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Senior leaders and managers

Leadership Retreat Bingo

A reflective icebreaker bingo for leadership retreats and strategy offsites.

Leadership Retreat Bingo is built for offsites where leaders step away from daily operations to think strategically and connect with peers. It encourages genuine conversation about leadership experiences, working styles, and priorities, rather than small talk about the weather. It works well as an opening activity before the main retreat agenda begins.

How to run this activity

Give each leader a bingo card at registration or during the welcome session of the retreat. Participants circulate the room, having short conversations to find colleagues who match each square and noting their name. Allow enough time for meaningful exchanges rather than rushed ticking, ideally with refreshments on hand. Bring the group together afterwards to share a few of the more interesting matches found.

Full prompt list

  1. Find someone who has led a team through a major change
  2. Find someone who mentors a colleague outside their team
  3. Find someone who started in a completely different role
  4. Find someone who has led a team of more than fifty people
  5. Find someone who has a leadership book they often recommend
  6. Find someone who has worked in more than one industry
  7. Find someone who values feedback from their team highly
  8. Find someone who has led a team through a difficult project
  9. Find someone who has hired someone in the last six months
  10. Find someone who started their career in a very different field
  11. Find someone who has worked internationally
  12. Find someone who has led a successful cross-team initiative
  13. Find someone who has a favourite leadership quote or principle
  14. Find someone who has coached a colleague into a promotion
  15. Find someone who values one-to-one conversations with their team
  16. Find someone who has led during a period of significant growth
  17. Find someone who has navigated a difficult team restructure
  18. Find someone who champions a specific value at work
  19. Find someone who has represented the organisation externally
  20. Find someone who has led a project outside their usual expertise
  21. Find someone who has an idea for improving team communication
  22. Find someone who has attended a leadership retreat before
  23. Find someone who has a clear personal leadership philosophy
  24. Find someone who has recently celebrated a team success

Customisation ideas

  • Add prompts referencing your organisation's specific strategic priorities
  • Adjust for a mixed group of internal leaders and external partners
  • Pair with a longer reflective discussion once cards are complete
  • Include a prompt about a leadership book or resource people recommend

Frequently asked questions

The prompts are written around leadership experience, decision-making, and management style rather than general hobbies, making conversations feel more relevant to a senior audience. It respects that leaders often want substance even in an icebreaker.

Yes, even familiar colleagues often have not discussed some of these specific experiences, so it can surface new perspectives among people who work together regularly. It shifts the conversation beyond usual meeting topics.

Yes, it works well at cross-organisation retreats or partner events, since the prompts focus on shared leadership themes rather than internal company specifics. It gives external attendees an easy way in too.

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