Skip-Level Meeting Questions: 30 Examples

Skip-level meetings give senior leaders a direct line to the people two levels down, surfacing feedback about managers and team health that rarely travels up on its own. The 30 skip-level meeting questions below are organized by category, from work priorities to manager effectiveness to career growth, so you can run a conversation that builds trust instead of feeling like an audit.

What Are Skip-Level Meeting Questions?

Skip-level meeting questions are prompts a senior leader uses when meeting 1:1 with employees who don’t report to them, bypassing a management layer. The goal is to surface feedback about team health, manager effectiveness, and culture that might not travel up the chain on its own.

Category	Goal	Questions
Work and priorities	Establish context, check alignment	1-5
Manager effectiveness	Surface upward feedback	6-10
Team culture	Spot health issues early	11-15
Career and growth	Identify retention risk	16-20
Company alignment	Test strategy communication	21-25
Closing	Normalize ongoing dialogue	26-30

Questions About Work and Priorities

These questions establish context: what the employee is working on, how aligned they feel, and whether priorities are clear. They are non-threatening starting points that build rapport before more sensitive topics, and reveal whether strategic decisions are being communicated consistently across management layers.

What’s taking up most of your time right now?
Is there anything you’re working on that you’re not sure is the right priority?
What’s one thing we could stop doing that would free up your time?
Where do you feel your work has the most impact?
Are there areas where you feel unclear on what “good” looks like?

Questions About Manager Effectiveness

Skip-level meetings are one of the few places to collect upward feedback on managers outside a formal review cycle. Look for patterns across conversations, not individual complaints. According to Gallup, managers account for 70% of the variance in employee engagement, and 57% of employees have left a job specifically because of their manager.

Pair these insights with data from structured peer feedback to get the full picture.

Do you feel your manager helps you grow professionally?
Does your manager give you clear, actionable feedback?
Do you feel comfortable raising concerns or disagreements with your manager?
What’s one thing your manager does really well?
Is there anything you wish your manager did differently?

Questions About Team Culture

Culture questions surface whether the team environment is psychologically safe, collaborative, and fairly structured. They are especially useful after a reorganization, leadership change, or period of rapid growth when norms are still settling. Look for consistent patterns across multiple conversations before drawing conclusions.

Do you feel like people are treated fairly on your team?
Would you describe your team as collaborative or siloed?
Is there a clear sense of shared purpose on the team?
Are there any tensions on the team that slow down how you work?
Do you feel your ideas and contributions are valued by your teammates?

Questions About Career and Growth

Career development is a top driver of voluntary attrition. Skip-level conversations give employees an additional advocate, particularly for people uncomfortable raising ambitions with their direct manager. Pew Research Center found that lack of advancement opportunities was the second most common reason employees quit their jobs in 2021, behind only low pay.

Do you feel like you’re growing in your role?
Is there a type of work you want more exposure to?
Do you have clarity on what it would take to be promoted?
Are there skills you want to develop that you’re not currently using?
Is there anything blocking your progress that I should know about?

Questions About Company Alignment

These questions reveal whether company strategy is being communicated clearly across levels. If employees don’t understand how their work connects to broader goals, engagement suffers regardless of manager quality. Gallup’s 2024 U.S. engagement data found only 31% of employees were engaged at work, a figure closely tied to poor strategic communication and unclear expectations.

Do you feel like you understand where the company is headed?
Does the company’s direction feel exciting to you right now?
Are there company decisions that have felt unclear or confusing?
Do you feel like your work connects to the company’s goals?
What would you want leadership to know that we might not be hearing?

Questions to Close the Meeting

Closing questions signal that the conversation was valuable and create an opening for ongoing dialogue. They normalize the skip-level relationship and show you are listening rather than auditing. Leave time for these: the most important things are often said last.

Is there anything I should have asked that I didn’t?
What’s one thing you’d change about how we do things here?
Is there anything you need from me as a leader?
Are there people on the team doing excellent work who don’t get enough recognition?
Would it be useful to meet like this again? How often?

How to Run a Skip-Level Meeting

Skip-level meetings work best when they are low-stakes and predictable. Employees should know when to expect them, why they are happening, and what you will do with the information. Most leaders run them quarterly or twice a year. Monthly risks feeling like surveillance; once a year is too infrequent to build trust.

Before the meeting, tell the employee’s manager it is happening. You are not going behind anyone’s back; you are running a normal leadership process. After the meeting, share anonymized themes with the relevant manager, not individual comments. Look for patterns across five or more conversations before acting on any single piece of feedback.

If your team uses Windmill’s 1:1 feature, Windy can help you set prep questions ahead of skip-level meetings and carry action items forward automatically. You can also use the best 1:1 meeting software comparison to find tools that support skip-level workflows.

Frequently Asked Questions

How often should skip-level meetings happen?

Most leaders run skip-level meetings quarterly or twice a year. Monthly risks feeling like surveillance; once a year is too infrequent to build trust or surface real patterns.

Should skip-level meetings be confidential?

Be explicit upfront about what you will and won't share. Most leaders commit to sharing themes with the manager without attributing specific comments to individuals.

How long should a skip-level meeting be?

30 minutes is usually sufficient. Use the first 5 to 10 minutes to set context and build rapport before moving to substantive questions.

What should I do with feedback from skip-level meetings?

Look for patterns across multiple conversations before acting. Share anonymized themes with the relevant manager and follow up in later meetings to see if anything has changed.

What's the difference between a skip-level meeting and a 360 review?

A 360 review is structured, documented, and tied to a performance cycle. A skip-level meeting is informal and happens outside review cycles. It is an ongoing culture and manager-health check, not a formal evaluation.