Works with Claude, ChatGPT, Gemini, or your own local model: paste this prompt and your AI will co-facilitate this exercise with you.

Help me prepare and run the exercise below. First ask for my participant count, time, setting, access needs and intended result. Check these against the stated limits. Use the supplied rules and materials. Explain any proposed changes before using them, and label them as adaptations. Do not invent source claims or require personal disclosure. Give me one step at a time when I say start. I manage the people, physical activity and clock; do not claim to observe the room. Ask me what happened before choosing a next step.

Reference revision: ba90e8b49a7f35594be6bf93b41977581508a0fe9c3fb4711b1c0a704282b16f

# Cupid's Retrospective

Team members write reflection notes across four positive prompts covering personal efforts, team successes, future wishes, and peer appreciation. The group reads, clusters, and discusses the cards to agree on practical adjustments for the next cycle.

**Time:** 45 minutes. UWT suggested 45 minutes for a complete retrospective; source provided no explicit step durations.
**People:** 4 to 24. Individual silent reflection followed by whole-room silent reading, clustering, and facilitated discussion.

## Choose this exercise

**Purpose:** Surface individual contributions, positive project outcomes, forward-looking desires, and peer recognition to establish agreed improvement actions.
**Use it when:** At the close of a sprint, quarterly cycle, or project milestone when the team wants an appreciative reflection format before setting adjustments.
**Skip it when:** When a project experienced an active operational failure that requires immediate root-cause troubleshooting or critical incident analysis.

## Materials and tools

- 4 poster sheets or whiteboard sections labeled: Self-Love, Good Stuff!, Wishes for Tomorrow, and A Team to Die For
- 1 pad of sticky notes per participant
- 1 fine-tip marker per participant
- 1 countdown timer visible to the room
- Printed copies of the Cupid's Retrospective Prompt Guide (1 per participant, or 1 displayed as a reference poster)

## Before participants arrive

1. Draw four columns on a whiteboard or hang four poster sheets side by side.
2. Write the column headers clearly: Self-Love, Good Stuff!, Wishes for Tomorrow, and A Team to Die For.
3. Distribute one pad of sticky notes and one marker to each seat.
4. Place printed prompt guides on tables or post one prominently next to the board.

## Say this to open

Welcome. Today we are running Cupid's Retrospective to look back at our recent cycle through an appreciative lens. We will write notes across four areas: personal contributions, team successes, wishes for upcoming work, and coworker appreciation. You can write as many or as few notes as you want, and you choose how much detail to share.

## How to run it

### 1. Introduce prompts and framing (5 minutes)

Point to the four column headings and the distributed prompt guide. Briefly explain each category: Self-Love captures personal contributions; Good Stuff covers team achievements; Wishes for Tomorrow captures future workflow wishes; A Team to Die For contains direct appreciation for colleagues. Remind participants that all writing, posting, and sharing is optional.

### 2. Silent individual writing (10 minutes)

Start a 10-minute timer. Participants write in silence, placing one observation per sticky note. They can write across any mix of the four categories. When finished, participants walk to the wall and post their notes under the matching columns.

### 3. Silent reading and grouping (10 minutes)

Invite all participants to step up to the board and silently read the notes. Instruct everyone to cluster notes with related themes together within their respective columns, without altering or discarding anyone's cards.

### 4. Theme discussion and action capture (15 minutes)

Facilitate a walk through the four columns from left to right: roughly 2 minutes on Self-Love, 3 minutes on Good Stuff, 7 minutes on Wishes for Tomorrow, and 3 minutes on A Team to Die For. In the Wishes column, identify top themes and invite volunteers to define 1 to 3 trial commitments for the upcoming cycle. Write the agreed actions and owners on the board.

### 5. Debrief and close (5 minutes)

Pose the debrief questions to the room. Invite 2 or 3 brief reflections from volunteers, verify the recorded action items, and close the session on time.


## Debrief questions

- Looking at the Wishes column, which request would make the most practical difference in our next cycle?
- What shared strength showed up most consistently across the appreciations?

**Finished output:** A four-column reflection board containing grouped notes, peer appreciations, and 1 to 3 agreed action items with named owners for the next cycle.

## Remote

Set up a shared digital whiteboard with four labeled sections: Self-Love, Good Stuff, Wishes for Tomorrow, and A Team to Die For. Participants type their ideas on virtual sticky notes during the silent writing block, drag related notes into clusters during the reading block, and use digital raised-hand tools to offer comments during the discussion block.

## Hybrid

Use a single shared digital board for the entire group. In-person participants type their notes directly on their laptops, or write on physical notes that a volunteer in-room scribe enters into the digital board. Project the shared digital board on a large room display so both in-person and remote participants view the identical layout, clusters, and live edits simultaneously.

## Access and participation choices

- Participants may submit notes anonymously, skip any category, or choose not to write personal acknowledgments.
- Participants can contribute by writing physical notes, typing into the digital board, or observing quietly without an obligation to speak.

## If the session gets stuck

**Participants hesitate to write under 'Self-Love' out of modest discomfort.**

Provide a clear neutral example: 'I organized our shared folder structure after hours so newer members could find onboarding assets.' Emphasize that surfacing quiet work helps the whole team.

**Wishes are overly broad and do not translate to usable team steps.**

Select one prominent wish card and ask: 'What is one concrete task or experiment we can run in the next sprint to test this idea?'


## Terms used here

- Retrospective: A scheduled meeting where a team reflects on past work to agree on practical process improvements.

## Participant material: Cupid's Retrospective Prompt Guide

Cupid's Retrospective Prompts:

1. Self-Love
Tell us how you made a difference.
Example: I helped the marketing team understand our feature release schedule.

2. Good Stuff!
What did you like about the last cycle or project?
Example: Our sprint planning was concise and wrapped up on time.

3. My Wishes for Tomorrow
What are your wishes for the team's upcoming work?
Example: I would like to try pair programming on complex backend tasks.

4. A Team to Die For
Share appreciative words about your teammates.
Example: Rachel, thank you for your quick replies and patience during the server rollout.

## Sources and adaptation

Observed in EasyRetro template library; the site credits the template format to Neatro.

Retained the four core prompt categories, framing, and card examples from the Neatro template observed on EasyRetro. UWT structured the facilitation into a 45-minute retrospective sequence (introduction, silent writing, grouping, action discussion, and debrief), fixed material ratios to individual pads, added explicit hybrid scribe guidance, and defined clear debrief and access safeguards.

[EasyRetro](https://easyretro.io/templates/cupids-retrospective-template/)

Current run sheet: https://unitedwetransform.com/exercises/cupid-s/