Skip-Level Meetings: Questions and Guidance For Employees and Managers

Skip-level meetings have been a tool in the arsenal of managers for decades, yet even these days they remain a challenge.

Part of the reason is that managers think that skip-level meetings are a virtue on their own, and somehow things will turn out better if employees simply meet with their boss’s boss.

Truth is, there are as many wrong as there are right ways a skip-level meeting can go.

In this article, we’ll navigate the pitfalls of skip-level meetings, the most efficient way of running them, and how to best prepare for meetings as both employees and skip-level managers. 

What Is a Skip Level Meeting?

Skip-level is a meeting between employees and managers they don’t directly report to. The most common form of a skip-level meeting takes place between an employee and their manager’s manager.

Skip-level meetings can also (rarely) refer to meetings between employees and managers from other departments or parts of an organization.

It’s possible to skip several levels of management and hold meetings between a skip manager and several people rather than a single employee. It’s crucial, however, that the direct manager of an employee doesn’t participate in any type of skip-level meeting. 

There are two types of skip-level meetings: 1-on-1 skip-level meetings and team skip-level meetings. In 1-on-1 sessions, only two people are present: an employee and a skip-level manager. In team skip-level meetings, a senior manager can speak with an entire team that he or she does not directly manage.

What’s The Purpose of Skip-Level Meeting?

The main purpose of skip-level meetings is to provide high-level managers and regular employees with unique benefits and perspectives on the company’s performance that would otherwise be difficult to attain through standard team meetings and one-on-one sessions with direct management.

As skip-level meetings prove advantageous to both employees and leaders, let’s cover the benefits these meetings provide to each party. 

Benefits of Skip-Level Meetings For Managers

• Better understand what’s going on at a project level. Reports provided by middle managers to senior managers often simplify or abstract certain aspects of how the company operates, mainly to save time and support strategic decisions. Ground-level data from employees helps managers gain a fresh perspective, understand nuances of company processes, and come up with fresh ideas.
  
• Improve company transparency. Transparency is crucial when you want your employees to face challenges up front rather than avoiding them for months. Skip-level meetings help managers to promote transparency across several levels of the organization’s hierarchy. Higher transparency leads to a more open creative environment and helps to early detect issues that hinder productivity.
  
• Evaluate the impact of specific initiatives. Senior managers often make decisions and facilitate policies to improve major aspects of their company. Yet sometimes only through talking to regular employees can they understand if these changes actually made an impact.
  
• Learn about company-wide issues. Sometimes the only way to reveal a certain issue that affects the entire company is by talking to people who might be affected by it the most. Often these people are regular employees rather than middle-level managers.
  
• Boost employee loyalty and reduce turnover. By forming and sustaining relationships with employees you will help them integrate into your company even more and better understand their role, reducing turnover.

Benefits of Skip-Level Meetings For Employees

• Share and resolve issues that are impossible to deal with at your manager’s level. Some issues, such as company-wide policy, or certain tradition that stands in a way of progress, can only be fixed at the level where they originated.
  
• Feel valued and heard. Employees that are in direct contact with high-end management feel more recognized and valued. Both of these factors lead to increased motivation and transparency.
  
• Understand the company’s priorities. By talking to senior managers, employees can better understand where the company is directed at the moment and how to maximize the impact of their work.
  
• Learn from executives. Often executives have the unique experience of running a company, and this experience will prove useful no matter if you go higher up in the ranks or not. 

Skip-Meeting Agenda: How to Run Effective Skip-Level Meetings

Without a balanced agenda and some preparation, skip-level meetings can lose most of their benefits. 

Below are the main stages of every skip-level meeting worth attending.

1. Prepare

Preparation is the most critical step of skip level meetings as it allows you to set proper expectations for participants, focus on what’s important, and better control the outcome of your meetings. 

Employees can write down a list of questions or topics they would like to discuss with their manager’s manager. Next to every question write a short explanation of why you want to discuss this topic and why you think it’s a good idea to discuss it with your boss’s boss rather than your immediate manager. Even the mere fact of writing the topics down will help you prioritize certain questions or drop the unnecessary ones. 

Managers will benefit from more extensive preparation for skip-level meetings akin to preparing for 1-on-1 meetings. 

First, set the right expectations by briefing the employees on the purpose of the next skip-level meeting. Avoid abstract “we’ll talk about anything” briefs and pick a few areas to focus on (career, operations, personal development, company guidance, etc.). Your employees will appreciate transparency and won’t feel confused or anxious before the meeting. 

Next, send a list of preliminary questions to gauge how your employees feel and if there’s anything they are interested in. To save you time, use tools that automate the whole process. 

Using Geekbot, you can automatically send a list of preliminary questions to your employees directly in Slack or MS Teams. Try our Monthly 1-on-1 Template!

Geekbot will send employee replies to you, and you can quickly plan out the meeting, taking into account employee feedback.

Below are a few example questions Geekbot sends by default:

You can edit these questions or add any other questions you want. 

Note: If you’re having a skip-level meeting with an entire team, consider running an anonymous survey to get more candid feedback before the actual meeting starts. 

2. Build Rapport

You need to be aware of the power imbalance that employees might be feeling when talking to senior leadership. The management gap can make employees feel anxious and less inclined to discuss pressing issues openly.

Here are a few tips to set the right tone during your skip-level meetings from the start:

• Learn a person’s background. Learn a bit about the work that an employee has done so far and make sure they know you know about their latest achievements. 
• Start with an icebreaker. Set people at ease by discussing something non-related to work. 
• Follow-up. If that’s not the first time you are having a skip-level meeting with this employee, ask how things have been going since your last conversation. \

3. Take Notes

For a number of reasons, taking notes is one of the simplest ways of maximizing the value of skip-level meetings.

First, taking notes ensures continuity. Skip-level meetings are being run yearly or quarterly, so there’s no way of remembering what was discussed in the last meeting. For example, if you discussed with an employee a certain project, you can follow up on how that project turned out after a few months. 

Second, you can organize notes from different meetings with different employees and spot certain patterns. If several employees hinted at inefficient project management, you will have written proof that’s not a coincidence.

Third reason is employee loyalty. Meeting notes help you better remember discussions with employees and build deeper rapport with them over time. Employees appreciate when managers follow up on things discussed in the past, both work-related and personal, and feel heard. 

To make a habit of taking notes during skip-level meetings, use tools that suggest taking notes during and right after the meeting. 

As an example, Geekbot’s Meeting Notes will send you questions about the meeting in Slack/MS Teams to aid in keeping track of the notes.

 Geekbot will also automatically organize all the notes in the Slack channel for future reference. 

Recommended Read: How To Take Meetings Notes Faster And More Efficient

4. Wrap Up

At the end of the skip-level meeting, offer a quick summary. Discuss main takeaways and share your notes to see if maybe you sipped something.

Skip-level meetings don’t necessarily have to facilitate some immediate action, but feel free to update your todo-list with actions you want to follow up on.

At the end of the meeting make notes of what you could follow up on during the next meeting. 

Questions For Skip-Level Meetings

Below are some questions you can use during your skip-level meetings. Pick the ones you’re most comfortable with discussing. 

Skip-level meeting questions for employees to ask:

1. What’s currently the main challenge within the company?
2. How could I better align my professional experience with company goals?
3. What would you like to know more about my work?
4. Are there any changes that the company will be undergoing that you can share with me?
5. What has improved in our company in the last 1 year, 5 years?
6. Is the company moving in the right direction?
7. Can you share any advice for my department?
8. What was the most unexpected work challenge for you to deal with in the last year?
9. What are currently the main company’s priorities?
10. What support can I provide for my manager and my team?
11. What metrics do you use to track a company’s success?
12. What skills can I focus on developing to grow in our company?
13. How does the company plan to adapt to recent industry trends or changes?
14. Can you provide insight into the long-term vision and strategy of the company?
15. In what ways can I contribute to the company’s innovation or improvement efforts?
16. How does my role impact the company’s overall success?
17. What leadership qualities are most valued in this organization?
18. Are there new markets or sectors the company is considering exploring?
19. How does the company support continuous learning and professional development?
20. In what ways can I get more involved in cross-departmental projects or initiatives?
21. How does the company evaluate and manage risk in its strategic planning?
22. Can you share a success story from another department that might inspire our team?
23. What are the biggest obstacles currently facing our department, and how can I help address them?
24. How does the company plan to enhance its competitive edge in the coming years?
25. What initiatives does the company have in place to promote employee wellbeing and job satisfaction?

Skip-level meeting questions for managers to ask:

1. Is there anything you would like to ask me?
2. Is there anything your team excels at?
3. What are your biggest concerns or worries?
4. To be successful in your job, what do you need to have more of?
5. Are you receiving adequate feedback?
6. Do you have access to enough resources to succeed?
7. What team members deserve recognition?
8. How did you become involved with a project/hobby / team?
9. How do you enjoy spending time with your family?
10. Are you able to maintain a work-life balance? 
11. Are you feeling overwhelmed with work lately?
12. Which professional goals do you have for the upcoming year?
13. Have you been doing anything new outside of work lately?
14. In your opinion, what is the most important process that needs to be fixed?
15. In your role, what have you observed that I might not be seeing?
16. What is your opinion of working in our company?
17. How do you feel about the current communication channels within our organization?
18. Can you share an instance where you felt exceptionally supported by your team or management?
19. What’s one thing we could change about the workplace to enhance your productivity?
20. How do you view your career progression within our company, and how can we assist in achieving your aspirations?
21. Are there any company policies that you feel could be improved or revised?
22. What’s your perspective on the team dynamics and how they affect your work?
23. How do you think we can foster more innovation and creativity within the team?
24. Is there a particular skill or area of expertise you wish to develop, and how can we support that?
25. What do you enjoy most about your role, and what aspects do you find most challenging?
26. How can we improve in recognizing and addressing employee concerns promptly?
27. Can you suggest any training or development programs that would benefit you or your team?

What Not to Do During Skip-Level Meeting?

Certain ideas and misconceptions about skip-level meetings will quickly turn them into an emotional drain or pointless routine, which are largely negative experiences for both parties.

Employees might feel like the skip meetings are useless and pretentious, while executives might never learn about the realities of the inner workings of their company. 

To avoid never, employees never do these things during skip-level meetings:

• Never seek promotions.

• Never spy on colleagues.

• Never criticize your immediate management. 

• Never attribute blame.

Managers, in turn, should never:

• Never get insulted by someone’s honesty.

• Never treat skip-level meetings as a formality.

• Never encourage employees to criticize peers or spy on them. 

If you want to maximize the efficiency of your skip-level meetings, better preparation goes a long way. 

Use Geekbot to send a list of preliminary questions to your employees before the meeting starts to learn what their struggles are and what you can help with.

Setting up a Geekbot takes only a minute, and the bot will be sending prep questions on autopilot to save you hours on preparations. 
Join the likes of Gitlab, Shopify, and Github that also use Geekbot for running ultra-efficient asynchronous meetings and surveys directly in their favorite team messengers. Try Geekbot for free now!