Skip Level Meeting Questions to Ask Employees
Build trust and gather honest feedback with these strategic questions that help you understand team dynamics, identify issues, and strengthen your leadership.
1How would you describe the current team dynamic?
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How would you describe the current team dynamic?
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Why this works
Opens discussion about team culture and relationships without being confrontational, revealing potential issues or strengths.
2What's working really well in your role right now?
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What's working really well in your role right now?
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Why this works
Starts positive and helps identify successful practices that can be replicated across the team.
3If you could change one thing about how we work, what would it be?
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If you could change one thing about how we work, what would it be?
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Why this works
Gets specific feedback about processes or policies in a constructive way that invites solutions.
4How do you feel about the communication flow in the team?
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How do you feel about the communication flow in the team?
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Why this works
Reveals potential communication gaps or successes that directly impact productivity and morale.
5What support do you need to be more effective in your role?
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What support do you need to be more effective in your role?
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Why this works
Identifies resource gaps, training needs, or obstacles that might be limiting their performance.
6How would you describe your relationship with your direct manager?
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How would you describe your relationship with your direct manager?
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Why this works
Gathers feedback about management effectiveness and identifies potential issues in the reporting structure.
7What's the biggest challenge you're facing right now?
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What's the biggest challenge you're facing right now?
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Why this works
Reveals current pain points and obstacles that might not be visible from a higher level.
8How do you feel about the direction the team is heading?
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How do you feel about the direction the team is heading?
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Why this works
Gauges alignment with team goals and reveals any concerns about strategy or priorities.
9What would make you more excited about coming to work?
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What would make you more excited about coming to work?
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Why this works
Identifies motivational factors and engagement opportunities that can improve job satisfaction.
10How do you think we could improve collaboration across the team?
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How do you think we could improve collaboration across the team?
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Why this works
Gets specific suggestions for improving teamwork and reveals collaboration challenges.
11What's something you wish leadership knew about your work?
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What's something you wish leadership knew about your work?
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Why this works
Opens up communication about their contributions and any concerns they want leadership to understand.
12How do you feel about the feedback you receive?
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How do you feel about the feedback you receive?
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Why this works
Assesses the effectiveness of current feedback systems and identifies areas for improvement.
13What opportunities do you see for growth in your role?
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What opportunities do you see for growth in your role?
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Why this works
Reveals their career aspirations and helps identify development opportunities that benefit both them and the organization.
14How do you think we could better recognize good work?
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How do you think we could better recognize good work?
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Why this works
Gets input on recognition preferences and reveals any gaps in current appreciation systems.
15What's the most frustrating part of your job right now?
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What's the most frustrating part of your job right now?
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Why this works
Identifies specific pain points that might be affecting productivity or job satisfaction.
16How do you feel about the workload and priorities?
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How do you feel about the workload and priorities?
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Why this works
Assesses work-life balance and priority alignment, revealing potential overwork or misalignment issues.
17What would help you feel more connected to the company's mission?
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What would help you feel more connected to the company's mission?
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Why this works
Gauges engagement with company values and identifies ways to strengthen mission alignment.
18How do you think we could improve decision-making processes?
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How do you think we could improve decision-making processes?
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Why this works
Gets feedback on organizational processes and reveals potential bottlenecks or inefficiencies.
19What's something you're proud of accomplishing recently?
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What's something you're proud of accomplishing recently?
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Why this works
Celebrates their achievements and helps identify successful practices or contributions.
20How can I better support you and your team?
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How can I better support you and your team?
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Why this works
Directly asks for their input on leadership support and creates an open channel for ongoing feedback.
Best Practices for Skip Level Meetings
Expert tips and techniques for getting the most out of these questions.
Best Practices
Create Psychological Safety
Start with positive questions and assure confidentiality. Make it clear that honest feedback is valued and won't be held against them.
Listen More Than You Talk
Use the 80/20 rule - let them do 80% of the talking. Your role is to listen, understand, and gather insights.
Follow Up on Feedback
When you receive actionable feedback, follow up to show you're taking it seriously. This builds trust for future conversations.
Question Sequences
The Trust Building Sequence
The Problem Identification Sequence
Common Pitfalls
Don't Make It About Their Manager
Avoid questions that could create conflict between the employee and their direct manager. Focus on systems and processes instead.
Don't Promise Immediate Changes
Be honest about what you can and cannot change. Overpromising can damage trust if you can't deliver.
Don't Ignore Confidentiality
Never share specific feedback with their manager without permission. This destroys trust and prevents honest future conversations.