Purpose

The Proud and Sorry Retrospective is a simple, emotionally honest format where each team member shares something they are proud of and something they are sorry about from the sprint. It builds vulnerability and trust by normalizing both pride and regret, and it often surfaces personal accountability that other formats miss.

At a glance

• Group size: 3–10 people
• Duration: 15 minutes
• Difficulty: Beginner
• Facilitation style: Semi-structured
• Setting: Both / Remote-friendly

How to run

1. Explain the format: each person will share one Proud and one Sorry moment.
2. Silent reflection: participants think about their contributions (2 minutes).
3. Round-robin sharing: each person shares both (8 minutes).
4. Discuss patterns and common themes (3 minutes).
5. Optionally agree on 1–2 actions inspired by the Sorry items (2 minutes).

Materials needed

• Optional: sticky notes for written sharing
• Timer

Pitfalls & common mistakes

• Sorry becoming self-flagellation — frame it as a learning moment, not punishment.
• Only sharing trivial Sorry items to avoid vulnerability.
• Not balancing the discussion — both Proud and Sorry deserve equal weight.

Inclusion & accessibility

• Model vulnerability as the facilitator by sharing your own Proud and Sorry first.
• Respect that some cultures are uncomfortable with public expressions of pride or regret.
• Allow written sharing as an alternative to verbal.

Variations

• Proud, Sorry, Ask: add a third category for something you need help with.
• Team Proud, Team Sorry: focus on collective rather than individual items.
• Anonymous Proud and Sorry: submit anonymously, then discuss as a group.

When NOT to use this

• When trust is very low and Sorry items could be used against people.
• When the team needs a structural analysis rather than an emotional one.

Source & further reading

• Agile coaching community practices.
• Retromat (retromat.org).