Skip Level Meeting Questions and Agenda Updated for 2024

By Ted Skinner

4 Steps to A Great Skip-Level Meeting Process.png

dateFri, Apr 19, 2024 @ 08:18 AM

What is a skip-level meeting?

As defined in an article by Jared Lewis, "In a skip-level meeting, skip level meeting questions to askupper-level management bypasses mid-level management to talk directly to non-managerial employees."  The manager meets with employees to understand their team members better, build trust in the organization, and get a better sense of the work environment and the challenges facing your front-line employees. Skip-level meetings for employees are just as crucial as for managers, and both should be well prepared before the "skip-level meeting." to get employee feedback. Effective skip level meetings are an effective tool to improve organizational communications, employee engagement, and great one-on-one meetings.

Skip Level Meeting Questions

There is considerable evidence that great skip-level meetings (or "skip meetings") have multiple potential benefits. These include everything from helping them make better long-term strategic decisions by better understanding their customers from those who interact with them to improving employee engagement by establishing more personal relationships and quicker resolution times by getting closer to the source. Teams that are more engaged with their managers tend to be higher-performing teams and have a better sense of alignment, focus, and purpose. 

You can follow these four concepts to decide what to discuss in a skip-level meeting with an employee.

Skip Level Meeting Agenda Template:

1. Understand the Purpose of a Skip Level Meeting

According to Lewis, "The primary purpose of the skip-level meeting within an organization is to determine the organization's effectiveness -- by getting an honest assessment from employees at all levels."  These meetings are crucial for day-to-day operations and allow the upper manager to remove the most significant challenge impacting performance.

Skip-level meetings allow senior managers to talk to employees freely without fear of retribution. Senior leaders can speak directly to their employees instead of through messengers, enabling them to see whether their direct reports are truthful or hiding issues. The one-on-one format allows for collaboration between the senior manager and the individual contributor. It should enable the manager and the employee to feel comfortable and have an open and honest conversation.

2. Ensure Anonymity for Free Discussions

The bedrock of skip-level meetings is that employees can speak freely without fear of retribution. If employees fear retaliation, they will not be as open, undermining the whole point of skip-level meetings and the insight they provide. This is especially important if the senior leader hopes to learn about mid-level managers' performance and effectiveness from their direct reports.

Before you start the process, assure your employees that they will be anonymous. Put them at ease so they won't face a backlash if they speak their minds. You can only get the full benefits of skip-level meetings when this occurs.

Skip Level Meeting Questions Video

3. Plan Ahead for Your Skip Level Meeting

According to Lewis, "Conducting skip-level meetings requires considerable advanced planning. Since skip-level meetings are effective because they provide upper-level managers with information normally unavailable, planning is essential—and those executives planning a meeting need to establish a specific purpose."

As with any meeting you run, think and plan how your skip-level sessions will go. Remember that you need to ensure total anonymity for each employee involved. You need to provide the skip-level meeting agenda ahead of time to the employees as they may be nervous about meeting with "their direct manager's boss" or "manager's manager," and allowing them the time to prepare would be helpful. Please get in the mindset to be open to all kinds of feedback and take them as positive ways to make your organization more effective; many employees will feel nervous - like they are preparing for an executive team meeting.

Think about the purpose of the skip-level meetings. Is it to determine managerial effectiveness, organizational alignment, organizational issues, etc.? It can't be all the above, so please make sure that you keep some specific questions on the area you are focusing on, but be able to adjust if the team member has something specific that they think is necessary.

Once you know the purpose of the meetings, you can plan and map out your process for effective skip-level meetings. If used properly, these meetings are a significant part of working on a highly productive team, and you never know where innovative ideas will come from.

4. Consider and Manage Risk in Skip Level Meetings

Keep the whole purpose of skip-level meetings in mind. Lewis says, "Skip-level meetings should not be used as an opportunity to conduct a witch hunt against mid-level managers."  With the talent war raging through the economy, having as many touchpoints with your team as possible is more important than ever to attract and retain top talent to win the talent war.

These meetings are for senior leaders to gain a fuller understanding of their organization from a high level. Try to keep risk low for both employees and managers so that they can fully contribute to the process. This is another opportunity for managers to spend time with the organization and hear the issues "from the ground up." Employees should also be ready with skip level meeting questions to ask their boss or manager. The better prepared both sides are for the conversion, the more effective it will be. Skip meetings can be missing from your employee engagement and team accountability culture.   We've compiled a list of the best skip-level meeting questions to share with you so you know what to discuss in skip-level meetings.

Skip-Level Meeting Questions:

  • What is some good news that you'd like to share?
  • What do you believe are the most significant challenges our team should be addressing?
  • Given the company's long-term strategy, how do you envision our team’s role evolving?
  • Based on your observations, how can I grow better to support our immediate team and the larger organization?
  • What trends or changes in the market should we be paying attention to or learning from?
  • When you envision our company five or ten years later, what key milestones do you hope we’ve achieved?
  • Given the challenges our industry faces, what keeps you hopeful?
  • What projects at work have you most enjoyed working on?
  • What is your favorite thing to do outside of work?
  • What is the biggest issue facing your role in the organization?
  • If there was one thing that you could "fix" in the company, what would it be?
  • How would you change things if you were in my shoes?
  • How could we better leverage your unique skill set?
  • Would you recommend working here to your friends?
    • Why?
    • Why not?
  • What is keeping you from being more successful than you already are?
  • What are your goals in the next 3 to 5 years?
  • What is your favorite book, podcast, or movie?
  • How can we help you achieve those goals?
  • What would you do differently if you were the manager of your team?
  • Would you happen to know the company's goals?
  • What can we do to make you happy with your role?
  • What do you need from the leadership team?
  • Would you happen to know how your team's goals support the company?
  • What are your goals for the next few years?
  • Is there anything else that we should have discussed?
  • Is there anything else that I can do to help you and your team?
  • Do you know how we can help you work with your manager?
  • What is your favorite part of the company?
  • What is your least favorite part of the company?
  • When have you felt most proud of being part of this organization?
  • Are you happy with your role?
  • If you are meeting with a manager, ask if they have regular meetings with their direct reports.
  • What are our team's most significant challenges right now?
  • What progress have you seen in the department over the last quarter and why?
  • What initiatives or projects should we launch next to create more value for the business?
  • How can we increase collaboration between different departments and teams within the organization?
  • What do employees need from management to succeed, and what changes must be introduced to achieve this goal?
  • How can we improve customer service across all our products and services?
  • Are there any new technologies that could help us create more efficient, cost-effective processes within our company?
  • How are we tracking against Senior Executives' goals in terms of performance and innovation?
  • What strategies have worked best for our team so far to increase customer loyalty and satisfaction with our brand?
  • Are there any areas where greater focus is needed for us to stay ahead of competitors regarding customer experience, product quality, or technological advancement?
  • Are there any project risks your team currently faces that need additional support from higher-level management or other departments outside ours?
  • How can we ensure open communication channels between staff members at different levels to promote a collaborative culture within the organization?
  • Does everyone on your team have the necessary skills to perform their role, or do certain positions effectively require additional training or further development opportunities, such as employee workshops or conferences?

At Rhythm Systems, we understand your challenges as leaders of fast-growing companies. Our integrated Business Operating System helps your executive team unlock seamless strategy execution and sustainable growth. With AI-powered software, our Think Plan Do™ methodology, and expert coaching, we ensure your team is focused, aligned, and accountable to strategic goals. Our clients, from dynamic organizations to larger enterprises, have seen 10X faster growth and sustained success. Join them and discover how the Rhythm System can elevate your business and lead to winning execution quarter after quarter.


Ted Skinner

Additional Rhythm Systems Resources for Team Meetings:

How To Have Effective Weekly Staff Meetings (With Sample Agenda Template)

Download our weekly meeting agenda template

Do You Have Weekly Meetings with Yourself?

Management Meeting Agenda: Make Your Management Meetings More Effective

8 Ways to Make Weekly Meetings Strategic vs. Tactical (Video)

Weekly Adjustment Meetings vs. Weekly Status Meetings (Infographic)

Consider using Rhythm Software to run your weekly meeting, where the status and agenda are automatically created weekly to keep you on track!

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Ted Skinner


Photo Credit: iStock by Getty Images