Skip-level meetings are meetings where the boss-of-your-boss meets with you and your team mates, without your direct boss in the meeting. The purpose of skip-level meetings is for higher-level executives to hear more about what’s going on in “the frontline”, to identify possible misalignment and misunderstanding, and to improve their coaching of the person managing the team (i.e. your boss).

Best practice for skip-level meetings

These best practices are written towards the boss-of-the-boss, e.g. the CEO who wants to start organizing skip-level meetings with each of the functional departments in the company.

  1. Meet with entire team below your direct report at once. Direct report is not in the room but you’ll brief him/her in your next 1-1.
  2. Frequency: ~1 team every month, so with ~12 teams each team has their skip-level with you once a year. You can always increase frequency later.
  3. Priority: don’t make any exec feel singled out. Start from random (“Isa will find dates for each team”) or ask if any exec would like their team to go first.
  4. Content/agenda:
    • Promise is you’ll listen but not take any action.
    • Small clarifications are OK but refrain from talking more than ~10% of the time, this is about listening and learning.
  5. Typical questions:
    • “What is everybody working on?” Get a feel for top-of-mind priorities
    • “What is going really well at $Company? What should we keep doing?”
    • “What is not going well at $Company? What should we stop doing?”
    • “What are you missing at $Company? What should we start doing?”
    • Closing (to everybody individually): “if you had a magic wand and you could change just one thing at $Company, what would it be?”

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