How to Have a Great Skip-Level Meeting (+20 Questions)

  • 2024-08-07
  • Serra Ardem
How to Have a Great Skip-Level Meeting (+20 Questions)

Open dialogue is crucial in today’s workplace, especially for younger employees like Gen Z who prioritize meaningful engagement with leadership. Skip-level meetings are an effective way to show employees they are valued, encouraging them to participate in shaping the company’s future.

In this blog, we will:

  • Explain what a skip-level meeting is and highlight its benefits
  • Share how to conduct a skip-level meeting as a manager
  • Provide guidance on how to have a productive skip-level meeting as an employee
  • List 20 powerful questions that can be asked during skip-level meetings

Let’s get started.

What is a skip-level meeting?

A skip-level meeting is a one-on-one meeting between an employee and their manager’s manager. In other words, the employee bypasses their immediate supervisor to share their perspectives within the upper management.

Two women around a table laughing and taking notes.

The purpose of skip-level meetings is to foster open communication across different levels of the organizational hierarchy. While senior managers can gather insights from the ground level, employees will feel empowered to voice their opinions directly to upper management.

The frequency of skip-level meetings can change according to organizational size, structure, and leadership style. Holding these meetings quarterly is a good starting point, but more frequent meetings may be beneficial in rapidly changing work environments. Ultimately, ideal frequency should be determined by the organization’s specific needs.

5 Key Benefits of Skip-Level Meetings

Now let’s quickly take a look at the benefits these meetings offer to the employees, managers, and the whole organization.

A skip-level meeting:

  • Makes employees feel heard and valued. This fosters transparency and connection, which contributes to a strong company culture.
  • Is a chance to detect potential problems and prevent escalation. Employees on the front lines often have firsthand knowledge of operational difficulties or customer concerns.
  • Allows senior leaders identify high-potential employees. By observing employees’ problem-solving skills and leadership qualities, managers can spot talent that might otherwise go unnoticed.
  • Nurtures a culture of innovation. Skip-level meetings provide a safe space for employees to propose new ideas, challenge the status quo, and offer creative solutions to problems.
  • Aligns employees with organizational goals. By communicating company strategies and priorities directly to employees, senior leaders can promote a sense of shared purpose.
Two women having a conversation during a skip-level meeting.

How to Run a Skip-Level Meeting as a Manager

Planning and executing a skip-level meeting as a manager requires careful preparation, an open yet professional approach, and close follow-up. Here are the steps you can take before, during and after the meeting to make the most of it.

Before the Meeting

  • Research the employee. Familiarize yourself with their role, projects, and recent performance reviews.
  • Prepare open-ended questions. Make sure they can lead to thoughtful responses and help you delve deeper into the employee’s perspectives. (More on that in the final section.)
  • Communicate the purpose of the meeting and share the agenda. Clearly explain skip-level meeting objectives and send the agenda with the invite to emphasize what you’ll cover.
  • For face-to-face meetings, create a comfortable environment. Choose a private and quiet location for a relaxed, distraction-free atmosphere.
  • For virtual meetings, test your equipment. Verify that you have a stable internet connection, clear audio, and a professional video background.
A man and a woman having a virtual meeting.

During the Meeting

  • Start with casual conversation. Begin the meeting with some informal chat to ease any nervousness.
  • Give the employee your full attention. Maintain eye contact, and do not check your phone or computer during the discussion.
  • Record the meeting and take brief notes. This will help you recall specific issues and provide a reference for follow-up actions.
  • Ask your open-ended questions. Encourage the employee to elaborate on their experiences and share their thoughts on the organization.
  • Provide feedback and guidance. Highlight strengths and areas of improvement, and give practical advice to address any issues raised.

After the Meeting

  • Transcribe the meeting. Convert the meeting to text with AI to ensure accuracy and completeness for reference and follow-up.
  • Summarize key points. Emphasize main takeaways and important insights to guide future actions.
  • Share action items. Clearly outline any tasks or actions that were agreed upon during the meeting and communicate them to relevant parties.
  • Evaluate the meeting. Send a form to the employee to gather feedback and use it to optimize future skip-level meetings.
  • Follow up with the employee. Review progress on action items together and keep the lines of communication open.
A bullet list titled "Open Projects".

How to Have a Skip-Level Meeting as an Employee

A skip-level meeting is a valuable chance for an employee, as it provides direct access to senior leadership and a platform to discuss career aspirations. The following tips can help you navigate the meeting with confidence and seize the opportunity to advance your career.

Before the Meeting

  • Outline the topics and questions you want to discuss. Determine what you hope to achieve from the skip-level meeting, such as feedback, guidance, or support.
  • Practice your pitch. Rehearse what you want to say in a clear and concise way.
  • Review company updates. Be informed about recent company developments that might impact your discussion.

During the Meeting

  • Listen actively to your manager. Maintain eye contact, nod to show understanding, and avoid interrupting.
  • Ask thoughtful questions. Focus on seeking clarification, gaining insights into the company’s direction, or understanding career development paths.
  • Be professional. Avoid jargon or overly complex language, and show genuine interest in your work and the company.
A young woman talking during a virtual meeting.

After the Meeting

  • Send a thank-you email promptly. Express your gratitude for your manager’s time and insights.
  • Implement the feedback you received. Develop a plan for incorporating it into your work 
  • Maintain the relationship. Continue to engage with the senior manager periodically to build a strong professional connection.

20 Powerful Skip-Level Meeting Questions

For both managers and employees, the right skip-level meeting questions can lead to better insights, actionable feedback, and stronger professional relationships. Let’s check 20 powerful questions that managers and employees can ask during skip-level meetings.

Skip-Level Meeting Questions to Ask Employees

  • What are the biggest challenges you’re facing in your role right now?
  • How do you feel about the feedback and recognition you receive?
  • Do you feel you have the necessary resources and support to succeed?
  • Are there any opportunities for growth or development you’d like to explore?
  • How is the team morale? Are there any issues affecting team performance?
  • What do you think could be improved about the company culture?
  • Are there any company policies or procedures that you find ineffective?
  • Do you have any suggestions for improving processes or efficiency?
  • Which tools or technologies do you find most useful, and are there any you’d like to see implemented?
  • How do you perceive the current approach to diversity and inclusion within the company?
White question mark icons on blue surface.

Skip-Level Meeting Questions to Ask Managers

  • What are the KPIs (key performance indicators) for my role, and how am I progressing towards them?
  • Can you give me feedback on my recent projects? What are my strengths and areas of improvement?
  • What kind of feedback do you receive from other departments about my work?
  • Are there any upcoming projects or initiatives where I can contribute or take on more responsibility?
  • What opportunities for growth and development do you see for me in the company?
  • What is your vision for our team’s growth and development?
  • How effective is our team collaboration, and what can be improved?
  • What are the most critical challenges facing our team, and how can I contribute to overcoming them?
  • How is the company adapting to industry trends and challenges?
  • What qualities and skills are you looking for in future leaders within the company?

Frequently Asked Questions

Who initiates a skip-level meeting?

Typically, a manager’s manager (or a higher-level executive) initiates a skip-level meeting. However, an employee can also request a skip-level meeting if they have a concern that hasn’t been addressed by their direct manager, or they want to discuss career goals and opportunities.

Are skip-level meetings confidential?

Yes, skip-level meetings are confidential ideally. If you’re a manager, you can explicitly state that the conversation is confidential at the beginning of the meeting. Avoid sharing specific information about the employee with anyone else unless it’s necessary and with the employee’s consent.

What is the role of HR in skip-level meetings?

HR professionals play various roles in skip-level meetings. They can emphasize the importance of these meetings to both managers and employees, and offer practical guidance on how to conduct them. They can also participate in certain cases, such as then their expertise is required in the meeting. Lastly, they can track the impact of skip-level meetings on employee engagement and performance.

How do I send an invite for a skip-level meeting?

When sending an email invitation for a skip-level meeting, make sure the subject line is clear and concise. Include date, time, duration, location (in-person or virtual) of the meeting, and briefly explain its purpose. Outline the meeting agenda to set expectations, and use a friendly yet professional tone.

What are the outcomes of skip-level meetings?

Skip-level meetings can build trust between employees and senior leadership by breaking down hierarchical barriers and paving the way for open dialogue. Moreover, they can improve the decision-making processes, as they enable managers to gather diverse viewpoints. A skip-level meeting can also align an employee with company goals, clarifying how their role supports the larger strategy.

Summary

This blog shared actionable skip-level meeting tips for both managers and employees. It also listed 20 powerful questions that can be asked during these meetings, which can improve communication significantly and drive better results.

Before concluding, let’s recap the best practices for successful skip-level meetings:

  • Whether you’re a manager or employee, ask thoughtful questions to facilitate meaningful discussion and gain valuable insights.
  • Leverage technology, such as an AI-powered transcription service, to accurately capture meeting content and document important conversations.
  • Whether in-person or virtual, ensure that the meeting space is comfortable, so participants can feel at ease and communicate effectively.
  • Follow up on action items and key takeaways after the meeting to implement changes and maintain momentum towards achieving goals.
  • If you’re a manager, collect feedback from employees to optimize future skip-level meetings.

By adopting these tips, both parties of the meeting can support each other and contribute to a more transparent, collaborative work environment.

Serra Ardem

About Serra Ardem

Serra Ardem is a freelance writer and editor based in Istanbul. For the last 8 years, she has been collaborating with brands and businesses to tell their unique story and develop their verbal identity.