informed decisions that reflect the realities of the team.

   Empower employees
These meetings create a safe space for employees to voice their concerns, share innovative ideas, and offer feedback that may not surface in regular team meetings. It also gives leaders an opportunity to provide tailored guidance and mentorship, fostering professional growth and building trust.

   Reinforce company value
Encouraging open communication through skip-level meetings helps build a culture of transparency, collaboration, and continuous improvement. Employees feel heard and valued, which can lead to improved morale, greater engagement, and stronger commitment to the organization's mission.

How to prepare for a skip level meeting

For leaders

   Review work: get familiar with the employee’s contributions and recent achievements.
   Be curious: approach these meetings with a mindset of openness and genuine interest.
   Set a clear agenda: prepare topics for discussion but leave room for the employee to steer the conversation toward their own priorities.

For employees

   Reflect on achievements: highlight recent successes or significant contributions.
   Discuss goals: use this opportunity to address career aspirations or developmental needs.
   Come with ideas: share suggestions on improving team processes, collaboration, or communication.

Tips for making skip level meetings more effective

Tips for skip level meetings | Tips for upper level managers

Whether you're a senior leader or an employee, these quick tips can help your skip-level meetings achieve their intended outcomes and foster better communication within your organization:

   Keep the atmosphere safe
Building rapport is crucial. Create a judgment-free zone where team members feel comfortable sharing their thoughts, concerns, and ideas without fear of negative consequences. A safe environment encourages transparency and openness.

   Listen more, talk less
Use skip-level meetings as an opportunity to hear directly from employees. Let them do the talking while you focus on listening. Ask open-ended questions to promote authentic communication and uncover insights you might not get otherwise.

   Avoid performance reviews
Skip-level meetings should not feel like evaluations. Instead, treat them as strategic discussions where you can understand broader challenges, identify opportunities for improvement, and empower employees to share feedback about the organization as a whole.

   Follow up with actions
Demonstrating that you value employees’ input is key. Document key takeaways from the meeting and make sure action items are clear, with follow-through that employees can see. Tools like MinutesLink, an AI-powered note-taker, can simplify this process by automatically capturing meeting notes, highlighting important points, and outlining next steps for easy implementation.

By focusing on trust, active listening, and actionable outcomes, skip-level meetings can become powerful tools for driving engagement and organizational growth.

Final thoughts on the benefits of skip level meetings

Skip-level meetings are a simple yet impactful strategy to enhance transparency, improve communication, and drive engagement across layers of an organization. When both leaders and employees participate with preparation and honesty, these interactions uncover valuable insights that contribute to the company’s success.

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Take the next step in enhancing your organizational culture by prioritizing skip-level meetings. And if you want to ensure they’re efficient and effective, consider using tools like MinutesLink to capture meeting notes, action items, and insights with ease. It's the perfect tool for senior leaders looking to save time while staying connected to their teams!

Frequently Asked Questions

What are skip-level meetings?

Skip-level meetings are one-on-one meeting between employees and a manager who is above their direct supervisor, essentially skipping a level of management. These meetings serve as a powerful tool to foster open communication, develop stronger relationships across the organization, and gain valuable insights from employees who may not regularly interact with higher-level leadership. By bypassing the immediate manager, skip-level meetings provide leaders with a more direct understanding of dynamics, workplace challenges, and the overall employee experience, helping to align teams with organizational goals.

What to talk about in skip-level meetings?

The key to a productive skip-level meeting is focusing on relationship-building and gaining meaningful insights. Start by establishing trust with the employee—ask them about their role, their projects, and their experience at the company. Dive deeper into understanding dynamics and ask for honest feedback about challenges they face or obstacles that hinder their work. Encourage them to share their opinions on company processes, workplace culture, or areas for improvement. It's also an excellent opportunity to recognize their efforts, show appreciation for their contributions, and discuss their career growth or long-term aspirations. Keeping the communication open and encouraging candid dialogue will help foster strong connections and provide actionable insights for leadership.

What is the purpose of skip-level meetings?

The main purpose of skip-level meetings is to improve communication within the organization and bridge the gap between employees and higher-level management. These interactions allow leadership to gain unfiltered feedback from employees who are directly involved in day-to-day operations. Skip-level meetings help leaders understand dynamics, challenges, and successes from a fresh perspective. They also create an opportunity to address concerns, boost employee morale, and show that leadership values their input. Additionally, these meetings help build trust and transparency within the organization, fostering a more engaged, motivated workforce aligned with the company’s vision.

Are skip-level meetings bad?

Skip-level meetings aren’t inherently bad, but they require careful handling to avoid potential pitfalls. When conducted thoughtfully, they can be a great way to foster open communication, foster strong connections, and gain insights from employees at all levels. However, if not managed with care, they risk undermining the authority of direct supervisors, creating confusion, or leading to a misinterpretation of feedback. To avoid these issues, leaders should communicate the purpose of the meetings clearly, ensure managers are informed, and use the feedback gathered constructively to support—not bypass—their direct reports. Done right, skip-level meetings are an invaluable tool for building stronger teams and providing leadership with a clearer picture of the organization.

What is a skip-level meeting?

A skip-level meeting is a meeting between a manager and an employee who reports to one of their direct reports, bypassing the employee's immediate supervisor. These meetings are designed to strengthen communication across different levels of the organization, foster strong connections with employees, and gain direct insights into the challenges and successes of day-to-day operations. By skipping a level of management, leaders can understand the team’s perspective directly and identify ways to improve processes, address concerns, or recognize contributions. When done effectively, skip-level meetings help foster a collaborative and open organizational culture.

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