Interview guide · Employee lifecycle interviews
Skip level meeting questions
In short
Skip level meeting questions help a senior leader hear directly from employees who report to their managers: what gets in the way of the work, how the team runs, what people want next and what leadership is missing. Below are 31 questions in six groups, including questions employees can ask, plus how to run skip levels and act on them.
A skip level meeting is a conversation between a leader and employees one level or more below their direct reports, without the middle manager in the room. A director meets with agents on a team lead's team; an operations VP meets with site supervisors. The goal is to hear what does not travel up the chain: friction that has become normal, ideas that never got past the first manager and early signs of trouble on a team.
The meeting works only if employees believe two things: that speaking candidly will not hurt them, and that something will happen as a result. Pick five to seven questions for a 30 minute one-on-one, or three or four for a small group. Start with the work, not the manager. Questions about the employee's manager are useful, but asked first they make the meeting feel like an investigation. If you already run stay interviews, compare themes: skip levels catch team-wide issues that individual stay conversations can miss.
What these questions assess
- Recurring obstaclesWhen three people on different teams name the same broken tool or policy, it is an organizational problem only a senior leader can fix.
- Signals about the middle managerPatterns matter more than single comments. Consistent mentions of unclear priorities, favoritism or no one-on-ones point to a coaching need for the manager.
- Hidden talentSkip levels are one of the few ways senior leaders meet strong individual contributors directly. Note people who think beyond their own role.
- Understanding of directionIf employees cannot explain what the organization is trying to do this year, communication is breaking down somewhere between you and them.
- Trust and candorShort, careful answers across a whole team suggest low psychological safety, which is a finding in itself.
Openers and rapport
What does a typical week look like for you right now?
- Why ask it
- Easy opener that gives the leader a ground-level picture of the role.
- A strong answer
- Concrete detail about tasks, volume, meetings and where time goes.
- Red flags
- A week dominated by workarounds, rework or waiting on other teams.
What part of your job do you enjoy most at the moment?
- Why ask it
- Starts positively and shows where energy comes from.
- A strong answer
- A specific task, customer type or project, ideally with why.
- Red flags
- Struggles to name anything, which can signal disengagement.
What has changed most in your work over the last six months?
- Why ask it
- Shows how recent decisions landed at the front line.
- A strong answer
- Specific changes and their real effect, positive or negative.
- Red flags
- Changes they learned about late or without explanation.
What do you wish senior leaders understood about your job?
- Why ask it
- Directly invites the information skip levels exist to collect.
- A strong answer
- A specific reality, such as how long a system takes to load or what customers actually ask about.
- Red flags
- Resignation, such as 'they would not care anyway'.
Is there anything you were hoping to talk about today?
- Why ask it
- Gives the employee control of the agenda early.
- A strong answer
- A prepared topic, which shows they take the meeting seriously.
- Red flags
- None; many people have nothing prepared the first time.
The work and what gets in the way
What is the most frustrating part of getting your work done?
- Why ask it
- The core skip level question. Front-line frustration is often invisible higher up.
- A strong answer
- A specific, fixable obstacle with an example.
- Red flags
- The same obstacle you heard from the last three people, which needs action now.
If you could remove one step, tool or approval from your job, what would it be?
- Why ask it
- Turns complaints into concrete process improvement.
- A strong answer
- A step with a clear explanation of why it adds no value.
- Red flags
- None; record suggestions and report back on them.
Where do you see us wasting time or money?
- Why ask it
- Employees often see waste leaders cannot.
- A strong answer
- Examples such as duplicate data entry, unused licenses or meetings without decisions.
- Red flags
- None.
What do customers complain about that we are not fixing?
- Why ask it
- Brings the customer voice into the conversation from the people who hear it daily.
- A strong answer
- Specific recurring complaints, with volume or examples.
- Red flags
- Complaints that have been raised before and ignored.
Do you have the information you need to make decisions in your job without waiting for someone?
- Why ask it
- Tests empowerment and access to data.
- A strong answer
- Yes, or a specific gap such as approval limits that are too low.
- Red flags
- Frequent waiting for approvals on routine decisions.
Which other team do you depend on most, and how is that working?
- Why ask it
- Surfaces cross-team friction that rarely reaches leadership.
- A strong answer
- Honest description of handoffs, delays and what would help.
- Red flags
- Blame without specifics, or a handoff that routinely fails.
Team and manager
How would you describe how your team works together?
- Why ask it
- Opens a team conversation without targeting the manager.
- A strong answer
- Specific examples of collaboration, covering for each other, or friction.
- Red flags
- Cliques, conflict nobody addresses or people working in isolation.
How often do you get one-on-one time with your manager, and is it useful?
- Why ask it
- A neutral factual question that reveals a lot about management habits.
- A strong answer
- Regular meetings with real content, such as feedback and planning.
- Red flags
- Meetings canceled often or used only for status updates.
What does your manager do that helps you most?
- Why ask it
- Gives balanced information and something to recognize.
- A strong answer
- Specific behaviors, such as shielding the team from noise or explaining decisions.
- Red flags
- Nothing they can name.
What could your manager do differently that would help you?
- Why ask it
- Invites constructive feedback in a forward-looking way.
- A strong answer
- Specific, fair suggestions.
- Red flags
- Fear of answering, or serious concerns such as harassment, which must go through proper channels.
Do you feel comfortable raising problems on your team? Why or why not?
- Why ask it
- Directly tests psychological safety.
- A strong answer
- Yes, with an example of a problem raised and handled.
- Red flags
- No, or a story of someone who raised an issue and suffered for it.
Growth and career
Where do you want your career to go in the next two or three years?
- Why ask it
- Shows ambition and whether the organization has a path for it.
- A strong answer
- A clear goal you can connect to real roles or projects.
- Red flags
- A goal they believe is impossible here.
Do you know what it would take to get to the next level?
- Why ask it
- Tests whether promotion criteria are understood.
- A strong answer
- A clear understanding of expectations and their current gaps.
- Red flags
- No idea, which points to a manager or process gap.
What have you learned in the last six months?
- Why ask it
- Shows whether development is happening in practice.
- A strong answer
- Specific skills, projects or training.
- Red flags
- Nothing new, especially for high performers.
Is there a project or team you would like to be involved with?
- Why ask it
- Identifies stretch opportunities a senior leader can open.
- A strong answer
- A specific interest connected to their skills.
- Red flags
- None.
Have you thought about leaving in the last year? What made you stay?
- Why ask it
- A retention check that also shows what anchors people.
- A strong answer
- Honest answer with a specific reason for staying.
- Red flags
- An active job search or a single fragile reason to stay.
Direction and communication
In your own words, what is our team or department trying to achieve this year?
- Why ask it
- Tests whether strategy reaches the front line.
- A strong answer
- A reasonable summary that matches what leadership intends.
- Red flags
- A confused or very different answer, which means the message is not landing.
How do you usually find out about important changes?
- Why ask it
- Maps actual communication channels.
- A strong answer
- Through their manager or official channels, in time to prepare.
- Red flags
- Rumors, chat threads or the day the change happens.
Which recent decision did you not understand the reason for?
- Why ask it
- Shows where leaders need to explain more.
- A strong answer
- A specific decision you can explain now or follow up on.
- Red flags
- Several decisions seen as arbitrary.
If you were in my role for a month, what would you change first?
- Why ask it
- Invites big-picture ideas from people closest to the work.
- A strong answer
- A concrete, reasoned change.
- Red flags
- None.
What should I keep doing, start doing or stop doing as a leader?
- Why ask it
- Gives the senior leader direct feedback on their own impact.
- A strong answer
- Honest, specific feedback.
- Red flags
- Only praise, which may reflect low trust.
Questions employees can ask in a skip level meeting
What are the top priorities for our department this year, and how does my team's work connect to them?
- Why ask it
- Shows the employee cares about context and impact.
- A strong answer
- From the leader: a clear answer linked to the team's daily work.
- Red flags
- A vague answer suggests priorities are unclear at the top too.
What do you see as the biggest challenge for our area in the next six months?
- Why ask it
- Gives the employee insight into what is coming.
- A strong answer
- An honest answer the employee can prepare for.
- Red flags
- None.
What skills do you think will matter most for people in my role going forward?
- Why ask it
- Helps the employee plan development.
- A strong answer
- Specific skills the leader expects to need.
- Red flags
- None.
How do you like to hear about problems or ideas from people outside your direct team?
- Why ask it
- Opens a channel without going around the direct manager.
- A strong answer
- A clear, respectful process that keeps the manager informed.
- Red flags
- None.
What does great performance look like from where you sit?
- Why ask it
- Shows how senior leadership judges results.
- A strong answer
- Concrete examples of what gets noticed.
- Red flags
- None.
Sample answers
Honestly, it is the refund approvals. Anything over $75 has to go to a supervisor, and on evenings there are two supervisors for about forty of us. So I tell the customer I will call them back, I put it in the queue, and sometimes it sits until the next day. Then they call again, they get someone else, and that person has to read through everything. I would guess I do six or seven of those a shift. Most of them are completely routine, like a double charge. If agents who have been here a year could approve up to $150, I think half those callbacks would go away. Kevin knows about it; I think he has raised it, but nothing has changed yet.
With Kevin, yes. He is pretty open, and when I told him the new schedule was hard with my class nights he moved me within a week. With the team in general it is a little harder. A couple of months ago someone mentioned in a team huddle that the quality forms were scored inconsistently, and the QA lead took it personally. Since then people mostly keep quiet in group meetings and just complain in the break room. I do not think anyone means harm, but if there were a way to give feedback on QA scoring without it being so public, I think you would hear a lot more.
Interview scorecard
| Competency | Weight | Strong (4–5) | Weak (1–2) |
|---|---|---|---|
| Operational friction | 25% | Few obstacles; those named are minor or already being fixed. | A recurring obstacle that costs hours weekly or affects customers, raised repeatedly without action. |
| Manager effectiveness signals | 25% | Regular useful one-on-ones, clear priorities, fair treatment described with examples. | No regular contact, unclear priorities or consistent concerns from several people. |
| Psychological safety | 20% | Candid answers, examples of problems raised and handled. | Guarded answers, fear of consequences or stories of retaliation. |
| Growth and retention outlook | 15% | Clear goal and understanding of the path to it. | No visible path, active job search or high performer with no development. |
| Alignment with direction | 15% | Can explain priorities and why recent decisions were made. | Confused about goals and learns about changes through rumors. |
Score each competency from 1 to 5 straight after the interview, before discussing the candidate with anyone else, then multiply by the weight.
How to run a skip level meeting
Tell the middle managers first. Explain that skip levels are routine, that you will share themes rather than attributions, and that you are not checking up on them. Managers who feel ambushed will undermine the process.
Choose the format. One-on-ones of 20 to 30 minutes work for teams of up to about 30 people under a leader. For larger groups, such as an operations director over 200 agents, hold small group sessions of five to eight people, rotating through teams quarterly. Our one-on-one meeting template works for notes in either format.
Set expectations at the start. Say what happens with what they share: themes go back to managers, individual comments stay confidential unless they involve safety, harassment or legal issues that must be reported. Do not promise confidentiality you cannot keep.
Close the loop. Within two weeks, share back what you heard and what will change, even if the answer on some issues is no and why. Skip levels that produce no visible action lose credibility after one round.
Mistakes that damage trust
The fastest way to ruin skip levels is to repeat an individual's comment to their manager with their name on it. The second is acting on a single complaint about a manager as if it were proven. Look for patterns across people and check them through normal channels before drawing conclusions; when a serious allegation comes up, refer it to HR or employee relations rather than investigating it yourself.
Leaders also talk too much. If you spend 20 of 30 minutes explaining strategy, you have held a town hall, not a skip level. Aim for the employee talking 70% of the time. Finally, do not hold skip levels only when there is trouble on a team; that makes them feel like an investigation. Run them on a regular rhythm across all teams.
Skip levels in large frontline operations
In a contact center or distribution network, span of control makes one-on-one skip levels with everyone impossible. A site director over 400 people can still cover a lot of ground with two 45 minute group sessions a week, mixing agents from different teams so no one team lead feels singled out. Cover every shift, including nights and weekends, where problems are often worst and leaders rarely visit.
Between sessions, a short anonymous pulse survey can track the themes raised. HR business partners often help run the program, combine notes and spot cross-site patterns; the skills involved are similar to those covered in our HR business partner interview questions. When skip level themes match what people said in exit interviews, treat them as the top priorities.
Frequently asked questions
What is a skip level meeting?
A meeting between a senior leader and employees who report to that leader's direct reports, without the middle manager present, to hear directly about the work, the team and ideas for improvement.
What questions should I ask in a skip level meeting as a manager?
Start with questions about the work and obstacles, then team dynamics, growth and how well they understand the organization's direction. Ask about their manager in a balanced, forward-looking way.
What questions should an employee ask in a skip level meeting?
Ask about department priorities, upcoming challenges, the skills that will matter in your role and what great performance looks like from the leader's point of view.
How often should skip level meetings happen?
Quarterly is common for one-on-ones. Large frontline operations often run group sessions monthly, rotating through teams and shifts so everyone attends about once a quarter.
Are skip level meetings confidential?
Leaders usually share themes, not names, with middle managers. Confidentiality has limits: concerns about safety, harassment or legal violations must be escalated through proper channels.
How long should a skip level 1 on 1 be?
20 to 30 minutes is typical for one-on-ones, and 45 to 60 minutes for a small group session.