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Freedom251 › Blog › employee feedback

How Managers Can Hold Effective Skip-Level Meetings

By Freedom251 Team · · 9 min read

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A skip-level meeting is a periodic one-to-one between an employee and that employee’s manager’s manager. Run well, it gives senior leaders direct context about work, systems and employee experience while giving the employee a credible chance to be heard. It is not a covert assessment of the employee’s direct manager. Its value depends on a clear purpose, psychological safety, attentive listening and visible follow-through.

What a skip-level meeting is—and is not

During a skip-level meeting, an employee periodically meets one-on-one with their supervisor’s manager. The senior leader is one level removed from the employee’s normal reporting line. That distance can reveal information that is filtered, delayed or difficult to raise in ordinary supervision.

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The format is useful for several distinct purposes:

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  • hearing feedback about work, systems and leadership;
  • understanding the employee’s relationship with their direct manager;
  • building connection between senior leaders and the wider team;
  • recognizing achievements and understanding development needs; and
  • gauging how an organizational change is affecting day-to-day work.

A skip-level should not become a secret channel for routine supervision of the direct manager, a performance review of the employee or a promise that the senior leader will personally fix every issue. If the organization needs to investigate misconduct, discrimination, retaliation or another formal complaint, use the established reporting and investigation process.

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Set the purpose before you schedule

Choose one primary objective

Employees answer more candidly when they know why they have been invited. Decide whether this round is primarily for listening during a change, understanding operational obstacles, learning about team health, discussing development or building relationships. You can cover related topics, but a stated priority keeps the conversation from feeling like an unstructured interrogation.

Tell the employee what is in scope and what is not. For example: “I am meeting with people across the team to understand how the new workflow is affecting your work. I also want to hear what support would help. This is not a performance review.”

Assess trust and psychological safety

Trust is a precondition, not an automatic result of the meeting. Consider the existing relationship, recent reorganizations, conflict on the team and whether employees have previously seen leaders act on feedback. If the relationship is new or strained, begin with informal relationship-building and consistent psychological-safety practices before launching a formal program.

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Explain how notes, escalation and follow-up will work. Never promise absolute secrecy unless organizational policy and applicable legal obligations allow it. A precise explanation is safer: “I will keep your comments as private as I can, but I may need to share information with the people responsible for addressing a safety, legal or policy issue. I will tell you what I can about next steps.”

Invite, do not summon

The invitation should identify the purpose, expected length if your organization has set one, participants and the employee’s ability to suggest topics. There is no evidence here for a universal meeting duration. An informal setting such as coffee may suit some employees, but location is a preference, not a proven performance intervention.

Choose a format and cadence deliberately

Direct skip-level evidence recommends periodic conversations but does not establish a universal frequency. Select a rhythm that matches the purpose, team size and capacity to follow through. A recurring program that produces no action is more damaging than a smaller number of carefully handled conversations.

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Design choice When it may fit Risk to manage
One-to-one Personal experiences, development and sensitive concerns The employee may feel exposed if confidentiality and escalation limits are unclear
Group listening session Common workflow, policy or change questions Peer presence can suppress individual concerns; provide another route for private follow-up
Recurring meetings Maintaining connection and spotting patterns over time Routine can become performative if leaders do not act on themes
Change-triggered meetings Reorganizations, new systems, major policy or strategy shifts Employees may interpret the meeting as crisis management or an evaluation
Employee-led agenda Trust-building and broad listening The employee may need prompts to get started
Leader-led agenda A defined operational or change objective Leading questions can steer or narrow the feedback

Evidence about ordinary manager-direct-report one-to-ones can inform, but not determine, a skip-level schedule. In a 2024 Harvard Business Review IdeaCast interview, Steven G. Rogelberg said available evidence generally favors weekly and then biweekly one-to-ones; he cautioned that monthly meetings can suffer recency bias and that meetings more frequent than weekly can feel like micromanagement. He also said research does not establish which location produces the best outcomes. Those observations concern ordinary one-to-ones, not a proven skip-level formula.

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Rogelberg’s advice also applies to agenda ownership: “One of the greatest predictors we have of one-on-one meeting success is the direct either creating the agenda themselves or doing it in concert with the leader.” In a skip-level, give the employee meaningful control while supplying a short list of optional prompts.

Prepare without scripting the employee

  • Review the stated objective, current organizational changes and known constraints.
  • Check whether the employee has recently raised an issue through another channel so you do not ask them to repeat it unnecessarily.
  • Prepare three or four open prompts, not a questionnaire that must be completed.
  • Decide what information you can share about priorities, decisions and constraints.
  • Plan how you will record themes without creating a misleading verbatim record.
  • Identify the correct owner for likely follow-up: you, the direct manager, human resources, compliance, safety, information security or another function.

Rogelberg’s concise framing is useful: “The first thing that managers need to know is that this meeting is for their directs.” In practice, that means the employee’s experience and priorities should determine most of the conversation.

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Run the conversation step by step

  1. Open with purpose and boundaries. Explain why you scheduled the meeting, what you hope to learn, how notes will be used and the limits of confidentiality. State that the employee does not need to arrive with a polished proposal.
  2. Start broad. Ask, “How are things going for you and your team right now?” Then pause. Do not fill the silence or defend the organization after the first concern.
  3. Listen before stating your view. A federal Office of Inspector General report notes that employees may be more willing to share views when leaders solicit input before sharing their own. Reflect what you heard and ask whether you understood it correctly.
  4. Explore the day-to-day work. Ask about workload, obstacles, tools, handoffs, decision rights, priorities and collaboration with other teams. This keeps the meeting focused on systems and work rather than turning it into a referendum on one person.
  5. Discuss the reporting relationship carefully. Ask how the relationship with the direct manager is working, what support helps the employee succeed and where guidance could improve. Request specific situations and effects, while avoiding a demand for a verdict about the manager’s character.
  6. Ask about development and support. Discuss skills or experiences the employee hopes to gain, access to feedback, and one action a senior leader could take to support the employee and team.
  7. Invite concerns that are not fully formed. Say explicitly that the employee may raise an observation or worry without having a complete solution. Expectations that employees formulate an entire idea before speaking can delay escalation.
  8. Check the priority. Near the end, ask which issue matters most and what a useful next step would look like from the employee’s perspective.
  9. Close with an accurate recap. Summarize themes, distinguish facts from interpretations and confirm what you will do, what another owner must do and what cannot be promised.

Open-ended prompts to adapt

  • “What’s been the most rewarding part of your role recently?”
  • “What challenges are you or your team currently facing?”
  • “What’s one thing your manager does really well that helps you succeed?”
  • “Are there areas where your manager could provide more support or guidance?”
  • “Where can team priorities be better aligned?”
  • “How would you describe the dynamics within your team?”
  • “What skills or experiences are you hoping to gain within the next year?”
  • “What’s one thing I, as a senior leader, can do to support you and your team?”

Handle criticism, allegations and confidentiality responsibly

Constructive criticism about a manager belongs in the conversation when it helps explain the employee’s work experience. Keep the inquiry behavior-based: what happened, when, who was affected, what the consequence was and what support is needed. Do not encourage employees to collect evidence against a manager or assure them that a particular outcome will follow.

If the employee describes a possible policy violation, threat, harassment, discrimination, retaliation, fraud or safety risk:

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  • thank them for raising it;
  • clarify immediate safety needs and whether anyone is at risk;
  • explain that you may have to share the information with the responsible function;
  • record only necessary, factual information; and
  • use the organization’s normal reporting and investigation process.

If the issue is a routine workload, prioritization or communication problem, agree whether the employee wants you to raise it directly, whether the direct manager should be involved, and what privacy the employee needs. Do not attribute a comment by name to the employee without permission unless policy or law requires disclosure.

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Close the loop after the meeting

  1. Write a concise record. Capture themes, examples, decisions, owners and dates. Avoid labels, speculation and unnecessary personal details.
  2. Separate ownership. Mark which actions you own, which belong with the direct manager and which require another process. This prevents the senior leader from becoming an unaccountable shadow manager.
  3. Agree on communication. Tell the employee when and how you will update them. If you cannot provide details because of privacy or an investigation, say so plainly.
  4. Act or explain. When a suggestion is not adopted, explain the rationale, constraints or alternative. The OIG report warns that unexplained decisions can reduce employees’ future willingness to share views.
  5. Follow up. Revisit the agreed issue at the promised time. A listening invitation without credible follow-through undermines trust.
  6. Look for themes, not personal scorecards. Across meetings, aggregate recurring barriers and system failures. Share patterns in a way that protects individual employees and does not turn comments into a covert evaluation of a direct manager.

Common failure modes and fixes

Failure mode What employees experience Correction
Surprise invitation with no purpose Anxiety and speculation about performance State the objective, scope and expectations in advance
Leading questions Pressure to confirm the leader’s preferred story Start broad, then ask neutral follow-ups
Defending the organization too early The concern is dismissed before it is understood Listen, reflect and clarify before explaining
Promising absolute confidentiality Loss of trust when escalation is required Describe privacy practices and mandatory limits accurately
Only asking about the direct manager The meeting feels like surveillance or a trap Cover work, systems, collaboration, priorities and development
Demanding a finished solution Early warnings remain unspoken Invite observations and partial ideas
No visible action Employees conclude that speaking up is pointless Assign owners, dates and explanations for decisions
Turning the senior leader into a shadow supervisor Conflicting instructions and bypassed accountability Route routine supervision back through the normal manager while addressing systemic issues

What the available evidence can—and cannot—show

The strongest direct procedural guidance here comes from the University of South Carolina HR guidance and a federal OIG report. They describe intended uses and practical behaviors, not controlled trials proving that skip-level meetings cause better performance, engagement or retention.

Gallup reported that only 15% of employees whose managers did not meet with them regularly were engaged, while employees whose managers met with them regularly were almost three times as likely to be engaged. The result comes from a Gallup Panel Web study of 8,287 employed U.S. adults in the United States, fielded September 4–October 9, 2013 and published August 5, 2014. It concerns manager meetings generally; it does not establish that skip-level meetings caused engagement.

The University of South Carolina guide also repeats figures attributed to Gallup (2022), the Edelman Trust Barometer (2023) and Harvard Business Review (2021): 37% more likely to feel motivated and committed, 82% believing senior leaders should interact more frequently to demonstrate transparency, and 25% more likely to identify operational challenges early. The guide does not provide enough underlying methodological detail to independently verify those figures here, so they should be treated as secondary, directional claims rather than standalone proof.

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A practical invitation and note template

Invitation

“I’d like to meet for a skip-level conversation to understand how your work and team are going, what obstacles you are seeing, and what support would help. This is a listening conversation, not a performance review. Please bring any topics you want to discuss; I’ll also have a few optional prompts. I’ll explain how I handle notes and follow-up at the start.”

Notes

  • Purpose: the stated reason for this meeting
  • What is working: specific strengths, practices or outcomes
  • Barriers and effects: observable issue, impact and affected work
  • Development or support requested: employee’s preferred outcome
  • Confidentiality or escalation limits discussed: what was explained
  • Actions: owner, next step and date
  • Follow-up: when and how the employee will hear back

Bottom line

Effective skip-level meetings are structured listening, not managerial surveillance. Define a purpose, establish realistic privacy expectations, let the employee shape the agenda, ask about work and systems as well as the reporting relationship, listen before offering your view, and document and deliver the follow-up you promise. The meeting earns trust only when employees can see what their candor changed—or understand honestly why a change was not possible.

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employee feedbackLeadershipManagementpsychological safetyskip-level meetings

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