Skip-level meeting questions are the questions a senior leader asks employees who report to one of their managers, or that those employees ask the senior leader, in a skip-level meeting. Good questions build trust, show how the team really works and end with clear next steps. Below are 165 questions in two sets: questions 1–98 for leaders to ask employees, and questions 99–165 for employees to ask their skip-level manager.
New to skip-levels? Our guide explains what a skip-level meeting is and how to run one. If you are the employee, see how to prepare for a skip-level meeting.
Key takeaways
- Pick 5 to 7 questions per meeting; never try to ask them all.
- Start with rapport, spend most of the time on one topic, and always close by agreeing on a follow-up.
- Brief the direct manager first and promise confidentiality, or you will only hear safe answers.
- Look for themes across several meetings, not single comments, and tell people what you changed.
The 10 best skip-level meeting questions
Short on time? These ten cover rapport, the manager, the team, obstacles, growth and follow-up. The numbers refer to the full list below.
- What was the highlight of your week so far? (#1)
- What is one thing your manager does exceptionally well? (#16)
- What is one thing your manager could improve on? (#17)
- On a scale of 1–10, how would you rate team morale? Why? (#36)
- What is the biggest bottleneck in your daily work? (#56)
- What information do you not have access to that you need? (#68)
- Do you see a path to achieve your career goals here? (#80)
- On a scale of 1–10, how excited are you about your future at this company? (#95)
- Of everything we discussed, what was the most important topic for you? (#96)
- What is one specific thing you will hold me accountable to follow up on? (#97)
Why skip-level meetings matter
Skip-level meetings are not about micromanagement. Done well, they help leaders and employees in five ways:
- Build trust and transparency: they show employees that leadership is accessible and values their view.
- Develop your managers: they give you anonymised feedback to coach your direct reports. Gallup estimates that managers account for at least 70% of the variance in team engagement, so manager quality matters.
- Uncover ground truth: they reveal process bottlenecks and team dynamics that rarely show up in reports.
- Support retention: employees who feel heard are more likely to raise problems early instead of quietly leaving.
- Align strategy: they check that company goals are understood and turned into the right work.
Four rules for a psychologically safe meeting
Before you ask a single question, create an environment of trust and psychological safety. Without it, you will only get surface-level answers.
- Brief direct managers first: tell your direct reports that these meetings support their development and the health of the team, not an inspection. Get their buy-in beforehand.
- Promise confidentiality: open with a clear statement, for example: "This is a confidential conversation. Nothing you say will be shared with your manager or anyone else in a way that identifies you, without your permission."
- Listen to understand, not to respond: resist the urge to justify, explain or solve problems in the moment.
- Commit to action: take visible notes, look for themes and follow up. Feedback without visible action erodes trust faster than no meeting at all.
How to use this question bank (sample agenda)
This is a menu, not a checklist. For a 45–60 minute meeting, pick 5 to 7 questions in total:
- 5–10 minutes, rapport: 2 questions from "Building rapport".
- 20–30 minutes, main topic: 3–4 questions from one other section.
- 5–10 minutes, second topic: 1–2 questions from a different section.
- 5 minutes, closing: always ask the three closing questions (#96–98).
Skip-level meeting questions for leaders to ask employees (1–98)
Use these when you are the senior leader meeting employees who report to one of your managers.
Building rapport
- What was the highlight of your week so far?
- What’s a hobby or interest you’re passionate about outside of work?
- What’s the best book you’ve read recently?
- What’s a podcast you’re currently hooked on?
- What show are you binge-watching right now?
- What is your idea of a perfect weekend?
- What is the most memorable trip you’ve ever taken?
- If you could travel anywhere tomorrow, where would you go?
- What’s the best meal you’ve ever had?
- Who is your favorite musician or band of all time?
- What was the first concert you ever attended?
- What’s a fun or interesting fact about you that not many people know?
- What are you most proud of in the last year, personally?
- How do you like to recharge after a long day?
- If you could have a superpower, what would it be and why?
Your manager’s leadership and communication
- What is one thing your manager does exceptionally well?
- What is one thing your manager could improve on?
- How would you describe your manager’s leadership style?
- How effective is your manager at communicating goals and expectations?
- Does your manager provide clear and actionable feedback?
- How does your manager handle it when you make a mistake?
- How does your manager act during high-pressure or crisis situations?
- Does your manager empower you to make decisions?
- Do you feel micromanaged or trusted in your role?
- How does your manager recognize and celebrate your wins?
Your manager’s support and development
- How does your manager support you when you’re struggling?
- Is your manager approachable and available when you need them?
- How does your manager support your career development?
- Does your manager help you get access to resources and training?
- Do your 1:1 meetings with your manager feel valuable? Why or why not?
- What percentage of your manager's feedback is positive vs. constructive?
- Does your manager publicly credit team members for their work?
- How does your manager handle underperformance on the team?
- Does your manager advocate for the team to upper management?
- On a scale of 1–10, how would you rate your manager’s effectiveness? Why?
Team culture and psychological safety
- On a scale of 1–10, how would you rate team morale? Why?
- How would you describe the team’s culture in three words?
- How effectively does the team collaborate?
- Is there a sense of trust and safety within the team?
- How does the team handle disagreements or conflict?
- Are team meetings productive and engaging?
- How are decisions made within the team?
- Does everyone on the team pull their weight?
- Without naming names, is there a perception of unfairness in workload?
- Who on the team is an unsung hero?
Team processes and collaboration
- How inclusive is the team environment?
- Do team members socialize outside of work?
- How does the team onboard and support new members?
- What is the team’s biggest strength?
- What is the team’s biggest weakness?
- What is one thing the team should start doing?
- What is one thing the team should stop doing?
- What is one thing the team should continue doing?
- How does the team celebrate successes?
- How does the team handle failures?
Daily workflow and tools
- What is the biggest bottleneck in your daily work?
- What process is overly complicated or bureaucratic?
- What tool or software is missing from our stack?
- What existing tool or software is ineffective?
- What meeting could be eliminated or improved?
- How much time do you spend on "work about work" (reporting, updating trackers)?
- How easy is it to get a decision made?
- How easy is it to get a budget approved?
- How easy is it to get a resource you need?
- What always seems to fall through the cracks?
Strategy, communication and resources
- If you were CEO for a day, what's the first operational change you'd make?
- How effective is our internal communication?
- What information do you not have access to that you need?
- How clear are our goals and priorities from a company level?
- How does strategy get translated into actionable work for your team?
- What is the biggest gap between strategy and execution?
- What is the biggest risk to our projects that nobody is talking about?
- How effective is our project management?
- How effective is our knowledge management (e.g., wikis, documentation)?
- Is it easy to find information you need?
Role, strengths and career goals
- What do you enjoy most about your current role?
- What do you enjoy least about your current role?
- What are your short-term career goals (1–2 years)?
- What are your long-term career goals (3–5+ years)?
- Do you see a path to achieve those goals here?
- What skills would you like to develop right now?
- What skills are you not using that you’d like to use?
- What type of work energizes you?
- What type of work drains you?
- What part of your job would you like to do more of?
Growth and retention
- What part of your job would you like to do less of?
- What kind of training would be most beneficial for you?
- What conference would you love to attend?
- Who in the company would you like to learn from?
- Are you interested in finding a mentor?
- Are you interested in being a mentor?
- What does your ideal next role look like?
- Do you feel you are paid fairly for your role and experience?
- How do you feel about your benefits package?
- On a scale of 1–10, how excited are you about your future at this company?
Closing questions (always ask these)
- Of everything we discussed, what was the most important topic for you?
- What is one specific thing you will hold me accountable to follow up on?
- Is there anything we didn’t talk about that you thought we would?
Skip-level meeting questions for employees to ask (99–165)
Use these when you are the employee meeting your manager’s manager. Pick three to five that match what you want from the meeting, such as career advice or a clearer view of strategy.
Getting to know the leader
- What do you enjoy most about your role?
- What’s the biggest challenge in your role?
- What does a typical day look like for you?
- How did you get to where you are in your career?
- What was your first role at this company?
- What’s the best career advice you’ve ever received?
- Who has been a mentor to you?
- What’s a book that has significantly influenced your leadership style?
- What’s a failure you experienced, and what did you learn from it?
- What are you most proud of in your career?
Performance and impact
- From your perspective, what are the most valuable skills in my role?
- What skills will be most important for the future of my department?
- How do you define success for someone in my position?
- What are the key performance indicators (KPIs) you care most about for our team?
- What does "exceeding expectations" look like for my role?
- What opportunities do you see for me to have a greater impact?
- Are there any projects you’re aware of that could use my skillset?
- What is a problem you’re trying to solve that I could help with?
- How can I better align my work with the company’s top priorities?
Career paths and promotion
- What is one thing I could do differently to be more effective?
- What is one thing I should keep doing because it’s highly valuable?
- How can I improve my visibility and influence within the company?
- Who would you recommend I connect with to learn more about [X]?
- What training or certifications would you recommend for me?
- How can I prepare myself for a potential future leadership role?
- What are the biggest challenges someone at my level faces when trying to advance?
- What are you looking for when you consider someone for promotion?
- How does the promotion process truly work?
- What is the most common reason why people don’t get promoted here?
Company strategy and future
- In your own words, what is the company’s most important goal this year?
- What is the company’s biggest competitive advantage right now?
- What is the company’s biggest weakness or threat?
- What are you most excited about for the company’s future?
- What keeps you up at night regarding the company?
- How does the strategy you’re working on translate down to my team’s goals?
- How can employees at my level contribute to the company’s long-term vision?
- What does the company’s five-year vision look like?
- How do you see our industry changing in the next five years?
- How is the company preparing for those changes?
Culture and values
- What does our company value most: innovation, efficiency, customer focus or something else?
- How are the company’s values actually used in decision-making?
- Can you give an example of a tough decision where values played a key role?
- How is the company working to improve diversity, equity and inclusion?
- What is the company’s philosophy on remote and hybrid work?
- How does the company think about its social responsibility?
- What is the biggest cultural challenge the company faces?
- What is one thing you would change about the company’s culture if you could?
- How does the company encourage innovation and new ideas?
- What happens when someone fails at a new idea here?
- How does the company make sure it’s listening to employees?
- What was the best piece of feedback from employees that led to a real change?
Department priorities and challenges
- What is the biggest priority for our department right now?
- What is the biggest challenge our department is facing?
- How does our department’s work impact the company’s bottom line?
- How could our department collaborate more effectively with [X department]?
- What is another department doing really well that we could learn from?
- What are the biggest inefficiencies you see in our department?
- What technology or tools are we missing that could help us?
- Are there any new roles or teams being planned for our department?
- How is our department performing against its goals?
- What is a new skill our department needs to build?
- How do you see our department evolving in the next two years?
- What is the biggest opportunity our department is not yet pursuing?
- What is the biggest misconception other departments have about us?
- How can I help improve collaboration between my team and others?
- What is one thing I can do to help our department be more successful?
- Is there anything else about the department’s direction I should know?
After the meeting: from conversation to action
The real work begins after the meeting. Your follow-through is what builds lasting trust.
- Find themes: review your notes across all meetings and look for patterns, not isolated complaints.
- Coach, don't punish: use manager-related feedback to coach your direct reports. Frame it as development data: "I've heard from a few team members that..."
- Fix systemic issues: take process and strategy themes to other leaders and remove roadblocks for everyone.
- Close the loop: send employees a short summary of the themes you heard and the actions you are taking. Short pulse surveys between meetings show whether things are improving.
Skip-Level Meeting Questions: FAQ
As a leader, ask one or two rapport questions, three or four about one topic such as the manager, the team or daily obstacles, and always close by asking what matters most to the employee and what you should follow up on. As an employee, ask about how success is judged in your role, where the company is heading and what it takes to grow.
Five to seven questions are enough for a 45 to 60 minute meeting. Fewer, deeper questions with follow-ups get more honest answers than a long list read out in order.
Employees should avoid personal attacks on their manager or colleagues; describe specific situations and their impact instead. Leaders should avoid defending decisions on the spot, promising changes they cannot make, or asking employees to name individuals.
They should be. Leaders should say at the start that comments will not be shared with the employee’s manager in a way that identifies them, and only share themes from several meetings. Serious issues such as harassment may still need to go to HR.
Many leaders meet each employee once or twice a year, or hold quarterly small-group sessions for larger teams. Consistency matters more than frequency: a predictable rhythm makes the meetings feel normal rather than a sign that something is wrong.
Ask with curiosity, act on what you hear
The right skip-level questions turn a distant leader into a connected one. Ask with genuine curiosity, listen without defending, and show people what changed because they spoke up. Use these questions not as an interrogation, but as an invitation to a more honest conversation.
To keep hearing from your teams between meetings, Newployee's employee survey software lets you run short pulse surveys in a few clicks.
