Skip Level Meeting Questions: 40+ Examples

Skip level meeting questions are the backbone of productive conversations between senior leaders and employees who don't report to them directly. When done right, these meetings surface insights that never make it through the usual chain of command — the kind of honest feedback that helps small teams stay aligned, fix problems early, and grow faster.

This guide gives you 40+ ready-to-use questions organized by category, plus a practical framework for running skip level meetings that actually work.

What Is a Skip Level Meeting?

A skip level meeting is a one-on-one conversation between an employee and their manager's manager — "skipping" one level of hierarchy. The direct manager isn't present.

Think of it this way: if your org chart has three levels — CEO, team lead, and individual contributor — a skip level meeting happens when the CEO sits down with the individual contributor directly.

Unlike a regular one-on-one meeting, skip levels aren't about project updates or task management. They're about understanding what's really happening on the ground — team morale, leadership effectiveness, and whether the company's direction makes sense to the people doing the work.

Why Skip Level Meetings Matter for Small Teams

At a 200-person company, skip levels are a nice-to-have communication tool. At a 15-person startup, they can be transformative.

Here's why. Small teams already have short communication lines, but that doesn't mean information flows freely. A 2024 study published in the Harvard Business Review found that employees who have regular skip level conversations with senior leaders report 23% higher engagement scores than those who don't. When your entire company fits in one room, that engagement boost matters even more.

Three reasons skip levels hit different at small companies:

1. Every voice carries weight. With 10–50 employees, one disengaged person drags the whole team. Skip levels catch frustration before it becomes turnover.
2. Founders wear multiple hats. You're the CEO, the HR department, and sometimes the IT help desk. Skip levels give you a structured way to check on people without adding another meeting to everyone's calendar — because it replaces informal hallway conversations that stop happening as you grow.
3. Managers are often new to management. Your first team lead probably got promoted because they were great at their job, not because they had management training. Skip levels give you a window into how they're doing as a leader, straight from the people they lead.

How to Set Up Skip Level Meetings

Getting the logistics right prevents awkward conversations and wasted time. Here's a step-by-step approach:

Step 1: Talk to your managers first. Announce the program openly. Explain that skip levels aren't about checking up on anyone — they're about improving communication. A manager who feels blindsided will be defensive, and that defensiveness will trickle down to their reports.

Step 2: Set a cadence. For teams under 20 people, monthly works well. For teams of 20–50, rotate quarterly so you meet each person at least twice a year. Block 30 minutes per session — enough for a real conversation, short enough to stay focused.

Step 3: Establish ground rules. Share these with everyone:

• Conversations are confidential unless there's a safety or legal concern
• This is not a performance review or a reporting session
• Both parties should come with at least one topic to discuss
• Feedback about managers will be used for coaching, not punishment

Step 4: Send a pre-meeting prompt. Two days before the meeting, send something like: "Looking forward to our skip level. Feel free to bring anything you'd like to discuss — team dynamics, your career, ideas for the company, or questions for me."

According to SHRM's guide on skip level meetings, the most common mistake leaders make is treating these as interrogation sessions rather than two-way conversations. Keep it relaxed.

Skip Level Meeting Questions About Team Dynamics

These questions help you understand how the team actually functions day to day — not how it looks on paper.

1. How would you describe your team's energy right now? High, steady, or drained?
2. When your team disagrees on something, how does it usually get resolved?
3. Is there anyone on your team who consistently goes above and beyond but doesn't get recognized for it?
4. What's one thing your team does really well that other teams could learn from?
5. If you could change one thing about how your team works together, what would it be?
6. Do you feel like your team has the right number of people, or are you stretched thin?
7. How well does your team handle unexpected problems or shifting priorities?
8. Is there a recurring frustration on your team that nobody talks about?
9. What's the best collaboration your team has had recently? What made it work?
10. If a new person joined your team tomorrow, what would surprise them most about how things work?

Tip: Question 8 is the one that surfaces the gold. People will pause before answering — give them space. The silence is where honesty lives.

Questions About Career Growth and Development

Career development is one of the top reasons people leave small companies. These skip level meeting questions help you understand whether your team feels like they're growing or stagnating.

1. Where do you see yourself in this company a year from now?
2. What skills are you most eager to develop right now?
3. Do you feel like there's a clear path for advancement here? What's unclear about it?
4. Is there a project or responsibility you'd love to take on but haven't had the chance?
5. When was the last time you learned something new at work? What was it?
6. Do you feel like your current role uses your strengths, or are some of your talents going unused?
7. What kind of mentorship or support would make the biggest difference for your growth?
8. Have you considered other roles within the company? What interests you?
9. Is there anything holding you back from performing at your best?
10. What would make this the best job you've ever had?

A study from Gallup's State of the Global Workplace report found that lack of development opportunities is the number one reason employees leave their jobs. For small teams, losing even one key person can set you back months. Use these questions to spot flight risks early.

Pair these conversations with a structured performance review process to turn insights into action.

Questions About Management and Leadership

This is the most sensitive category. You're asking someone to give honest feedback about their boss — to their boss's boss. Framing matters enormously.

Never ask "Is your manager good?" Instead, ask about specific behaviors and situations:

1. What's something your manager does that really helps you do your best work?
2. How does your manager handle it when you make a mistake?
3. Do you feel comfortable bringing problems or concerns to your manager? Why or why not?
4. How does your manager give you feedback? Is it helpful?
5. Does your manager clearly communicate priorities, or do you sometimes feel unsure about what matters most?
6. What's one thing your manager could do differently to support the team better?
7. How does your manager handle conflict between team members?
8. Do you feel your manager advocates for your team with the rest of the company?
9. When's the last time your manager gave you recognition? How did they do it?
10. If you could give your manager one piece of anonymous advice, what would it be?

Important: Never use skip level feedback to confront a manager directly. The goal is patterns, not incidents. If three people independently mention that priorities are unclear, that's coaching gold. But you deliver it as a general observation, not "Sarah told me you don't communicate well."

This feedback pairs well with 360 feedback questions and constructive feedback examples to create a complete picture of management effectiveness.

Questions About Company Culture and Communication

Culture isn't what you write on the wall — it's what people experience every day. These questions reveal the gap between your intended culture and the reality.

1. How would you describe our company culture to a friend considering joining?
2. Do you feel like you know where the company is headed? What's clear or unclear?
3. Is there any information you wish leadership shared more openly?
4. Do you feel like your ideas and opinions are genuinely considered here?
5. What's one thing about our culture that you'd hate to see change?
6. Is there anything about how we communicate as a company that frustrates you?
7. Do you feel like different teams collaborate well, or does it feel siloed?
8. How do you feel about the pace of change here — too fast, too slow, or just right?
9. If we hired 10 new people next month, what's one cultural value you'd want them to understand immediately?
10. What's one company-wide change that would make your work life significantly better?

Questions to Ask as an Employee (Reverse Skip Level)

Skip levels aren't just a leadership tool. If you're the employee in the room, you have a rare opportunity to get perspective from someone with a wider view of the company.

Here are questions that make you stand out as thoughtful and engaged:

• What's the biggest challenge the company is facing right now that I might not be aware of?
• What qualities do you look for when promoting people internally?
• Is there anything my team could be doing differently to better support the company's goals?
• What's one thing you wish more employees understood about running this company?
• How can I be more visible in my contributions without overstepping?
• What's one skill you think will become more important here over the next year?

The key to being a great skip level participant is asking questions that show you care about the company's success, not just your own. Senior leaders remember employees who think beyond their individual role.

Tips for Effective Skip Level Meetings

After running hundreds of skip levels (and watching leaders botch plenty of them), here's what separates productive conversations from polite wastes of time:

1. Don't take notes during the meeting. Jot down key themes afterward. A notebook on the table signals "this is being recorded" and kills candor. If you need to remember something specific, ask permission: "Mind if I write that down?"

2. Follow up on what you heard. Nothing destroys trust faster than asking for feedback and then doing nothing with it. Even a simple message — "I heard from several people that X is a pain point, and here's what we're doing about it" — shows people their time mattered.

3. Start with something personal. Ask about their weekend, their hobbies, their family. Two minutes of genuine human connection makes the next 28 minutes more honest. This isn't small talk — it's rapport building.

4. Rotate your questions. Don't ask the same 10 questions every time. Pick 3–5 per session from different categories. This keeps conversations fresh and gives you a broader dataset over time.

5. Watch for patterns across meetings. Individual feedback is anecdotal. But when multiple people independently surface the same theme, you've found something real. Track themes in your people management system to spot trends over time.

Frequently Asked Questions

How often should you have skip level meetings?

For teams under 20 people, monthly skip levels work well — it's frequent enough to catch issues early without overwhelming anyone's calendar. For companies with 20–50 employees, quarterly rotations ensure every person gets face time with senior leadership at least twice a year. The key is consistency: sporadic skip levels feel like something's wrong, while regular ones feel like part of the culture.

What's the difference between a skip level meeting and a one-on-one?

A one-on-one is between an employee and their direct manager, focused on day-to-day work, tasks, and immediate goals. A skip level meeting is between an employee and their manager's manager, focused on bigger-picture topics like culture, leadership feedback, and career growth. Both are valuable — they serve different purposes. Check out our one-on-one meeting template for structuring regular 1:1s.

Should managers know what's discussed in skip level meetings?

Not the specifics. The whole point of skip levels is creating a safe space for honest feedback. However, managers should know that skip levels are happening — no one likes being blindsided. Share aggregated themes with managers during coaching conversations, but never attribute specific comments to individuals.

How do you handle negative feedback about a manager in a skip level?

Listen without reacting. Thank the employee for their honesty. Then look for patterns across multiple skip levels before acting. If only one person mentions an issue, it might be a personality clash. If three people independently raise the same concern, it's a coaching opportunity. Use structured performance reviews to address management development.

Can skip level meetings work in remote teams?

Absolutely — and they might be even more important. Remote employees often feel less connected to leadership and company direction. Video calls work well for skip levels, though some leaders prefer walking meetings or casual virtual coffee chats. The format matters less than the consistency and the quality of questions you ask.

What should an employee do to prepare for a skip level meeting?

Come with two or three topics you genuinely want to discuss. Think about what's going well, what could be better, and what questions you have about the company's direction. Don't treat it as a venting session or a performance review — treat it as a real conversation with someone who has a different perspective than your direct manager.