Skip-Level Meetings: 30 Questions and the Format

When the CEO of a mid-size 600-person company suddenly decides to hold hour-long meetings with twenty employees from different teams — without their direct managers present — the team's reaction is usually the same. "Something's wrong." "There'll be layoffs." "The CEO is planning a reorg." This is the typical reaction to a format called a skip-level meeting — a meeting with someone one rung down the hierarchy. And that reaction is the main sign that the format isn't being used right in the company.

A skip-level is a meeting between a senior leader (a CEO, a department head) and an employee who doesn't report to them directly (but to their direct report). It's not "undermining the hierarchy" and not "escalating over someone's head." It's a tool for taking the temperature of a team that, applied correctly, gives a senior leader information you can't get from quarterly reports and engagement surveys.

This article is a practical breakdown of the format. When it's appropriate, how to structure it, thirty questions in six categories, which anti-patterns kill trust, and how to record results so you don't expose either the employee or their manager.

What a Skip-Level Is and When It's Appropriate

The simplest definition. A skip-level is a direct conversation between a senior leader and an employee, across one management rung. A CEO with an engineer, a department head with a junior analyst, a head of product with a designer.

What distinguishes a skip-level from a regular 1:1:

• The employee's manager knows about the meeting (this is critical — more below).
• The goal isn't to give the employee feedback (that's their manager's job), but to learn about their experience, observations, and ideas.
• Confidentiality by default: what was discussed isn't passed to the manager in identified form.
• The rhythm isn't weekly, but once every 6–12 months per employee.

Why it's needed. A few typical tasks a skip-level addresses:

Information past the filters. Every management layer in a company is a filter. What reaches the CEO has passed through 2–3 rungs of managers, each of whom, wittingly or not, has filtered out the "difficult," the "awkward," the "not relevant." Through a skip-level, the CEO gets access to unfiltered information.

Developing leaders. A skip-level helps a senior leader see which of their reports are becoming genuine leaders for the team and which are leaders in title only. This isn't a way to "evaluate" a manager behind their back — it's a way to spot strong leaders for future growth.

A signal of attention. When a CEO regularly talks with employees 2–3 levels down, it's a signal that the company isn't run solely through the top team. Employees understand: they're seen, their experience matters. This strengthens trust in the organization.

Early detection. Problems that take 3–6 months to appear in engagement surveys surface immediately in a skip-level. The CEO leaves the meeting with a concrete "team X has this problem" — and starts looking into it before it becomes a crisis.

Is a skip-level appropriate in your company? A few markers.

Appropriate if:

• The company has more than 100 people (on a smaller sample the format is overkill).
• The CEO/directors have time for it — an hour a month at minimum.
• The culture assumes that a direct conversation is normal, not scary.

Not appropriate if:

• The company has fewer than 50 people — the CEO already crosses paths with everyone weekly.
• The culture is strongly hierarchical ("going over someone's head" is seen as undermining).
• A skip-level is being held for the first time in a crisis (layoffs, restructuring) — the format will be associated with a threat and won't work.

Six Categories of Skip-Level Questions

Thirty questions in six groups. You don't need to ask all 30 — pick 5–7 per meeting from different categories, depending on what you want to learn.

The full list of thirty questions.

Category 1. Role context — what the person does and how they feel.

1. Tell me what you're working on right now — no job title, in your own words.
2. What's changed in your work over the last six months?
3. What gives you the most energy right now?
4. What in your role would you like to do more of, and what less?
5. If you could pick one project currently running in the company that you'd want to be part of, which would it be?

Category 2. Processes and tools — what gets in the way.

6. What in our processes gets in the way of working effectively?
7. Which three processes should be simplified or removed?
8. What's missing in the tools you use?
9. Where do we waste time — what do you see from the inside?
10. If I could remove one management ritual meeting from your week, which would you pick?

Category 3. Development and career.

11. Where do you see yourself in the company in two years?
12. What's missing right now for your growth?
13. Which skill would you like to develop over the next year?
14. Do you get enough feedback on your work?
15. What would help you feel you're growing faster than you are now?

Category 4. Culture and relationships.

16. What in our culture works well — what would you not want to change?
17. What would you change in our culture if you could?
18. Do you feel your opinion is heard here?
19. Who in the company is easy to work with, and who's hard? (no names, by type of interaction)
20. Has there been a time you wanted to raise an important topic and didn't — why?

Category 5. Open questions — what the person wants to say.

21. What would you want me to know but fear I won't ask?
22. If you could change one decision we made in the company over the last year, which would it be?
23. What do you think about at work that you don't bring to meetings?
24. What matters to you beyond work tasks?
25. What would you ask me if there were no "political" considerations?

Category 6. The manager topic — the most delicate.

26. What about working with your manager works especially well?
27. Where does your manager help you grow?
28. What, in your view, should they do more of for the team?
29. What should they do less of?
30. Would you want me to change anything I ask of your team?

Category 6 is the most sensitive. Move to it only at the end of the conversation, once trust is established. And definitely state up front: nothing from the answers will reach the manager in identified form.

Skip-Level Anti-Patterns

A few traps that reliably kill the format — sometimes for good.

Not telling the manager. The most common and most destructive anti-pattern. The CEO meets with an employee; the manager finds out by accident two days later. Within two months the manager feels "bypassed" and starts playing political games. A skip-level must be fully transparent to the employee's manager: "I plan to meet each of your people once every six months, this isn't an evaluation of you, it's taking the temperature." Without that, there's no format.

Revealing who said what. If, after a skip-level, the employee's manager can guess that their report said something critical, the format is dead. No one will speak honestly anymore. Information is passed to the manager only in aggregate: "the team has a workload theme" — yes; "Ivan complained about workload" — never. If, on a team of 5, one theme can only be attributed to one person, it's better not to voice that theme to the manager at all.

Using it as a tool to evaluate the manager. If, after a skip-level, the CEO goes to the manager with "here's what they told me about you," that sabotages trust both in the CEO and in the format. A skip-level is for information and signals, not for evaluation. Evaluating the manager is a separate process, through the performance review and the CEO's regular 1:1s with the manager themselves.

Promising actions and not delivering. If an employee raised a problem in a skip-level and the CEO said "we'll look into it" — and a month later nothing happened — that undermines trust more than if the meeting had never happened. Better to honestly say "this is an interesting topic, I'm not sure we can do something about it quickly right now; let me come back to it in 60 days with a concrete answer."

Doing it only in a crisis. If a skip-level is held for the first time amid layoffs or restructuring, the format will be associated with a threat. Employees will come cautiously, answer perfunctorily, and there'll be no trust. A skip-level should start in calm times so it becomes a norm — and then in a crisis it works as a valuable tool.

How to Record It Without Undermining Trust

The final detail — what to do with what you learned in a skip-level. A few rules.

Notes — for yourself, not published. The CEO's personal notes on the meeting go nowhere. Not into the HR system, not to the manager, not into a shared channel. It's one person's working notebook.

Aggregates — published. Once a quarter or half-year, the CEO publishes an aggregated report: "from the skip-level meetings this quarter, these common themes are visible." No names, no details, no team identification if teams are small. This turns the skip-level into a visible format, not a hidden one.

Concrete actions — tied to the theme, not the person. If you decided, off the back of a skip-level, to launch a review of the evaluation process, communicate it in a shared channel as your management decision, without referencing "we were told in a skip-level." The employee who raised the theme may recognize their own "authorship," but no one else will.

Passing it to the manager — only with the employee's explicit consent. If a skip-level surfaced a problem that needs to be solved at the level of the direct manager, and the employee is ready to talk to them, encourage it. But if they're not ready, don't go to the manager with that topic behind the employee's back. This rule can't be broken.

The Bottom Line

A skip-level meeting is a format for a direct conversation between a senior leader and an employee one rung down. Applied correctly, it's a powerful tool for taking the temperature of a team and accessing information past management filters. Applied wrong, it's a fast way to destroy trust both in the CEO and in the format itself.

Thirty questions in six categories — not as a questionnaire, but as a menu you pick 5–7 from per meeting. The categories: role context, processes, development, culture, open questions, and (gently) the manager topic.

The main rules: warn the manager in advance, keep confidentiality strict, pass things along in aggregate, deliver on promised actions. Without these, the format dies within two cycles.

And finally — a skip-level complements, not replaces, managers' regular work with their teams. If a CEO starts skip-leveling because their managers "don't understand anything," that's a signal the problem is in the management layer, not in the information channels. Treat the problem, don't paper over it with a workaround.

If you'd like the map of thirty questions on a single page, it's at the link in the card. No signup — copy it and take it to your meetings.

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If your company is building out a skip-level format and you need a second pair of eyes on the structure, write to us — we'll discuss it in an hour-long call.

The TeamEvo Team. We write about company culture, HR tech, and AI without the hype.

Where the follow-ups from these meetings live: performance review.