Remote Academy
8 min read

Uncover Hidden Issues within your Company with Skip-Level Meetings

Published on
April 17, 2024
Phoenix Baker
Product Manager
Lana Steiner
Product Designer
Drew Cano
Frontend Engineer
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Ever feel like your team's got a secret language?

As a leader, you're juggling big decisions, managing managers, and sometimes, it feels like the ground team's whispers never reach your ears. But fear not! There's a simple hack to bridge the gap and uncover hidden gems right under your nose: skip-level meetings.

Think of them as direct lines to unfiltered insights. Forget the corporate ladder, these meetings let you hear straight from the people doing the work, where insightful ideas often hide.

Whether you're a Director, CEO, or anyone managing managers, skip-level meetings are your secret weapon to foster a healthy, vibrant work environment and gain a fresh perspective on what's really going down.

So if you’re ready to leave the whispers behind and tap into the real deal of work conversations, let's dive in!

What is a skip level meeting?

First off, what is a skip level meeting? How do you implement skip level meetings?

Imagine chatting directly with your team, skipping a level in the chain of command. That's a skip-level meeting! It's just a casual, one-on-one talk with an employee your manager oversees.

No need for lengthy formalities, and you can keep them infrequent. But trust me, the insights you gain can be invaluable.

Why would you skip levels?

1. Avoid tunnel vision

As a leader, it's easy to miss ground-level challenges. Skip-level meetings help you dodge tunnel vision and stay in touch with what's really happening.

2. Gain more knowledge & acquire feedback

Get the inside scoop on internal processes, roadblocks, and how to fix them. It's not a performance review, but think of it as gathering intel while boosting team communication, employee engagement and team building.

3. Create a better work environment

Skip-level meetings act like communication superchargers, creating a refreshing way for employees to share ideas and connect with higher-ups. They can skip a level, speak directly, and feel valued, which boosts morale and makes everyone feel more comfortable.

Remember, these meetings are your chance to cheerlead your team and open up their potential!

Preparing for skip level meetings

1. Schedule

Respect your team's schedules by offering flexible meeting times and scheduling through email. Remember, their insights are valuable, so show it!

One-on-ones are ideal. They allow for deeper connections and personalized conversations. If your team is large, consider small group meetings as a temporary solution, but prioritize individual interactions whenever possible.

2. Build an agenda

Build a guiding agenda that you can follow. Include key questions you want to ask, but remain open to honest, spontaneous discussions. This isn't an interview, it's an open dialogue.

Build trust, not walls. Avoid undermining anyone's role or position. Keep the conversation positive and focused on understanding and collaboration.

3. Make it personal

Introduce yourself and encourage your team members to do the same. Share a brief glimpse into your background and ask about theirs. Building rapport helps create a comfortable space for open communication.

Also, “set the scene, but open the floor.” After sharing the meeting's goals, remember it's a two-way street. Encourage questions and be prepared to address their concerns, including those about their career development within the company.

Asking the right skip level meeting questions

It all starts with the questions you ask. But forget fancy jargon and confusing phrasing. We're going for clear, straightforward questions that open the door to honest feedback and give you a peek into the company from your employees' perspective.

What makes an effective skip level meeting question?

  • Keep it open-ended. No leading questions or quizzes here. We want a genuine conversation, not a test.
  • Respect the hierarchy. Don't try to undermine anyone's role or position. Keep it positive and focused on understanding and working together.
  • Be an active listener. Pay attention to their words and emotions. Show them you truly care about what they have to say.

9 Sample questions to get you started 🟢

We went ahead and prepare some sample questions that you may find in a regular skip level meeting to help you get started.

🗣 General questions to enhance communication and leadership

  1. How do you feel about the current state of communication within the team?
  2. Are there any challenges you face in your current role that hinder effective communication?
  3. How can leaders better support you in improving communication?

💬 Specific questions for enhancing communication

  1. How can we improve the flow of information from top to bottom and vice versa?
  2. Are there any barriers that prevent open and transparent communication within the organization?
  3. How can we encourage collaboration and knowledge sharing among different teams?

🤝 Specific questions for enhancing leadership

  1. How can leaders better motivate and inspire employees to excel?
  2. Are there any areas where leaders can provide more guidance and support?
  3. What leadership qualities do you consider most important for the success of the team?

Your next “skip level meeting” template

Here's an introductory agenda you can use for your next meeting:

1. Introduction (5 minutes)

  • Introduce yourself and get to know your employee
  • Share a brief overview of the meeting's purpose

2. Company Updates (5 minutes)

  • Share recent successes or milestones
  • Update on company goals and objectives
  • Overview of any upcoming changes or initiatives
  • Focus the conversation on 1-2 key updates

3. Employee Insights (10-12 minutes)

  • Employees share their experiences and perspectives
  • Discussion on challenges faced in current projects or tasks
  • Suggestions for improvements in processes, communication, or tools
  • Prioritize 1-2 main topics

4. Career Development (5-7 minutes)

  • Discuss career aspirations and growth opportunities
  • Identify potential areas for employee development, provide skill development or training
  • Explore ways to increase engagement and job satisfaction
  • Focus on 1-2 key goals or opportunities

5. Feedback on Management and Leadership (3-5 minutes)

  • Seek feedback on management practices and leadership within the company by asking your questions!
  • Discuss any concerns or suggestions for improvement in leadership styles or decision-making processes

6. Open Forum (5 minutes)

  • Open floor for any additional questions, comments, or discussions
  • Encourage sharing of ideas or feedback that hasn't been covered

30 minutes is a respectful amount of time that respects the employee's schedule and workload. It allows for focused discussions on key topics without feeling rushed or overly long.

Also, keeping the meeting shorter helps maintain the employee's engagement and attention throughout. If needed, additional questions or discussions can be addressed in future meetings or follow-up conversations.

Implementing feedback from skip level meetings

Look at your notes

So you've had your skip-level meetings, gathered gems of feedback, and taken copious notes (good job!). Now comes the crucial part: transforming those insights into real change. Buckle up!

Be strategic when implementing feedback

Don't get overwhelmed by the mountain of feedback. Divide it by theme: what areas did it mostly touch on? Which areas seem most important and doable? Prioritize like a ninja, focusing on tackling the high-impact stuff first.

Have a meeting with your managers

Once you've gathered all the feedback, it’s time to loop in your management team. Schedule a meeting, whip out your notes, and dive into the key points and feedback you gleaned from their teams. Be open and honest, and remember: transparency builds trust.

Keep employee names anonymous when discussing sensitive points. Our goal is a healthier workplace, not witch hunts. Remember, feedback is a gift, even the less sugar-coated kind.


The verdict is in: skip-level meetings are a great addition to your stack. They're not just good for team-building, they're also leadership showcases that open up deeper connections with every team member. By running them regularly and following the tips in this post, you'll see:

  • Increase in engagement: Why? Because your team feels heard, valued, and part of something bigger. Think happy troops, happy work!
  • Leadership cred skyrockets: You become a go-to leader, someone who actively seeks feedback and fosters growth. Way to go, boss!

Just remember:

  • 🔱 It's not about pointing fingers. Skip-level meetings are collaborative feedback hubs, not witch hunts. Let's build each other up!
  • 🌶️ Feedback is a gift, even the spicy kind. Share insights with managers constructively to help them level up their leadership game.
  • 📣 Keep morale soaring. Let your team know their voices matter. Show them their feedback is driving positive change.

So what are you waiting for? Embrace skip-level meetings, and watch your organization thrive.

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