A skip-level meeting is a conversation between a senior leader and an employee who does not report directly to them — skipping the layer of management in between. The manager’s manager sits down with one of the manager’s direct reports, without the manager present.
The purpose is information. Senior leaders are structurally insulated from what is happening at the team level — information travels upward through layers of management, and at each layer it is filtered, softened, reframed, or simply lost. Skip-level meetings are one of the few mechanisms for cutting through that insulation and hearing what is actually true about the team’s experience, the manager’s effectiveness, and the cultural health of the organisation.
Done well, a skip-level meeting is one of the most valuable conversations a senior leader can have. Done poorly — with the wrong questions, poor follow-through, or a breach of the confidentiality implied by the format — it damages trust, undermines the manager, and produces worse outcomes than not having the meeting at all.
This guide covers 30 specific skip-level meeting questions, what to listen for in the answers, and what to do with what you learn.
What is a skip-level meeting?
A skip-level meeting is a structured conversation between a senior leader and an employee one or two levels below them in the organisation — bypassing the direct manager who sits between them. The name describes the structure: the leader skips a management level to speak directly with someone further down the reporting chain.
Skip-levels serve a specific diagnostic purpose. A manager’s direct reports see things the manager cannot see about their own behaviour, their management style, the team’s actual morale, and the gap between what the manager reports upward and what is actually true on the ground. Skip-level meetings surface this information in a way that nothing else quite replicates.
They are commonly used for three purposes. First, as a regular practice — senior leaders hold skip-level conversations with all employees below them on a quarterly or semi-annual basis, as part of a systematic effort to maintain direct knowledge of what is happening in the organisation. Second, as a diagnostic — when a manager or team is flagged for performance or cultural concerns, skip-level conversations help the senior leader understand the situation from multiple perspectives before acting. Third, as a retention tool — conversations with high performers who may be at risk of leaving, where hearing their perspective directly signals that senior leadership notices and values them.
Skip-level meeting questions — 30 organised by topic
Setting up the conversation
Before asking any substantive questions, spend two to three minutes establishing what the conversation is for. Without this framing, employees will typically default to safe, polished answers designed to avoid saying anything that could reflect poorly on their manager or themselves.
Say something like: “The purpose of this conversation is for me to understand what it’s actually like to work on this team — not to evaluate you or your manager, but to make sure I’m not missing anything important from where I sit. Everything we talk about stays with me unless you explicitly ask me to act on something.”
This framing is not a script — adapt it to your voice. But it needs to communicate three things: that you are here to listen rather than to evaluate, that there are no wrong answers, and that you will handle what you hear with discretion.
On day-to-day work and team health
“What part of your work do you find most energising right now, and what is taking the most out of you?”
This question surfaces both motivation and friction without requiring the employee to frame anything as a complaint. The answer tells you whether the workload is right-sized, whether the role is well-matched to the person, and whether there are structural issues that are draining energy.
“What is the thing that most slows you down or makes your work harder than it needs to be?”
Often produces the most actionable information in the conversation. Employees rarely raise process, tooling, or coordination problems in their normal 1:1s because they have adapted around them. The skip-level format — with someone who can actually change things — creates the context to name them.
“How would you describe the mood on the team right now — and what’s driving it?”
The question behind the question: is morale high or low, and does the employee have a theory about why? Their answer tells you both the current state and the perceived cause, which is significantly more useful than just the state.
“Is there anything the team is consistently struggling with that you don’t feel is getting addressed?”
Surfaces unresolved problems that employees have learned not to raise because previous attempts went nowhere. The phrase “consistently” signals you are asking about patterns, not one-off incidents.
“What would make the biggest difference to how the team works together?”
A forward-looking question that produces constructive input rather than complaint. Often surfaces interpersonal dynamics, communication patterns, or missing resources that the manager has not noticed or has not been able to fix.
On the manager
Questions about the manager require the most care. Frame these as questions about the employee’s experience rather than requests for a manager evaluation. “How does your manager help you do your best work?” is more likely to produce honest answers than “What do you think of your manager?”
“What does your manager do that you find most helpful?”
Produces genuine positive feedback about the manager’s approach — which is both useful data and a normalising frame that makes the conversation about development rather than evaluation.
“Is there anything your manager could do differently that would help you or the team?”
The softer version of “what is your manager doing wrong.” Employees who have a concern but are hesitant to be direct often answer this question more honestly than anything more explicit.
“How often do you have meaningful conversations with your manager about your development and career?”
Frequency here is a proxy for quality. “Every two weeks” covers a wide range of conversation quality; following up with “and what do those conversations typically cover?” produces more useful information.
“Do you feel like your manager knows what you’re working on and what’s getting in your way?”
Measures managerial visibility without directly asking whether the manager is paying attention. If the answer is no, the follow-up question — “what would help with that?” — often surfaces a specific and fixable problem.
“When you have a concern or an idea, do you feel comfortable raising it with your manager?”
Psychological safety question framed through the specific relationship. If the answer is qualified or no, explore what has made raising things feel unsafe — without pressing in a way that puts the employee at risk.
On culture and inclusion
“Do you feel like your contributions are recognised and valued on this team?”
Direct recognition question. The answer tells you whether the team’s appreciation culture is functioning and whether this specific person feels seen. If the answer is no, the follow-up is whether this feels specific to them or more broadly true on the team.
“Are there people on the team whose work you feel goes consistently unrecognised?”
Often produces the most honest answers because it asks about others rather than the employee themselves. People are more comfortable naming colleagues who are invisible than naming themselves as underappreciated.
“When someone on the team does something excellent, how does that typically get acknowledged?”
Behavioural question that reveals how recognition actually works day-to-day — not what the policy says but what actually happens.
“Do you feel like everyone on this team is treated fairly — that the same standards apply to everyone?”
Fairness is often the underlying theme behind complaints about culture, management, and morale. This question names it directly.
“Is there anything about the way the team operates that makes it harder for some people to succeed than others?”
Inclusion question that surfaces structural or cultural patterns the employee may have observed even if they are not personally affected by them.
On communication and direction
“How clear are you on what the team’s priorities are for this quarter?”
Clarity of direction is one of the most consistently under-addressed management problems. Many employees operate in genuine uncertainty about what matters most, adapting by defaulting to whatever their immediate task list says.
“Do you feel like you understand how your work connects to what the company is trying to achieve?”
Purpose and line-of-sight question. When the answer is vague or negative, it often reflects a communication failure at the leadership level rather than a lack of effort on the employee’s part.
“When big decisions are made that affect your work, do you feel like you are kept informed in a reasonable way?”
Communication quality question that surfaces whether employees feel like they are discovering important changes late, through informal channels, or in ways that create uncertainty.
“Is there information you feel you need to do your job well that you are not currently getting?”
Practical question that often produces specific, actionable answers — the dashboard they do not have access to, the context about a client relationship that nobody shares, the engineering decision that keeps changing direction.
“When priorities change, how do you usually find out — and how long after the decision was made?”
Measures the lag between a decision and the people affected by it. A long lag, or “from a colleague” rather than “from my manager”, points to where communication is breaking down — and it is usually a process problem rather than a personal one.
On growth and future
“What are you working on developing in yourself right now, and does your current role give you the opportunity to develop it?”
Development question framed around the employee’s own priorities rather than the organisation’s. The gap between what they want to develop and what their role provides is one of the most common and least-discussed drivers of quiet disengagement.
“What would need to be true for you to still be here in two years, doing work you find genuinely meaningful?”
Retention question framed constructively. The answer tells you both what is currently working and what is missing — which is more useful than asking whether they are planning to stay.
“Is there a type of work you are not currently doing that you would like to take on?”
Often surfaces capability that is going unused — an employee with skills or interests the team needs but that the manager does not know about.
“What would make you more effective in your role? Resources, access, clarity — anything.”
Open-ended question that produces whatever the employee most wants to name. Listen for what they choose first.
“Who here has helped your development the most — and do you think they know it?”
Surfaces the informal mentors and multipliers on the team, who are often invisible in formal reporting. The second half matters: if the answer is no, you have found recognition that is overdue.
On the organisation and senior leadership
“What do you think senior leadership doesn’t fully understand about what it’s like to work on this team?”
The most direct question on this list — and the one most likely to produce the information that is hardest to get through normal channels. Use it toward the end of the conversation, after trust has been established. Some employees will be direct; others will deflect. Both are informative.
“What do you think the organisation does particularly well that we should make sure we protect?”
Positive question that surfaces what employees value — which tells you what to be careful not to disrupt in any future changes.
“If you could change one company-wide decision or policy, what would it be?”
Moves the conversation beyond the team to the wider organisation. Employees often have a clear view of which policies create friction in practice — even when those policies made sense on paper.
“Is there anything you wish you could tell someone at my level that you haven’t been able to?”
The catchall question. Some employees will say no. Others will have been waiting for exactly this question. Either way, it signals that you are genuinely open to hearing what is hard to say.
“What is one thing I could do differently that would make your experience at this company better?”
Turns the dynamic: rather than only gathering information about the manager and team, this asks the employee to give feedback to the senior leader directly. It is both informative and a powerful signal of genuine humility.
What to listen for beyond the words
What gets volunteered versus what requires prompting. The things an employee says before you ask a specific question are the things that are most on their mind. If someone immediately mentions a colleague who is struggling, that is more significant than if they mention it only after you ask explicitly.
Qualifications and hedges. “I think most people are happy” or “it’s generally fine” are not the same as “people are happy” or “it’s fine.” Hedges signal either genuine uncertainty or reluctance to be more direct. Follow up with “what makes you say most people?” or “what would fine look like versus great?”
What is not mentioned. If you spend thirty minutes with someone who never mentions their manager at all, that absence is information. If a team member never talks about career development despite you asking multiple questions that open the door for it, pay attention to that gap.
Energy shifts. When a topic produces noticeably less or more energy — a quicker answer, a shift in posture, a longer pause than usual — that is a signal to either explore further or to give space for the employee to choose how much they share.
Patterns across multiple conversations. A single employee mentioning something is an observation. Three employees independently mentioning the same thing without being prompted is a pattern that warrants action.
What to do with the answers — and what not to do
What to do
Close the loop. Tell the employee before the meeting ends what you will and will not act on from the conversation. “I’m going to think about what you said about the priority communication — that’s something I can influence. The process issue you mentioned is better addressed through [manager] — are you comfortable with me raising it without attributing it to you?”
Share themes, not sources. When you act on information from skip-level conversations, act on the pattern rather than the specific statement. “I’m hearing from several people that direction gets unclear mid-quarter” is different from “someone told me they’re confused about priorities.” The first produces change; the second produces a search for the source.
Follow up. A skip-level conversation that produces no visible change is worse than no skip-level conversation. It signals that the process is theatre. Even a brief email two weeks later — “I wanted to let you know I’ve been thinking about what you mentioned about X and here’s what I’ve done about it” — demonstrates that the conversation had real value.
What not to do
Do not immediately relay specifics to the manager. If an employee shares something about their manager’s behaviour in confidence, going directly to the manager with “your direct report told me X” destroys the trust that made the conversation possible. Act on the information systemically; discuss the theme with the manager; don’t betray the source.
Do not promise action on things you cannot change. If an employee raises a structural issue that is above your authority or outside your scope, say so rather than implying you will act and then not following through.
Do not conduct skip-levels only when there is a problem. If the first time employees hear from their manager’s manager is during an investigation or a restructure, the format carries the wrong signal. Regular skip-levels normalise the practice and make the conversations more honest.
How often should skip-level meetings happen?
For a senior leader with two to four managers below them, each with teams of five to eight people, a reasonable cadence is quarterly one-on-ones with each direct report’s team — meaning the senior leader speaks with each team member two to four times per year.
For larger organisations this is not always practical. In those cases, prioritise: hold skip-levels with high-performers who may be flight risks, with employees in newly formed or struggling teams, and with employees who have not been visible in broader company conversations and may be underserved by the current management structure.
Even one skip-level conversation per quarter with a randomly selected employee provides more ground-level information than none — and signals to the whole organisation that senior leaders are interested in what is actually happening.
When skip-levels don’t work — and what to use instead
Skip-level meetings have real limitations. They are time-intensive for senior leaders. They create the perception of surveillance for managers who have not been involved in designing the process. They rely on employees being willing to be candid in a conversation with someone senior — which many are not, particularly in cultures where raising concerns has historically been unsafe.
And they are slow. A senior leader can have ten or twenty skip-level conversations per quarter. Aggregating honest information about team health across a larger organisation at meaningful frequency requires something more scalable.
Anonymous pulse surveys solve several of these problems simultaneously. Run on a monthly or quarterly cadence, an anonymous survey asks every employee in a team or organisation the same questions at the same time. The anonymity removes the social risk of being candid with someone senior. The scale makes it possible to identify patterns across the whole organisation rather than the small sample that skip-level meetings reach. And the regularity creates trend data — not just what people think right now but how that has changed over time.
Karma’s anonymous feedback feature runs pulse surveys directly in Slack — three to five questions delivered to the whole team, responses submitted anonymously, aggregated results visible to managers and senior leaders in the dashboard. The questions can cover the same topics as a skip-level meeting: team health, manager effectiveness, recognition, clarity of direction, and inclusion. The data is available within hours rather than weeks, covers everyone rather than a selected few, and carries no social risk for the respondents.
The combination works well: skip-level conversations for depth and relationship, anonymous pulse surveys for breadth and frequency. Skip-levels tell you what one person thinks, with the nuance and context that comes from a real conversation. Pulse surveys tell you what everyone thinks, at scale, without the bottleneck of one-on-one scheduling.
See how Karma’s anonymous feedback feature works →
FAQ
What is a skip-level meeting? A skip-level meeting is a conversation between a senior leader and an employee who does not report directly to them — bypassing the layer of management in between. The purpose is for the senior leader to hear directly from people further down the reporting chain, without the filter of middle management. Skip-level meetings surface information about team health, manager effectiveness, and cultural issues that typically do not make it through normal reporting channels.
What should I ask in a skip-level meeting? The most useful skip-level questions ask about the employee’s experience rather than requesting evaluations of others. Focus on what energises and drains them in their work, whether they feel their contributions are recognised, how clear they are on team priorities, whether they feel safe raising concerns, what gets in the way of doing their best work, and what they wish senior leadership understood about their experience. Questions framed as “what does your manager do that helps you?” produce more honest answers than “how is your manager doing?”
How do you run a skip-level meeting effectively? Begin by framing the purpose — explain that the conversation is for information, not evaluation, and that you will handle what you hear with discretion. Ask open questions rather than yes/no questions. Listen for what gets volunteered versus what requires prompting, and for qualifications and hedges that signal something is not being said directly. Close by telling the employee what you will and will not act on from the conversation. Follow up within two weeks with any actions you have taken.
How often should skip-level meetings happen? For most organisations, quarterly is a reasonable cadence — each team member speaks with their manager’s manager two to four times per year. In larger organisations where quarterly one-on-ones with every employee are not practical, prioritise high-performers at retention risk, employees in struggling teams, and people who have been less visible in broader company conversations.
What is the difference between a skip-level meeting and a 1:1? A 1:1 is a regular meeting between a manager and their direct report. A skip-level meeting is a conversation between a senior leader and someone one or more management levels below them — the direct report’s manager is not present. The purposes differ: 1:1s are primarily for task coordination, feedback, and development within the reporting relationship. Skip-level meetings are primarily for senior leaders to gather information about team health and manager effectiveness that would not otherwise reach them.
What should I do with what I learn in a skip-level meeting? Act on patterns rather than specific statements, to protect the confidentiality of individual conversations. Close the loop with the employee on what you will and will not act on. When feeding information back to the manager in between, share themes rather than specific quotes or sources. Follow up with the employee to show that the conversation had real consequences. Avoid conducting skip-levels only when there is a problem — regular cadence makes the process normal and the conversations more honest.
