A skip-level meeting is a conversation between a senior leader and someone who reports to one of their direct reports. It bypasses one layer of management, not to undermine the middle manager, but to give senior leaders a clearer view of what is really happening on the ground. When done well, skip-levels build trust across levels, surface issues that might otherwise be filtered out, and give individual contributors a voice they rarely get in day-to-day operations.
The most valuable thing a skip-level meeting produces is not information for you. It is the feeling, for the person across the table, that someone senior genuinely cares about their experience and perspective.
Why skip-levels matter
As organisations grow, the distance between senior leaders and the people doing the work increases. Information gets filtered, summarised, and sometimes unintentionally distorted as it moves up the chain. Skip-level meetings close that gap and give you access to perspectives that would otherwise never reach you.
- Unfiltered perspectiveEven the best middle managers unconsciously filter what they pass upwards. They may downplay problems they are working on or highlight successes more than struggles. Skip-levels give you a direct line to how things actually feel on the ground.
- Early warning systemProblems with culture, process, or morale often show up at the team level long before they become visible to senior leadership. Regular skip-levels help you detect issues early, when they are still manageable rather than entrenched.
- Talent visibilitySkip-levels let you see high-potential people who might otherwise be invisible to you. Understanding who your rising talent is, what motivates them, and what they aspire to helps you make better decisions about development and succession.
- Trust across levelsWhen people feel that senior leaders are accessible and genuinely interested in their work, engagement increases. It signals that the organisation values people at every level, not just those closest to the top.
Preparing the ground
Skip-level meetings can feel threatening to the middle manager if handled poorly. They may worry that you are checking up on them or gathering ammunition. Preparation is essential, both with the manager whose team you are meeting and with the individuals themselves, to ensure the process builds trust rather than eroding it.
- Brief the middle managerBefore scheduling any skip-levels, talk to your direct report about what you are doing and why. Be transparent about your intentions. Reassure them that the goal is to stay connected to the wider team, not to evaluate their management. Share what you learn afterwards where appropriate.
- Explain the purpose clearlyWhen you invite someone to a skip-level, explain what it is and what it is not. Many people will feel nervous about meeting with their boss's boss. Make it clear that the conversation is informal, that there is no hidden agenda, and that you are genuinely interested in their perspective.
- Prepare thoughtful questionsDo not wing it. Prepare a handful of open questions that invite honest reflection. "What is working well on your team?" and "If you could change one thing about how we work, what would it be?" are far more productive than "how are things going?"
- Schedule with careKeep skip-levels to thirty minutes or less. Schedule them during normal working hours at a time that is convenient for the other person. Making someone rearrange their day for a meeting they did not ask for sends the wrong message from the start.
Running the meeting
The meeting itself should feel like a conversation, not an interview. Your role is to listen far more than you talk. The person sitting across from you may be nervous, guarded, or unsure what you want to hear. Your job is to make the space safe enough for them to be honest.
- Start with warmthBegin with something personal and low-stakes. Ask about their background, what they enjoy about their work, or what they have been working on recently. This helps the person relax and sets a conversational rather than interrogative tone.
- Ask, then listenAsk your prepared questions and then give the person space to answer fully. Resist the urge to fill silences or steer the conversation. Some of the most valuable insights come after a pause, when the person decides to share something they were not sure they should say.
- Do not solve on the spotIf someone raises a problem, do not immediately jump to fixing it. Thank them for sharing, ask clarifying questions, and explain what you will do with the information. Making promises you cannot keep or overriding their manager in the moment creates more problems than it solves.
- Respect boundariesIf someone is clearly uncomfortable discussing a topic, do not push. Some people need multiple skip-levels before they trust the process enough to be fully candid. Build the relationship gradually and the openness will follow.
Acting on what you hear
The fastest way to destroy the value of skip-level meetings is to do nothing with the information you receive. If people share honest feedback and nothing changes, they will stop being honest. Acting on what you hear, even in small ways, builds credibility and encourages ongoing candour.
- Identify patternsA single comment from one person is an anecdote. The same theme appearing across multiple skip-levels is a signal. Look for patterns in the feedback you receive and prioritise systemic issues over individual gripes.
- Route feedback appropriatelySome feedback should go to the middle manager, some should inform your own decisions, and some may need to go to other parts of the organisation. Be thoughtful about where each piece of feedback goes and protect confidentiality where you promised it.
- Close the loopWhen you take action based on skip-level feedback, let people know. You do not need to attribute it to a specific person, but saying "based on feedback from the team, we are changing X" shows that the conversations led to real outcomes.
- Keep the cadenceRun skip-levels on a regular schedule, whether quarterly or twice a year. Consistency signals commitment. If you only do them once and then stop, people will assume it was performative. Regular cadence builds the trust that makes the conversations genuinely useful.
Capture every conversation
Record meeting notes, track themes, and follow up on actions so that insights from skip-levels turn into meaningful change.