How to break the hierarchy with a skip level meeting

When you’re a CEO, Vice President, or other C-level exec, it’s common practice to only speak to other managers. This approach means you get distilled information about entire teams from one source — and most of the time, it’s super efficient. 

The downside is that sometimes, valuable information never makes it to the top. And it works both ways: when senior managers have zero contact with frontline staff, the latter often feel cut off from company decisions, which can be demotivating. 

This is where a skip level meeting comes in handy.

A skip level meeting is where a senior manager ‘skips’ down to talk to those a layer or two beneath their line of command. It’s used by small businesses as big organizations alike. Done well, it can be an effective way to solve specific issues and share new ideas. Done poorly, it can be a major source of resentment and chaos. So that’s why we’ve put together this guide to help you get it right. 

What is a skip level meeting?

A skip level meeting is a type of 1+1 or team meeting where employees speak directly with a manager who is one or more levels above their immediate supervisor. Essentially, it involves circumnavigating the usual line of command to share ideas and concerns without the usual formalities. 

This means, for example, that if you report to a team leader, a skip level meeting would have you sit down with the leader of your team leader, e.g. a department head or a senior manager. 

These meetings are designed to bypass the direct line, which sounds sneaky, but actually comes with lots of benefits, including unfiltered feedback, a better understanding of employee concerns, and a stronger connection between upper management and front-line employees. 

Skip level meetings: a real-world example

In a growing tech company, the CEO typically relies on updates from a core leadership team, including the Chief Technical Officer (CTO), Chief Operating Officer (COO), and Chief Marketing Officer (CMO), to understand how different segments of the business are performing.

But even with these insights, the CEO might feel disconnected from the day-to-day operations and all the great ideas bubbling up from the ground level. To get a more direct view, the CEO decides to hold a skip level meeting.

In this scenario, the CEO schedules time with project managers and lead developers, roles that are usually two levels down in the hierarchy and report indirectly through senior management. 

This lets the CEO bypass the filter of upper management and engage directly with those on the frontline. Through these conversations, the CEO can uncover new ideas, address unseen challenges, and better understand the team’s morale, leading to better decision-making on their part, not to mention a team that feels more involved. 

What’s the purpose of a skip level meeting?

The skip level meeting goes beyond just an ordinary catch-up or check-in that you might have with your direct supervisor. 

Direct feedback and insight

It allows upper management to hear directly from employees about their experiences, challenges, and suggestions for improvement without the potential bias or filtering of intermediate supervisors. This direct line of communication can provide leaders with insights that might not be apparent through regular reporting channels.

Employee engagement and morale

By giving employees a platform to voice their concerns and ideas directly to higher-level management, it signals that their opinions are valued and considered important. This can boost morale and engagement by making employees feel heard and appreciated at higher levels of the organization.

Identify issues and opportunities

These meetings can uncover hidden problems or opportunities that may not be visible to upper management or may not have been communicated effectively through normal channels.

Career development

They provide an opportunity for employees to discuss their career aspirations and receive guidance from senior leaders, potentially opening doors for mentorship and growth.

Cultural alignment and reinforcement

Skip level meetings can help reinforce company values and culture by directly engaging with employees, addressing any misalignments, and ensuring that the company’s strategic goals and cultural values are understood and shared across all levels.

Increased transparency

These meetings can foster a culture of openness within the organization. When employees see that their leaders are willing to listen to them directly, it can build trust and demystify the actions and decisions of upper management.

Employee empowerment

Giving employees the opportunity to voice their concerns, ideas, and feedback directly to upper-level management empowers them. It makes them feel valued and can motivate them to be more engaged and proactive in their roles.

Identifying and addressing issues early

Through direct feedback, leaders can identify potential issues and areas for improvement early on. This proactive approach can help in mitigating problems before they escalate, saving resources and fostering a healthier work environment.

Career development and mentorship

Skip level meetings can serve as a platform for discussing career paths, aspirations, and development opportunities. This can be particularly beneficial for employees looking for growth and advancement, as it provides them with visibility and access to senior leadership for guidance and support.

How to prepare for a skip level meeting

Prep involves thoughtful planning and a healthy dose of empathy to keep the conversation comfortable for both parties. Here’s how to approach it. 

Frequency of the meetings

Skip level meetings work best when they’re held on a regular basis. Not only does this give you all of the benefits —  it also helps to normalize the process and integrate it into the organizational culture as a positive measure, rather than a reactionary one.

Preparing the team leader (1-2 weeks before the meeting)

This heads-up helps to manage any potential concerns and ensures the manager understands the constructive purpose of the meeting.

Example email to the team leader:

Hi [Manager’s name],

I hope this message finds you well. I’m reaching out to share that I’ll be conducting a skip level meeting with our [Department/Team name] on [Date]. 

The intention is to directly connect with the team members, gaining insights into their day-to-day experiences, challenges they might be facing, and any ideas they have for improving our work environment. This is part of our ongoing efforts to foster a culture of open communication and continuous improvement.

I value your leadership and the role you play in our team’s success. I’ll ensure to share feedback and insights from the meeting with you afterward, and I’d welcome any thoughts or specific areas you think I should focus on during my discussion with the team.

Thank you for your support and understanding. Let’s catch up soon after the meeting.

Warm regards, [Your name]

Preparing the employees (2-3 days before the meeting)

Informing the relevant employees about the meeting well in advance gives them time to reflect on their experiences and gather their thoughts on what they’d like to share.

Example email to the employees:

Hi team,

On [Date], we’ll be meeting to discuss how things are going. It’s an opportunity for us to connect, and for me to hear more about how you’re doing, and how I’m doing as a leader. I’m eager to hear about your work, any obstacles you’re encountering, and your suggestions for how we can evolve and grow stronger as a team. Your perspectives are incredibly important to the success of our organization, and I’m here to listen and support you.

Please think about any topics or ideas you’d like to discuss. Whether it’s something we’re doing well that you’d like to see more of, or areas where you feel we could improve, your input is important. If there are specific points you’d prefer to discuss one-on-one, feel free to reach out to me directly before our meeting.

Looking forward to our conversation and learning more about your experiences.

Best wishes, [Your name]

By taking these steps, you’re laying the groundwork for a productive skip level meeting that encourages open dialogue and fosters a culture of transparency and continuous improvement.

Typical agenda of a skip level meeting (with tips)

Empathy is key here. As a senior leader, it’s important to remember how nerve-wracking it is speaking to the boss. With that in mind, here’s a general outline for a productive and calm catch-up. 

1. Opening and rapport building

• Greet each participant warmly as they join the meeting and express your genuine appreciation for their time and willingness to participate. 
• Begin with a brief introduction and some check-in questions to set a warm, welcoming tone. 
• Make it clear that this is an opportunity for open conversation and that their honest feedback is valued. 
• Share the purpose of the skip level meeting, emphasizing it’s a chance for open conversation and feedback.
• Ensure confidentiality where necessary and appropriate. Let participants know that their feedback will be used constructively and that you’re there to support their success and address any concerns they have. 
• Take detailed notes or, with permission, record the meeting for later review. This helps you remember the meeting and take action, while showing the employee they’re being taken seriously. 

2. Review of the employee’s role and recent achievements

• Ask the employee to describe their current projects and highlight any recent successes. This not only acknowledges their contributions but also provides context for the discussion.
• If you use project management software (and we highly recommend it), bring in stats to make the conversation that little bit more objective. 

3. Discussion on challenges and support

• Invite the employee to share any challenges they are facing in their role.
• Discuss what support they need, whether it’s resources, training, or something else.
• Use a mix of direct and reflective questions to encourage discussion. 

Example questions: 

• “Can you share an example of a time you felt particularly proud of our team’s work? What made that moment stand out?”
• “What barriers are currently preventing you from doing your best work, and how can we address them?”
• “How do you perceive our company culture, and what changes would you suggest to strengthen it?”

4. Feedback on management and company culture

• Seek the employee’s perspective on their direct management and overall company culture.
• Ask for insights into leadership effectiveness and morale.
• The ‘start, stop, keep’ method is useful here. This involves asking participants what practices or behaviors they believe the organization or leadership should start doing, stop doing, and keep doing. This framework can make it easier for employees to articulate their thoughts and for leaders to action them.

Example questions:

• “What is one thing you believe our team should start doing to improve our work environment?”
• “Is there a process or habit we should stop because it hinders our productivity or morale?”
• “What’s something we’re currently doing well that you think we should continue doing?”

5. Ideas for improvement and innovation

• Encourage the employee to share their ideas for improvements or innovations within their team or the broader organization. 
• Practice empathetic active listening to encourage openness. 
• Ask open-ended questions that require more than a yes or no answer. Questions like “How do you feel about the current project management process?” or “What improvements would you suggest for team communication?” prompt detailed responses and deeper insights.
• Use the Socratic method. Instead of seeking answers or solutions directly, this method encourages a deeper exploration of the topics discussed, helping uncover underlying issues or opportunities that might not be immediately apparent.

Example questions:

• “Why do you think this challenge persists, and what underlying factors contribute to it?”
• “How does this process align with our overall goals, and where do you see discrepancies?”

6. Career aspirations and development

• Discuss the employee’s career goals and potential growth opportunities.
• Offer guidance or mentorship on achieving their aspirations.

7. Closing and next steps

• Summarize key points from the conversation and any agreed-upon actions.
• Express appreciation for the employee’s openness and contributions.
• Outline the next steps, including how you’ll address feedback and any follow-up meetings.
• Based on the feedback and discussions during the meeting, create an action plan. Prioritize each action, assign tasks, and set a timeline for completion. 
• Close the feedback loop by sharing updates on progress and changes made as a result of the skip level meetings. This can be done in team meetings, through company newsletters, or direct emails. Sharing these updates reinforces the value of the skip level meetings and encourages ongoing engagement and feedback.

Common pitfalls (and tips on how to avoid them)

Skip levels can be a great way to uncover valuable insights. But they’re not without their challenges. Here are some of the top hurdles to look out for.

Not preparing participants enough 

A lack of prep usually leads to unproductive meetings. Participants might not be sure what to expect, which can additionally cause anxiety or reluctance to speak openly.

Tip: Ensure both the team leader and the employees are well-prepared. Provide a clear kickoff agenda and communicate the meeting’s purpose well in advance. This preparation will help participants feel more comfortable and encourage a more open conversation.

Allowing managers to feel threatened

Skip level meetings can sometimes make direct managers feel bypassed or threatened, particularly if they’re not properly informed or involved in the process.

Tip: Involve managers in the planning process and reassure them of the meetings’ objectives. Explain how these meetings provide valuable insights that benefit the team and the organization as a whole. Sharing positive feedback and outcomes with managers can also help alleviate any concerns.

Failing to follow up

Without visible action, employees might feel their feedback is ignored, which can lead to disillusionment.

Tip: Always follow up on the feedback received during these meetings. Communicate what actions will be taken, and provide updates on progress. This follow-through demonstrates that you value their input and are committed to making positive changes.

Dominating the conversation

The meeting should primarily be about listening to employees. Dominating the conversation can prevent the gathering of valuable insights.

Tip: Focus on listening and ask open-ended questions to encourage employees to share their thoughts. Resist the urge to fill silences with more talking; instead, give participants time to formulate their ideas.

Overlooking confidentiality

Employees may share sensitive information during these meetings. Failing to handle this information discreetly can breach trust.

Tip: Assure participants of confidentiality right from the start. When sharing insights from the meeting with others, focus on general themes rather than specific comments, especially if they could be sensitive.

Not acting on feedback

Similar to failing to follow up, not acting on the feedback provided can make employees feel their input is not genuinely valued.

Tip: Prioritize actionable feedback and create a plan for addressing it. Keep employees informed about how their feedback is influencing changes or decisions within the organization.

Alternatives to skip level meetings 

While skip level meetings are great for gathering insights and strengthening connections, there are other strategies available. They don’t offer quite the same thing, but they’re good alternatives (or supplementary methods).

1. Anonymous feedback tools: Some digital platforms allow employees to submit feedback anonymously. This can be highly effective in encouraging candid responses, especially on sensitive issues.

2. Regular employee surveys: Design surveys to assess satisfaction, engagement, and collect suggestions for improvement across the organization. When sent out regularly, they provide a continuous stream of data while ensuring every voice has the chance to be heard.

3. Town hall meetings: These larger, open forums allow senior leaders to address the entire organization or large departments at once. They’re useful for communicating strategic decisions and collecting broad feedback, although they may not be as effective for deep, individualized insights.

4. Focus groups: Small, topic-specific focus groups can provide detailed feedback on specific areas of concern or interest. This format encourages in-depth discussion and can be particularly useful for exploring new initiatives or addressing complex challenges.

5. 360-degree feedback: This involves collecting insights about an employee from their manager, peers, and direct reports. It can be adapted for leadership roles to gather feedback about senior leaders from various levels within the organization.

6. Mentoring programs: Implementing mentoring programs can foster direct lines of communication between senior leaders and employees at different levels. While primarily aimed at professional development, these relationships can give leaders insights into employee experiences and concerns.

7. Open office hours: Senior leaders can set aside regular times when they’re available for any employee to drop in and discuss ideas, concerns, or feedback. This approach signals openness and accessibility, though it may not reach as many employees as some other methods.

Project management tools were made for skip level meetings 

Project management tools aren’t just for tracking tasks. By offering a clear view of the team’s achievements, they keep conversations grounded in real data, setting the stage for a productive chat. Plus, with Backlog, you can use task tracking, burndown charts and Gantt charts to action all those post-meeting points and keep the team in-the-loop. 

So, as you gear up for your next skip level meeting, lean on these tools to guide the conversation, making every meeting not just a chat, but a step forward for your team and projects.