How to Make the Most out of a Skip-level Meeting (Guide + Templates)

Skip-level meetings can be a powerful tool to accelerate your career and grow the company. Practice it with our AI bot + example questions to ask.
Evelyn Le
Evelyn Le
Strategic Product Lead, Stay Ahead, FlexOS
With a rich background in communication research and analysis, Evelyn guides readers with expertise, offering innovative advice in the digital work.
October 25, 2023
min read

“Everyone in the company is working toward a shared goal.”

This statement is every company leader’s dream. 

But the reality is far off, as recent research shows. 

According to Gallup, only 41% of US employees strongly agree that they know what their company stands for, and only 20% feel connected to the company’s culture. 

Meanwhile, organizational leaders are twice as likely than employees to feel the company’s values.

Therefore, building direct connections between company leaders and people across the organization can raise engagement and improve performance.

And not just for juniors. 

Ron Ashkenas, a leadership consultant and the co-author of Harvard Business Review Leader’s Handbook, states that it is common for senior leadership to feel isolated. 

This executive isolation can compromise decision-making and work effectiveness. 

Skip-level meetings, he suggests, are the perfect antidote.

Practice Chatbot: Want to practice in a mock skip-level meeting? Or extract helpful information about the topic quickly? Do it here!

Lexi was trained to let you prepare for your skip-level meeting in the most practical way. You can maximize her by:

  • Start by stating your purpose: Practice for a skip-level meeting, or asking general questions.
  • You can ask Lexi to: Ask you a question and give you feedback on your answer, or let you ask a question and give feedback on how to make the question better.
  • Ask Lexi about anything about skip-level meetings.

What is a skip-level meeting?

I have deeply appreciated skip–level meetings with my bosses’ boss, which excited me to do more research on the topic and share it with you.

The first thing I wanted to understand is what skip-level meetings really are.

Skip-level meetings are “meetings where senior leaders get to hear directly from operational, front-line employees, or a recommended interventional exercise to get feedback from staff members,” says leadership expert Paul Falcone in SHRM Online.

"Skip-level meetings are meetings where senior leaders get to hear directly from operational, front-line employees, or a recommended interventional exercise to get feedback from staff members." – Paul Falcone, best-selling Leadership Expert

In short, a skip-level meeting is when you “skip” a hierarchy level, either up or down, to meet directly with the manager of your manager (or vice versa.)

This means you speak with someone you do not have frequent professional interactions with. 

As Paul points out, this is helpful, as “the immediate leader's presence may bias results or hinder honest and open feedback.”

For example, if you’re a Business Senior Associate, a skip-level meeting would be a direct meeting:

  • between you and the Director, instead of your direct supervisor being the Senior Manager, or
  • between you and the Business Analyst, whose direct supervisor is under your management, being the Business Associate.
a hierarchy structure to show how skip-level meeting is between a Senior  Business Associate with Director or with Business Analyst.
Visualization of skip-level meeting

Also, it's worth keeping in mind that a Skip-Level Meeting is NOT:

1) A job promotion interview.

The goal is to contribute insightful comments and not to put yourself in a favorable light for future promotions.

2) A therapy session.

You can provide helpful feedback on your direct manager or the company, but don’t endlessly complain or gossip. Every problem you pose should have a suggested solution.

3) A performance review.

Performance reviews are best conducted directly with the manager. 

Benefits of skip-level meetings

Skip-level meetings benefit team members and managers by providing opportunities to align with company goals, recognize accomplishments, build career roadmaps, and identify potential issues.

A skip-level meeting with a higher-up helps you as a team player to:

1) Build a sense of purpose

You can be a good team player by nailing your immediate priorities. But you can be great when you have a sense of purpose in your work.

Listening to your supervisor’s manager about the company's vision and critical business priorities can help you connect to them more. 

2) Gain recognition

Recognition matters.

Having a chance to profile your work, communicate your ideas, and get recognized by higher-ups can help you get recognized and fuel your motivation.

3) Build a career roadmap

Listening to your higher-ups can help you envision what is waiting for you ahead, what the expectations are, and how you can meet them. 

4) Practice managing up

Learning senior leaders’ expectations, understanding what can be improved, and proposing your initiatives help you contribute to company priorities.

A skip-level meeting with a junior can help you as the manager to:

1) Strengthen team alignment

Skip-level interactions ensure everyone is on the same page. It lets you deliver the company’s mission, vision, and values.

The meeting can also help you understand where there’s room for improvement in connecting people’s day-to-day work and your objectives.

2) Understand team dynamics

Getting to know the members you indirectly manage gives you a sense of each team’s working style. This can inform a strategy for maximizing their full potential. 

3) Get closer to the ground

As Ron Ashkenas points out, skip-level meetings help you “get out your bubble.”

You hear perspectives from people working directly with the market and consumers. This will help you make more informed and inclusive decisions.

4) Retain talent

Listening to unfiltered comments and insights from juniors helps you to work on identified problems and inconveniences promptly.

Listening to feedback in a skip-level meeting is better than hearing it in an exit interview. 

6 Dos and Don’ts in Conducting Skip-Level Meetings

Before getting into specific questions and meeting flow, this checklist helps you understand the must-haves before, during, and after your skip-level meetings.

Dos and Don'ts in skip-level meetings.
Dos and Don'ts in skip-level meetings.

Your skip-level meetings will be a fantastic experience if you DO…


1) Make sure your direct manager is aware of the skip-level meeting to avoid confusion. 

Give them a heads-up and keep them in the loop. This shows respect, avoids misunderstandings, and enhances a strong relationship. Your manager can even help you prepare.

2) Whether you initiated the meeting or not, include an outlined agenda with your goals

3) Have a list of questions ready. But don’t feel pressured to check them all off during the meeting, it’s more important to let the conversation flow.

During the meeting:

4) Listen attentively. Treat this like a conversation where two people engage in the topic and with each other. 

5) Provide your personal experience and insights. It’s not about what you think the manager expects you to say or feel, it is your experience that matters as a valuable insight.

After the meeting:

6) A follow-up email to thank them for their time and propose the next skip-level meeting (if applicable.)

And DON’T…


1) Send out an invitation without any context. Be clear about your intent and include the agenda. 

During the meeting:

2) Record without asking for consent. While having detailed meeting notes can be helpful, this might harm the sense of trust.

3) Make an immediate promise. Instead, note the discussion topic or request and say that you’ll revert.

4) Gossiping. As discussed above, there’s no place for gossiping at work, especially not in a skip-level meeting. Instead, provide concrete feedback.

After the meeting:

5) Be a stranger when running into the person. The meeting shouldn’t be the only time you speak to the person. Instead, maintain the relationship. 

6) Spread what you discussed without asking for consent. Because the information you heard was likely shared in confidence and not for broad distribution. 

Email templates and questions for skip-level meetings

 To conduct a skip-level meeting, follow these steps:

  1. Send an invite to your higher-up or your junior.
  2. Send an email or message to inform the direct manager about the meeting.
  3. Prepare a list of questions to ask in the meeting and share them ahead of time if possible and appropriate.
  4. Listen and take notes (where appropriate.)
  5. Follow up. 

Meet-Up: A meeting between you and your supervisor’s manager

The email you send is the first impression for the person you want to meet with. 

It should be concise and clear about your objectives.

Email template for a skip-level meeting with your manager’s boss:

Dear [higher-up’s name],
My name is [your name], and I am a [your job title] at [the department]. I’m reaching out to ask for a skip-level meeting.
I believe a skip-level meeting with you can help me:
- Have a clearer understanding of the company’s vision and priorities
- Understand how my work can contribute towards the common goal
- Learn about specific expectations and requirements to level up my career
- Learn about your career roadmap and professional advice
- Offer ideas on how to improve our company culture
This meeting should not take more than an hour. It can also be a coffee or lunch, whatever is convenient for you. 
My manager, [name], is aware of this meeting request and I will keep them posted on our discussion.
Please let me know if this meeting sounds good and share a timeslot that works for you.
I’m looking forward to your response.
Warmest Regards,
[Your name]

Questions to ask in your skip-level meeting with higher-ups

Asking good questions in your skip-level meeting with higher-ups positions you as a thoughtful and valuable team member, benefiting you personally and professionally. Questions to ask include:

About the company:

  1. How would you describe the mission and vision of the company?
  2. What could our team improve to match the company’s vision? How about myself?
  3. What key milestones do you want this company to achieve in the next 1, 5, and 5-10 years?
  4. What do you see as a challenge our team should be addressing?
  5. What are the available resources for our team for [topic or challenge]?
  6. What are the current market trends we should pay attention to?
  7. How would you describe our (ideal) company culture? Where can we improve it?

About their leadership and decision-making:

  1. Can you tell me more about your thinking process behind the decision of [recent policies/announcements/changes]?
  2. How can I learn to make decisions more strategically?
  3. How would you define “good leadership,” and how would you define your style?
  4. What podcasts or newsletters  you would recommend? Who inspires you?
  5. Who are some influencers in our field you would recommend?

About their career:

  1. What was your early career like? 
  2. Did you seek mentorship in your career? If yes, where did you seek it?
  3. What is your “checklist” to commit to a company?
  4. What about your career keeps you going?
Notion template for skip-level meeting.

Meet-Down: A meeting between you and your junior

To initiate a meeting with a junior, be careful with your invite. You don’t want to scare them off with an intimidating email from their manager’s boss. 

Try to make it friendly, straightforward, and conversational. 

Email template to initiate a skip-level meeting with a junior

Hi [name],
I hope everything is going well and you are enjoying your role with [company name]. 
I am planning to conduct skip-level meetings with team members of my direct reports to learn more about what’s happening in our company and how I can improve your experience with us.
This is a one-on-one meeting where I can learn more about you: Your work, what keeps you motivated, what hinders you, your feedback, and insights on how the company is doing. 
The meeting is rather casual and low-stakes. We will ask each other questions, and I will listen to you most of the time. No critical decision will be made.
Your insights can help me tremendously in how I can do better for you and the company.
I informed your manager about the meeting so there should be no surprises. Please choose a timeslot in my calendar here that works for you. 
Looking forward to talking!
[Your name]

Don’t forget to inform the direct manager about your plan of conducting skip-level meetings. This is crucial in trust-building between different stakeholders.

Email template to inform the direct manager

Hi [their name],
To reflect on the company's performance and explore ways to improve, I am planning to conduct skip-level meetings with team members of my direct reports.
The aim of these meetings is for me to gather data, insights, and new ideas to be a better leader to you and your team and create better ways of working for the company as a whole. I will keep you posted about insights from your team.
These are one-on-one meetings where I can learn more about the team members personally: Their work, what keeps them motivated, what hinders them, their feedback, and insights on how the company is doing. 
The meeting is rather casual and low-stakes. No critical decisions will be made, at least during the meeting. We will not directly discuss you or your performance as a manager, but if something comes up along those lines, I will be sure to discuss it with you.
Please let me know if you have any questions or concerns about skip-level meetings. I am happy to have a quick call to explain further.
Thank you for your support!
[Your name]

Questions to ask in your skip-level meeting with juniors

In skip-level meetings, your goal is to ask questions to understand the team members, how they can help the company grow, and how you can help them grow: 

Questions about their roles, goals, and blockers:

  1. How do you understand our company’s vision and mission?
  2. What do you know about our company’s strategy and goals?   Which goals are you contributing to directly?
  3. How can your team, manager, or myself help you do your job better?
  4. What are the current hindrances at your work?
  5. Do you feel like you have enough resources and support to do your work?
  6. Have you ever felt conflicted between what I said and what your direct manager assigned you to do?
  7. Are you in a any communities that can support you with your job?
  8. Do you feel like you have enough balance in your work-personal life?
  9. Do you have any personal projects you are working on? 

About their career:

  1. What do you want to learn in this job?
  2. Do you have 3-6-9 months objectives of what you want to achieve here?
  3. What are your career aspirations (beyond your current job)?
  4. Is there any company role that is outside your scope but you want to learn more from?
  5. What about this career that makes you excited?
  6. Is there any niche in this field you want to dig deeper into?

About ideas they may have [as they’re younger, they may have insights into younger consumers/customer segments, for example]:

  1. If money and job title would not be an issue, how would you change what we do?
  2. If you were the CEO of this company, what would you change?
  3. What new products or services do you think we should offer? 

More questions to ask in your skip-level meetings? Check out our list of one-on-one questions. We have more than 200 questions, grouped in different categories, for you to select from.

Skip-level Meeting: Frequently Asked Questions

Should I share the content of my skip-level meeting with anyone?

Usually not, but depends on the confidentiality of the content you share in the meeting. 

Always check with the person you were in the meeting with if you want to share any of the information with anyone else. 

How often should I have a skip-level meeting?

It depends on the objective of the skip-level meeting, whether you want to gather insights for a project or want to build relationships. It can range from once per month to once per year.

And as discussed, whether you have it next week or just decide to propose for one, take the opportunity and turn your skip-level meetings into a great conversation ever. Head to Lexi to practice in a mock conversation and make the most out of yours!

Make any skip-level meeting even better with these free Office Backgrounds for Zoom (and Teams + Google Meet.)

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