Desert Island Questions

Choose this exercise

Purpose: Collect and share individual responses to three hypothetical scenario questions as a low-stakes check-in.

Use it when: At the opening of an informal team retrospective or workshop to start conversation without requiring project disclosures.

Skip it when: When the group needs to resolve serious conflict, make complex decisions, or when time is under ten minutes for a large group.

Group arrangement: Individual silent writing followed by whole-room column review

Timing: Based on the 5-minute writing period from EasyRetro evidence, with 10 minutes allocated for setup, card reading, and debrief.

Materials and tools

• Three sticky notes per person or access to a three-column digital board
• One marker or pen per person for in-person delivery
• Wall space or whiteboard with three taped columns: Best Companion, Worst Companion, One Dish

Before participants arrive

1. Draw or tape three columns on a shared wall or digital board labeled: 1. Best Companion, 2. Worst Companion, 3. One Dish.
2. Distribute three sticky notes and a pen to each participant.

Say this to open

We will take five minutes to answer three classic desert island questions. On separate notes, write who you would most want to be stranded with, who you would least want to be stranded with, and what single food dish you would bring. Fictional characters, public figures, or archetypes are welcome. Real colleagues are off-limits for the worst companion prompt. After writing, post them in the matching columns.

How to run it

1. Introduce prompts and ground rules 2 minutes

   Explain the three columns. Clarify the safety boundary: answers to 'Worst Companion' must be fictional characters, historical figures, or generic tropes, never teammates or present company. Participants may choose to sign their notes or keep them anonymous.

2. Silent writing 5 minutes

   Participants write one response per sticky note and post it under the corresponding column. Anyone choosing not to post an answer may submit a blank note or keep their paper.

3. Review columns together 6 minutes

   Read through responses column by column. For larger groups, read a representative sample of four to six notes per column to stay within time, inviting brief comments from authors if they want to claim them.

4. Wrap up and debrief 2 minutes

   Close the exercise with one or two light observations about common themes or surprising practical choices.

Debrief questions

• Which companion choice would give our group the highest practical survival rate?
• What common themes or food obsessions did you notice across our board?

Finished output: A three-column board displaying group responses to the three scenario prompts.

Remote

Use a three-column online whiteboard or shared document. Set a five-minute timer for typing cards. When time expires, share the screen and read through the columns aloud.

Hybrid

In-person participants write and post physical notes on a board next to an open camera, while remote participants type into an identical digital board or a shared chat. The facilitator alternates reading one physical note and one online note per column.

Access and participation choices

• Participants can submit anonymous notes or decline to write an answer for any of the three prompts without explanation.
• Responses can be submitted verbally, in written text, or via digital cards.

If the session gets stuck

Someone names a coworker or manager as the worst person to be stranded with.

Remind the room of the ground rule immediately, remove the note from public view, and refocus attention on fictional or archetypal examples.

Too many cards are posted to read every single one within six minutes.

Group similar responses quickly and read aloud three to five distinct or humorous cards per column instead of reading every card.

Terms used here

• Column review: Reading through posted notes categorized under a single topic heading before moving to the next.