Skip Level Meetings: Manager How-To Guide

Skip level meetings are a powerful tool for managers to connect with team members two levels below them, bypassing the immediate supervisor. They build trust, surface hidden issues, and give you a clearer picture of the organization’s health beyond filtered reports. This guide walks you through planning, running, and following up on these meetings so they are productive and comfortable for everyone.

What You’ll Need

• A calendar invite with a clear agenda and purpose
• A private, quiet space (virtual or in-person) free from interruptions
• Your active listening skills and an open, non-defensive mindset
• A notetaking method (digital or paper) to capture key points and action items
• A follow-up plan to track commitments and communicate outcomes

Step-by-Step

1. Set the purpose and frequency. Decide why you are holding these meetings: to understand employee sentiment, identify blockers, develop talent, or improve communication. Typically, hold them quarterly or bi-monthly, and be consistent so employees know what to expect.
2. Schedule with the employee, not through their manager. Send the invite directly to the employee, but loop in their manager as a courtesy. Choose a time that does not conflict with their key deliverables or personal commitments.
3. Prepare a simple agenda and share it in advance. Keep it light: “A casual conversation about your work, challenges, and ideas.” Include a few open-ended questions like “What is going well?” and “What could be better?” so they can think ahead.
4. Start with rapport and clear intent. Open by saying, “This is a safe space to speak openly. Nothing you say will be held against you, and I won’t share specifics with your manager without your permission.” Then ask a simple icebreaker about their week or a project they are excited about.
5. Listen more than you talk. Aim for an 80/20 listening-to-talking ratio. Use prompts like “Tell me more about that” and “How does that affect your day-to-day?” Resist the urge to jump in with solutions or defend decisions.
6. Ask about the manager relationship. Gently probe: “How is communication with your manager?” “What support do you need from them?” Frame it as improving teamwork, not evaluating the manager. Avoid leading questions that assume problems.
7. Explore systemic issues. Ask about processes, tools, or cross-team collaboration. For example: “What slows you down?” “If you could change one thing about how we work, what would it be?” These insights can reveal organizational friction.
8. Discuss development and aspirations. Ask about their career goals and what skills they want to build. This shows you care about their growth, not just their output. Offer guidance or resources if appropriate.
9. Wrap up with thanks and next steps. Summarize what you heard, thank them for their honesty, and clarify any immediate actions. For example, “I’ll look into the software request and update you within two weeks.”
10. Follow through and follow up. After the meeting, send a brief summary to the employee, and if they agreed, share relevant insights with their manager (without attributing sensitive comments). Track action items and check back on them at the next meeting.

Common Mistakes

• Making it a performance review. Skip level meetings are not for evaluating the employee or their manager. Keep the focus on experience and support.
• Talking too much. If you dominate the conversation, you learn nothing. Silence is okay; let them fill it.
• Promising confidentiality you cannot keep. Be honest about what you will share. If they raise a serious issue, you may need to escalate it, so say that upfront.
• Ignoring the direct manager. Skipping the manager entirely can create distrust. Always keep them informed (without breaking confidences) and avoid undermining their authority.
• Acting on every complaint. Not every issue requires immediate action. Sometimes employees just need to vent. Overreacting can make things worse.
• Being defensive. If they criticize a decision you made, do not argue. Thank them for the feedback and explore their perspective.

Tips

• Use the same questions each time. This creates a baseline and makes it easier to spot trends over time.
• Meet outside the office. A coffee shop or a walk can feel less intimidating than a conference room. Virtual meetings are fine too, but keep the camera on to build connection.
• Take notes, but not verbatim. Write down themes and action items, not every word. This keeps the conversation natural.
• Follow up on previous action items. If you promised to do something, show you did it. This builds trust and shows the meeting matters.
• Be aware of power dynamics. The employee may be nervous. Reassure them that honesty is valued, and avoid punishing candor.

Troubleshooting

What if the employee is silent or gives one-word answers? Use more specific, open-ended questions like “What is the most frustrating part of your week?” or “Tell me about a recent win.” Try sharing a small vulnerability about yourself to model openness.

What if they complain about their direct manager? Stay neutral. Do not agree or disagree. Ask clarifying questions like “What would better support look like?” Then, with the employee’s permission, discuss the issue with the manager as a coaching opportunity, not a complaint.

What if they bring up sensitive topics like burnout or harassment? Take it seriously. Thank them for sharing, and if it is a policy violation, explain that you must escalate it to HR. Do not promise to keep it secret.

What if the manager feels threatened? Reassure the manager that the goal is to improve team health, not to spy on them. Share general themes (e.g., “the team wants more recognition”) without attributing to individuals.

What if you cannot solve the issue they raise? Be honest about what you can and cannot do. Offer to connect them with the right person. Sometimes just being heard is enough.

Frequently Asked Questions

How often should skip level meetings happen? Quarterly is a good default. More frequent (monthly) can be useful for new hires or during major changes, but too often can feel like surveillance.

Should I meet with every team member individually? Ideally yes, but if you have a large organization, prioritize new hires, high-potentials, and those in critical roles. Rotate through the rest over time.

What if the employee is too nervous to speak openly? Build trust gradually. Start with low-stakes questions, and do not push. Offer to meet again in a few weeks. Sometimes a second meeting is more productive.

How do I avoid undermining the direct manager? Always frame the conversation as “how can we support you and your manager?” Never criticize the manager directly, and loop them in on general themes (with permission).

What should I do with the information I gather? Look for patterns across multiple meetings. If several people mention the same issue, that is a systemic problem worth addressing. For individual concerns, act only if the employee asks you to or if it is a policy issue.

Can skip level meetings replace one-on-ones? No. They are complementary. One-on-ones with the direct manager are essential for day-to-day support and performance. Skip levels are for broader organizational insight.

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