How to prepare for a skip level meeting

JP Baertson

Preparing for a skip level meeting? And before you ask, no—these are not meetings you can skip. A skip level meeting is a one-on-one meeting between two members of an organization who don’t normally have an opportunity to meet. These meetings provide invaluable insight to managers while making employees at all levels of the organization feel seen and heard. 

Let’s talk about what makes a good skip level meeting, how to create a skip level meeting agenda, and key questions for both managers to ask employees and employees to ask managers.

What is a skip level meeting?

A skip level meeting is a one-on-one meeting where a manager’s manager meets directly with an employee—without the employee’s direct manager in attendance. Skip level meetings bypass one level to bring together two people who don’t normally get to meet.

As an employee, you have a chance to meet with someone much higher up in the company, someone you don’t usually have the opportunity to connect with. As the senior manager, you get to meet someone from a different business level who can provide insight into the daily dealings of the business and company morale. Plus, you’ll be making all members of the team feel important and valued.

The benefits of a skip level meeting: 

  • Gain insight into employee morale at all levels
  • Managers get to see what’s really going on across the organization
  • All members of the team feel valued
  • Builds trust across the organization
  • Increases transparency
  • Builds rapport between people who don’t normally work together
  • Goal alignment across all levels of the business
  • Helps managers become transformational leaders

How to prepare for a skip level meeting 

Who are you meeting?

You need to know who you are meeting with—and that goes for both the manager and the employee.

Do some minimal research into the other person's role in the company. If you aren’t familiar with them, make sure you learn their full name and what their position is. Put in the time to learn how to say the other person’s name correctly. Hearing your own name out loud instantly makes people feel more comfortable, and saying a name correctly will show respect to whoever you are meeting with.

If you have met before, refresh your memory so that you can pick up where you left off and continue to build rapport. If possible, follow up on an anecdote you remember about them. For example, if they have spoken to you about a particular hobby, you could ask them how it is going. Or, if you know they like to travel, you could ask where they are headed next.

What’s the purpose of the meeting? 

Every meeting needs a clearly defined purpose and objective. Why are you meeting? What are the goals of the meeting? Clearly defining the purpose of the meeting at the outset will help you establish an effective meeting agenda, and it will ensure the meeting doesn’t end up being a waste of time. 

Both parties should have a clear understanding of why you are meeting and what the goals of the meeting are.

Establish a safe and comfortable space

Keep in mind that this may be an uncomfortable or nerve-racking experience for the employee. It’s up to the higher-ranking person to ensure their teammate feels welcomed and comfortable.

It should be a safe space to speak openly about thoughts, goals, what's working, what isn't, and how the employee feels about their work without fear of the conversation being repeated or gossiped about. One-on-ones are private. They are a chance for open dialogue, free of judgment. It should be clear that the skip level meeting is a time for transparency—it’s not a performance review.

Break the ice and make conversation about topics beyond work. This meeting is a chance to build rapport between two people who generally don’t have much communication in their day-to-day work. Ask questions and follow up when you learn something about the other person. Do all that you can to find common ground. Discuss topics like food, movies, books, music, sports, hobbies, travel, etc.

💡 Learn more about the importance of building rapport in one-on-one meetings and how you can do it successfully.

Prepare skip level meeting questions

Part of preparing for a skip level meeting is determining some questions to ask. Below we’ll outline some common questions employees can ask managers, as well as questions managers can ask employees to build rapport, spark dialogue, and promote transparency.

Skip level meeting questions managers can ask employees:

  • What do you like most about your current position/role?
  • What are your favorite/least favorite work tasks?
  • What do you like to do outside of work?
  • What about our workplace culture would you change?
  • If you were in charge of this company, what’s the first thing you would change?
  • What work are you most proud of from the past year?
  • Would you recommend working here to your friends and family?
  • Do you have any book recommendations for me?
  • Where do you see yourself 5 years from now?
  • Are you content with your current role, or do you hope to move up within the company?
  • What’s something other managers have done to inspire you?
  • Do you feel you are able to do your best work here?
  • Do you feel like you are able to comfortably take your allotted vacation time?
  • Do you feel like you have too much or too little work?
  • Do you ever feel burnt out in your role?
  • What technology, tools, or resources could help you do your job better (if money was no object).
  • Do you have any skills that you don’t think are being fully utilized?
  • Are you interested in taking on more responsibility?

Skip level meeting questions employees should ask leadership:

  • What about our workplace culture would you change?
  • Where do you see the company 5 years from now?
  • Where do you see the company 20 years from now?
  • What training opportunities are available to me?
  • This is where I see myself in 5 years; how do you see me getting there?
  • How can I better support new hires joining our team?
  • Are there any upcoming team building events to look forward to?
  • What do you like to do for fun?
  • What’s the last book you read?
  • Do you have any movie, TV show, or podcast recommendations?
  • What are you most proud of about this organization?
  • Is your job what you expected it to be when you took on your current role?
  • What have past managers done to inspire you?
  • Do you feel like the business is on track to meet this year’s goals?
  • What personal goals do you hope to accomplish in the next 6-12 months?

Creating an agenda for skip level meetings

It’s important to create a skip level meeting agenda with managers, no matter their role. Just because someone has an important position within the company doesn’t mean they can wing a meeting or ignore the predefined meeting agenda. 

The meeting must have an agenda to ensure it stays on track and its objectives are met. While you should aim to make every meeting as effective as possible, this is particularly important for skip level meetings.

Skip level meetings often involve higher up managers who have limited time and busy schedules. The meeting agenda will ensure the meeting stays on track and sticks to the allotted time frame.

What to include in a skip level meeting agenda:

  • Meeting purpose, goals, and objectives
  • Logistics (who, where, when, and time allotted)
  • Previous meeting action items (if you met before)
  • Discussion topics (including time for mutual feedback)

The best meeting agendas are collaborative, which means both people in the meeting get to contribute to it. Collaborative agendas ensure there are no surprises once the meeting begins. Advance planning will reduce the issues or delays that could occur if the attendees are not on the same page.

Planning effective skip level meetings

Charma helps employees and managers at all levels execute skip level meetings with transparent scheduling, simplified agendas, and intentional goal-setting. Stay connected and work with clarity before, during, and after your meetings.

We have a huge library of resources on our website dedicated to improving every type of meeting. Reach out to our team at any time if you have questions about our articles, guides, or products.

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