Should skip-levels be group or 1:1?

Both, for different purposes. 1:1 for individual signal and connection. Small group (3-6 people from the same or adjacent teams) for team-level dynamics. Group format is efficient for the leader but produces less candid signal than 1:1.

What if a manager objects to skip-levels?

The objection itself is signal — usually the manager is worried what their reports will say. Address directly: 'skip-levels are a normal practice, they're not about evaluating you, and I'll share back any patterns that need addressing. If you're worried about something specific, let's talk about it now.'

How do skip-levels work in a remote company?

Same cadence, video 1:1s. Slightly harder to have the informal moments (coffee, hallway) that surface signal organically, so the meeting itself needs to do more work. Start with a genuinely open question and hold silence long enough for the real answer to emerge.

Skip-Level Meetings: How CEOs and Execs Should Run Them

Skip-level meetings are the single most efficient way for executives to hear ground truth about what's working, what's broken.

Skip-Level Meetings: The 30-Minute Practice That Reveals What Your Managers Won't Tell You

A skip-level meeting is a 1:1 between a leader and someone two or more levels below them in the org — a CEO meeting with an individual contributor, or a VP meeting with a manager's direct report. Done well, they are the highest-signal source of information about how the org is actually functioning. Done badly, they undermine managers and create parallel reporting structures. The difference is entirely in how they're framed and what happens with the information afterward.

Why skip-levels matter

Information degrades as it moves up the org: managers filter, executives summarize, board decks abstract. By the time it reaches the CEO, it's been through 3-4 translations. Skip-levels short-circuit this — you hear the actual words people use to describe their work, the specific things blocking them, the concerns that got polished out of the manager's weekly update. There is no other practice that produces this signal at a comparable time cost.

The right cadence

For a CEO of a 50-200 person company: aim to meet every employee at least once per year, and rotate through in a structured way (e.g., 2-3 skip-levels per week). For an executive with 30-80 people in their org: quarterly with each. Not a fixed reporting relationship — one-off or occasional, so the manager relationship remains primary. Meetings are 30 minutes, informal, on the employee's terms (what's on their mind, not a leader-driven agenda).

How to frame the meeting

Tell the manager in advance ('I'm doing a round of skip-levels this quarter, I'll be meeting with [names]'). Tell the employee the purpose upfront ('I want to hear how things are going from you — what's working, what's frustrating, what you're proud of, what you'd change'). Explicitly not: performance review, chance to escalate around manager, promotion conversation. Explicitly is: your chance to give me signal I don't otherwise get, and my chance to say thank you and share company context directly.

What to do with what you hear

The trust-destroying failure mode: employee shares something specific about their manager, and the manager finds out the next day through a pointed 'coaching moment.' Rule: unless what you heard is a code-of-conduct issue (harassment, discrimination, safety) that must be acted on, treat skip-level content as pattern signal, not individual action items. If three skip-levels in a row surface the same issue, that's actionable. One-off feedback is context, not evidence.

When skip-levels go wrong

Warning signs: your managers feel undermined and begin curating what their reports say to you, skip-levels become de facto performance reviews, employees start expecting them as a regular escalation channel, the leader hears the same 3-4 complaints in every meeting (usually indicating a real systemic issue that needs a different intervention). Fix by resetting the framing publicly, coaching the leader on how to handle sensitive information, and addressing systemic issues at the systemic level.

Frequently asked questions

Should skip-levels be group or 1:1?: Both, for different purposes. 1:1 for individual signal and connection. Small group (3-6 people from the same or adjacent teams) for team-level dynamics. Group format is efficient for the leader but produces less candid signal than 1:1.
What if a manager objects to skip-levels?: The objection itself is signal — usually the manager is worried what their reports will say. Address directly: 'skip-levels are a normal practice, they're not about evaluating you, and I'll share back any patterns that need addressing. If you're worried about something specific, let's talk about it now.'
How do skip-levels work in a remote company?: Same cadence, video 1:1s. Slightly harder to have the informal moments (coffee, hallway) that surface signal organically, so the meeting itself needs to do more work. Start with a genuinely open question and hold silence long enough for the real answer to emerge.

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