You're about to meet with your manager's direct report. You want honest feedback about what's really happening on the front lines. But you also don't want to undermine their manager or make them feel like they're being interrogated.
Skip-level meetings can build organizational trust and surface insights that would never reach you otherwise. Or they can create suspicion, erode middle management relationships, and make employees feel caught between layers of leadership.
The difference comes down to the questions you ask and how you ask them.
This guide provides the specific skip-level meeting questions that work, organized by purpose and context. You'll also learn the questions you should never ask—and why they backfire.
TL;DR
- Skip-level meetings uncover insights that won't surface through normal reporting chains
- Start with 5-8 trust-building questions in your first skip-level, not 50 diagnostic ones
- Never ask employees to directly critique their manager—it puts them in an impossible position
- Focus on listening (80%) over talking (20%)
- Follow up visibly on feedback or trust disappears quickly
- Regular cadence matters—tools like Bettermeets help maintain consistency without pressure
What You'll Learn
- What skip-level meetings are (and critical misconceptions to avoid)
- How to set the right tone before asking any questions
- The 8 best questions for your first skip-level meeting
- 40+ questions organized by purpose: trust-building, team dynamics, manager feedback, strategic alignment
- Questions you should never ask (and better alternatives)
- The 80/20 listening rule that makes skip-levels effective
- How to follow up and close the loop to maintain trust
What Are Skip-Level Meetings?
A skip-level meeting happens when a senior leader meets directly with employees two or more levels below them on the org chart, without the employee's direct manager present.
For example: A VP meets with individual contributors who report to directors. A director meets with team members who report to managers. The "skip" refers to bypassing at least one management layer.
The Purpose of Skip-Level Meetings
When done well, skip-levels serve several functions:
Get an unfiltered view of the front lines. Information naturally gets filtered as it moves up organizational hierarchies. Some details get lost. Some problems get downplayed. Skip-levels give you direct access to what's actually happening.
Build trust between leadership and individual contributors. When senior leaders invest time listening to people several layers down, it signals that their perspectives matter. This builds engagement and retention.
Identify blind spots in information flow. Are your middle managers accurately representing what their teams experience? Are they aware of problems their teams face? Skip-levels reveal gaps.
Surface issues before they compound. Small problems that go unaddressed become big problems. Regular skip-levels catch issues early when they're still fixable.
Show employees that leadership is accessible. Many employees never interact with senior leaders. Skip-levels break down that barrier and make leadership feel less distant.
Critical Misconception to Address
Here's what skip-level meetings are NOT:
They're not an investigation of your middle managers. They're not performance reviews disguised as conversations. They're not complaint sessions. They're not opportunities to go around your direct reports.
Done poorly, skip-levels undermine middle managers and create an environment of suspicion. Done well, they strengthen your entire management chain by giving you context to coach your direct reports more effectively and surface systemic issues that need addressing.
When to Conduct Skip-Level Meetings
Regular cadence (quarterly): For established teams where things are stable. Maintains connection without overwhelming anyone's calendar.
Monthly during change: When the organization is going through major transitions—restructuring, leadership changes, market shifts. More frequent touchpoints help you understand impact.
After major milestones: Post-launch, after big projects complete, following significant company events. Captures lessons learned while they're fresh.
When sensing disconnect: If you suspect information isn't flowing accurately up the chain, or if engagement scores drop unexpectedly.
Setting the Right Tone Before Asking Questions
The power dynamic in skip-level meetings creates inherent tension. Employees meeting with their boss's boss (or higher) often feel nervous. Many won't speak candidly unless you actively create psychological safety.
Here's how to set the right tone before you ask a single question:
1. Communicate Transparently Beforehand
Send an invitation email that explains:
The purpose: "I'm meeting with team members across the organization to learn more about what's working well and where we can improve. This is about building connections and understanding, not investigating anyone."
What you'll discuss: Share 2-3 example questions so there are no surprises.
Confidentiality: Be explicit about what you will and won't share. "Our conversation is confidential. I'll look for themes across multiple meetings that can help us improve, but I won't share who said what with your manager or anyone else."
Optional attendance: Making skip-levels mandatory signals "you're in trouble." Instead: "I'd love to hear your perspective, but attendance is completely optional."
2. Brief Middle Managers First
Before conducting skip-levels with their teams, meet with your direct reports (the employees' managers) to explain:
Why you're doing this: "I want to understand how well our strategy is reaching the front lines and where we can support teams better. This helps me be a better coach to you."
What you'll ask about: Share your question list. Transparency prevents paranoia.
How you'll protect confidentiality: "I'll identify themes across meetings, not attribute specific comments to individuals. If something comes up that needs addressing, I'll discuss it with you in terms of patterns, not people."
Get their buy-in. If middle managers feel like you're going around them rather than supporting them, skip-levels create resentment and damage trust.
3. Start Meetings with Rapport, Not Questions
The first 3-5 minutes matter more than you think.
Acknowledge their work: "I've heard great things about your work on [project]. Thank you for taking time to meet with me."
Share something about yourself: Reduce the status gap. "I know these meetings can feel a bit formal. I'm just trying to understand how things are really going and learn from people closer to the work."
State confidentiality again: Even though you sent it in email, repeat it verbally. "Before we start, I want to be clear: what we discuss stays between us. I'm looking for themes to help the organization, not to report back on individuals."
This investment in psychological safety determines whether you get honest insights or polite platitudes.
The 8 Best Questions for Your First Skip-Level
If you're new to skip-level meetings, don't try to ask 50 questions. Start with these 8. They build trust, surface insights, and don't put employees in awkward positions.
1. What's working well in your role or on your team right now?
Why this works: Starts positive. Shows you care about strengths, not just problems. Reveals what to protect and replicate.
What you're listening for: Energy in their voice when they talk about certain aspects. These are areas worth preserving.
2. What's one thing that would make your job easier or more effective?
Why this works: Forward-looking and actionable. Doesn't require criticizing anyone. Often surfaces quick wins you can deliver.
What you're listening for: Process bottlenecks, missing information, tooling gaps, communication issues.
3. When have you felt most proud to be part of this team or company recently?
Why this works: Reveals what motivates them and what's working culturally. Helps you understand what values actually matter to front-line employees.
What you're listening for: Specific moments that made them feel valued or part of something meaningful.
4. What information or context would help you do your job better?
Why this works: Often reveals that strategy isn't translating to the front lines. Communication gaps are common and fixable.
What you're listening for: Gaps between what leadership thinks it's communicating and what employees actually understand.
5. How well do you understand how your work connects to our company goals?
Why this works: Tests if strategic priorities are clear at all levels. Lack of connection is a red flag.
What you're listening for: Can they articulate the link? If not, that's a coaching opportunity for their manager—or a sign that goals aren't clear at any level.
6. What's something you think we should be doing differently as a company?
Why this works: Invites strategic thinking without targeting individuals. Front-line employees often see opportunities leadership misses.
What you're listening for: Ideas you haven't considered. Frustrations with company direction. Competitive insights.
7. Is there anyone on the team doing great work who deserves more recognition?
Why this works: Helps you identify hidden contributors. Shows you value recognition, not just problem-solving. Builds goodwill.
What you're listening for: Names that come up across multiple skip-levels. These are people worth investing in.
8. What questions do you have for me?
Why this works: Makes it genuinely two-way. Their questions reveal what they're uncertain or curious about.
What you're listening for: Are they asking about strategy? About their career? About company stability? The questions tell you what's on their mind.
First Skip-Level Meeting Template
Duration: 30 minutes
Structure:
- 5 minutes: Rapport building (acknowledge their work, reduce status gap, restate confidentiality)
- 20 minutes: Ask 5-6 of the above questions, listen 80% of the time
- 5 minutes: Their questions for you, summarize what you heard, thank them
This template gives you valuable insights without overwhelming either party.
Questions Organized by Purpose
Once you've established trust through initial skip-levels, you can go deeper. Here are 40+ questions organized by what you're trying to accomplish.
Trust-Building Questions (Use in Early Skip-Levels)
Start here when building relationships with employees you don't know well.
- How long have you been with the company? What brought you here?
- What's the best part of your current role?
- What do you wish more people knew about the work your team does?
- Who on your team do you most enjoy working with? Why?
- What's something we're doing as a company that you're excited about?
- What would you want someone considering joining your team to know?
Team Dynamics Questions
These reveal how teams function and where relationships strengthen or strain performance.
- How would you describe your team's communication and collaboration?
- What's your team's biggest strength?
- Who on your team makes everyone around them better? How do they do it?
- If you could add one person to your team, what skills or qualities would they bring?
- What's one thing your team should start doing immediately to be more successful?
- What's one thing your team should stop doing?
- Are there any unsung heroes on your team who deserve more recognition?
- How well does your team handle disagreement or conflict?
- When something goes wrong, how does the team respond?
Process and Workflow Questions
These surface operational inefficiencies and bottlenecks.
- What's the biggest obstacle or roadblock your team faces regularly?
- Where do you see inefficiency in how work gets done?
- What information do you wish you had earlier in projects?
- What tools or resources would help your team work more effectively?
- Which meetings feel like the best use of your time? Which don't?
- What percentage of your time feels productive versus spent on low-value tasks?
- If you could eliminate one thing from your daily workflow, what would it be?
Strategic Alignment Questions
These test whether company strategy is clear and resonating at all levels.
- How well do you understand our company's current priorities?
- Do you see how your work contributes to those priorities?
- What's something we're not doing today that we should do to serve customers better?
- What trends or changes in the market should we be paying attention to?
- If you were running the company, what would you do differently?
- How do you think we compare to our competitors?
- What's the biggest risk you see for our business right now?
Manager Feedback Questions (Use Carefully)
These are sensitive. Don't lead with them in first skip-levels. Build trust first. Frame around what's working, not what's broken.
- What does your manager do particularly well?
- What's one thing your manager does that you'd like to see more of?
- Do you get enough feedback on your work?
- How comfortable do you feel sharing concerns or challenges with your manager?
- When you need support, is your manager available and responsive?
- How does your manager help you grow in your role?
- Does your manager provide clear direction on priorities?
Important: Notice none of these ask "what's wrong with your manager?" They focus on what's working and what employees need more of.
Personal Development Questions
These reveal whether employees see a future at your company.
- What are you hoping to learn or develop in your current role?
- What training or development opportunities would be valuable to you?
- How satisfied are you with your career growth here?
- What would you like to be working on that you're not currently involved in?
- Where do you see yourself in two years? What would need to happen for you to get there?
Company Culture Questions
These test whether stated values match lived experience.
- How would you describe our company culture to a friend?
- Do you feel your contributions are recognized and valued?
- What makes you feel proud to work here?
- What would make this company a better place to work?
- If you were hiring for your role, what would you emphasize about working here?
- Do you feel comfortable being yourself at work?
Crisis and Change Management Questions
Use these during periods of uncertainty or transition.
- How do you feel about [recent change or challenge]?
- What concerns do you have about the company's direction?
- How well has leadership communicated during this period?
- What information would help you feel more confident about the future?
- What support do you need that you're not getting right now?
- How has [change] impacted your day-to-day work?
Questions You Should Never Ask
Some questions undermine trust, put employees in impossible positions, or damage relationships with middle managers. Here's what to avoid and why.
1. "What's your manager doing wrong?"
Why this fails: Puts the employee in an impossible position. You're literally asking them to betray someone they work with daily. Even if they have legitimate concerns, directly criticizing their manager to you feels risky.
Instead ask: "What's one thing your manager does particularly well?" This reveals strengths naturally—and the absence of certain answers tells you plenty.
2. "Can you rate your manager on a scale of 1-10?"
Why this fails: Reduces complex relationships to numbers. Creates quantified "evidence" that feels weaponizable. Employees worry this will be used in performance reviews.
Instead ask: "When you need support, how available is your manager?" More specific, less judgment-laden, still surfaces issues.
3. "What complaints do you have?"
Why this fails: Frames the meeting as a complaint session. Trains employees to focus only on negatives. Implies you're looking for problems to punish someone over.
Instead ask: "What would make your job easier or more effective?" Forward-looking, solution-oriented, doesn't presume negativity.
4. "Are you happy working for [manager's name]?"
Why this fails: Too direct. Forces a yes/no answer with no nuance. Feels like fishing for ammunition against someone.
Instead ask: "What kind of support have you found most valuable from your manager?" Reveals what's working without demanding criticism.
5. "Who on your team isn't pulling their weight?"
Why this fails: Asking employees to do performance reviews of their peers creates a toxic environment. Nobody wants to be known as the person who reported colleagues.
Instead ask: "Who on your team picks up extra slack? Are they recognized for it?" Identifies strong contributors without forcing anyone to criticize peers.
6. "Do you think your manager is competent?"
Why this fails: Incredibly direct and threatening. Even if the answer is "no," most employees won't say it. If they do, you've compromised the relationship between them and their manager.
Instead ask: Nothing this direct. If you have serious concerns about a manager's competence, gather data through observation, their peers, and performance outcomes—not by asking their reports to judge them.
Warning from the Trenches
A management forum discussion captured this dynamic perfectly. A manager tried using skip-levels to gather 360-degree feedback on their direct reports. The expert response: "You can't use skip levels that way. It feels like you're asking people to rat out their bosses because that's exactly what you're doing."
Skip-levels should never be investigations. They're listening tours, not fact-finding missions against your middle managers.
The 80/20 Listening Rule
The questions you ask matter. But how you listen matters more.
Your Job in Skip-Level Meetings
Listen: 80% of the time Talk/Respond: 20% of the time
Most leaders get this backwards. They ask a question, hear the first sentence, then jump in to explain, defend, or solve. This shuts down the conversation and signals you're not actually interested in their perspective.
What Good Listening Looks Like
Take visible notes. Writing down what they say (or typing if virtual) shows you care enough to remember. It also slows you down and prevents interrupting.
Ask follow-up questions. Instead of jumping to solutions, dig deeper. "Can you tell me more about that?" "How long has this been an issue?" "What would ideal look like?"
Don't defend or justify. When you hear something uncomfortable—a criticism of company decisions, gaps in process, frustrations with leadership—resist the urge to explain why things are the way they are. Just listen.
Paraphrase to confirm understanding. "So what I'm hearing is [summary]. Is that accurate?" This shows you're listening and helps prevent misunderstanding.
Don't solve on the spot. Saying "I'll fix that" feels responsive but often you can't deliver immediately. Better: "That's helpful to know. Let me think about what we can do about that."
What to Avoid
Explaining why things are the way they are. Employees know you have reasons. They're telling you the impact of current reality, not asking for justification.
Defending middle managers. Even if criticism feels unfair, defending someone in the moment tells employees you're not open to feedback.
Making promises you can't keep. "I'll make sure that changes" locks you into action you may not be able to deliver.
Turning it into problem-solving. Your instinct will be to fix things. Resist. Collect information first, solve later.
Talking about your own experiences. "When I was in your role..." shifts focus back to you. Keep the spotlight on them.
Follow-Up Questions That Work
- "Can you give me an example of when that happened?"
- "What would ideal look like in that situation?"
- "How long has this been an issue?"
- "What do you think we should do about it?"
- "Who else is affected by this?"
- "What have you tried so far?"
These keep employees talking and give you richer context.
Following Up: How to Close the Loop
Skip-level meetings fail when feedback disappears into a void. If employees share concerns and nothing changes—or worse, they never hear back—they stop trusting that these meetings matter.
Here's how to close the loop effectively:
Within 24 Hours After Each Meeting
Send a brief thank-you email:
"Thanks for taking time to meet with me today. I appreciate your honesty and insights. A few things you mentioned that I'm going to think more about: [1-2 specific points]. If I have follow-up questions, I'll reach out. Thanks again."
This confirms you were listening and shows which points landed most strongly.
Within 1-2 Weeks
Look for themes across multiple skip-levels. One person mentioning communication gaps might be individual perspective. Five people mentioning it is a pattern worth addressing.
Have coaching conversations with middle managers. Without betraying confidences, share what you're seeing. "I've been doing skip-levels across the team. One theme I'm hearing is people aren't clear on how their work connects to Q1 priorities. How can we improve that communication?"
Take action on 1-2 quick wins. Find things you can fix immediately. Missing context? Write it up and share it. Inefficient process? Change it. Quick wins show people their feedback matters.
Within a Month
Share what you learned and what changed. This can be in a team meeting, company update, or email:
"Over the past month, I met with 20 people across the organization for skip-level conversations. Here's what I heard:
- Many people aren't clear on how our Q1 priorities connect to their daily work
- Team collaboration is strong, but cross-team coordination needs work
- People want more recognition for contributions
Based on that feedback, here's what we're doing:
- [Action 1]
- [Action 2]
- [Action 3]
Thanks to everyone who participated. Keep the honest feedback coming."
Why This Matters
If feedback doesn't lead to visible change, employees stop believing these meetings matter. Response rates drop. Candor disappears. The whole exercise becomes performative.
But when people see their input leading to real changes—even small ones—they engage more deeply next time.
Making Skip-Levels Sustainable
One-off skip-levels are better than nothing. But regular skip-levels build lasting trust and keep you connected to what's actually happening.
The challenge: Manually scheduling dozens of one-on-ones with people several layers down is time-consuming and often gets deprioritized when things get busy.
Here's how to make skip-levels sustainable:
1. Block Calendar Time Quarterly
Dedicate 1-2 days per quarter specifically for skip-level meetings. Put it on your calendar at the start of the year. Protect this time like you would board meetings or customer commitments.
2. Rotate Teams if Necessary
If you can't meet with everyone quarterly, rotate which teams you engage with. Over 6-12 months, everyone gets a turn. This maintains connection without overwhelming your calendar.
3. Use Automation Thoughtfully
Tools like Bettermeets can help schedule skip-levels systematically without making them feel bureaucratic:
Automatically rotate through teams on a set cadence so no one falls through the cracks.
Send prep emails to employees with context about the meeting's purpose and a few example questions. This reduces anxiety and improves conversation quality.
Track who you've met with and when so you can maintain consistency across the organization.
Capture themes across meetings over time so patterns become visible rather than lost in individual notes.
The key: Automation handles logistics—scheduling, reminders, tracking—so you can focus energy on listening rather than coordinating calendars.
4. Make It Optional But Expected
Don't mandate skip-level attendance. "You have to meet with me" creates a "you're in trouble" dynamic.
Instead, communicate that skip-levels are a regular part of how you stay connected. Most employees will opt in when they understand the purpose and see that feedback leads to action.
5. Keep Meetings Short
Thirty minutes is plenty. Longer meetings increase scheduling difficulty and create fatigue. You're not trying to solve all problems in one conversation—you're building connection and understanding over multiple touchpoints.
Conclusion
Skip-level meetings are powerful when you ask the right questions in the right way. They give you unfiltered access to what's happening on the front lines, build trust across organizational layers, and help you coach your middle managers more effectively.
But they can also backfire spectacularly if you use them as investigations of your direct reports or put employees in positions where they feel forced to criticize people they work with daily.
The principles are straightforward:
Start with trust-building questions, not diagnostic interrogations. Build rapport before seeking insights.
Never ask employees to directly critique their managers. Frame questions around what's working and what they need more of.
Listen 80% of the time. Resist the urge to explain, defend, or solve in the moment.
Follow up visibly. Show that feedback leads to action, even if the actions are small.
Make skip-levels regular, not one-off. Consistency builds trust more than any single perfect meeting ever will.
When you get this right, skip-levels stop feeling like audits and start feeling like genuine conversations. Information flows more freely. Issues surface before they become crises. And employees feel like leadership actually cares what's happening in their world.
That's worth the investment.
Ready to make skip-level meetings consistent? Bettermeets integrates with your calendar to systematically schedule skip-levels, send prep materials, and track themes over time. Stop letting skip-levels slip through the cracks when things get busy. Try Bettermeets free →
Resources
Related Articles:
- Benefits of Feedback Meetings - Build a culture of continuous feedback
- Meeting Feedback Questions - Improve your meeting effectiveness
- Optimal Meeting Length - Right-size your meetings
External Resources:
- Harvard Business Review: The Feedback Fallacy - Rethinking how we give feedback
- Gallup: Employee Recognition Impact - Research on recognition and performance