Proud and Sorry

Choose this exercise

Purpose: Review project successes and setbacks together to agree on practical changes for the next effort.

Use it when: Use at the conclusion of an initiative or during a project kickoff when team members share prior working history.

Skip it when: Skip with brand-new teams who have no shared history, or in high-conflict teams lacking basic conversational safety.

Group arrangement: Individual reflection followed by stable small groups of 3 to 5 people.

Timing: 15 minutes matches the maximum duration from the Relationship Makers Handbook source record.

Materials and tools

• One index card or blank sheet of paper per person
• One pen or pencil per person
• One countdown timer visible to the room
• A board or slide displaying the two reflection prompts
• For remote or hybrid delivery: a video meeting with breakout rooms and shared chat for agreed group adjustments; personal reflections stay in private notes
• For hybrid delivery: one internet-connected device and headset per participant, with separate speaking positions for everyone in the room

Before participants arrive

1. Arrange seating into small tables or clusters of 3 to 5 participants who worked on the target project.
2. Write the two prompts visibly on a board or slide: 1. Proud of... 2. Disappointed or sorry about...
3. For hybrid delivery, test individual devices, headsets, breakout access and separated speaking positions before starting. If this equipment or space is unavailable, run fully in person or fully remotely.
4. Plan groups from the full participant roster, regardless of location. For 4 or 5 people, use one group. For larger totals, use as few groups as possible with at most 5 each, distributing people evenly; every group will contain 3 to 5 people.

Say this to open

We are taking 15 minutes to reflect on our recent shared work. You will write down one thing you are proud of from the project, and one thing you are sorry about or disappointed by. Then we will share in small groups and extract one lesson to take forward. You decide what level of detail you want to share.

How to run it

1. Introduce and write individually 3 minutes

   State the opening script. Direct everyone to take an index card and draw a line down the middle. On the left, write one specific project outcome or action you feel proud of. On the right, write one disappointment, misstep, or missed opportunity you feel sorry about. Writing is silent.

2. Share in small groups 6 minutes

   In groups of 3 to 5, each person takes up to 60 seconds to read or describe their two items without debate. Group members listen without interrupting or defending. If a participant prefers to pass, they may simply say pass and listen.

3. Analyze root patterns and forward actions 4 minutes

   Groups spend four minutes discussing the underlying patterns: what conditions helped the proud moments happen, and what caused the disappointments? Each group agrees on one specific habit or operational adjustment they want to carry into their next project.

4. Harvest key takeaways 2 minutes

   Ask two or three groups to share just their forward adjustment with the wider room. Collect or photo-document group note cards if teams want them recorded.

Debrief questions

• What common patterns appeared across the things we were proud of?
• What shared condition contributed to the items we felt sorry about?
• What is one concrete agreement we will carry into our next phase?

Finished output: A list of individual reflections and at least one concrete forward adjustment per small group.

Remote

Run in an online meeting platform. Provide an individual digital notepad or private text editor for the 3-minute silent reflection. Move participants into breakout rooms of 3 to 5 for the 10-minute sharing and analysis steps. Have one spokesperson per breakout paste their team's single forward adjustment into the main chat upon returning.

Hybrid

Everyone joins the same video call on an individual device and headset. Seat room participants apart and mute except when speaking. Form breakout groups of 3 to 5 from the full roster, regardless of location. Keep the same 3-minute private reflection, 6-minute sharing with 60-second turns, 4-minute group analysis and 2-minute harvest. Each group posts only its agreed forward adjustment in shared chat; invite two or three groups to speak. Private notes stay unshared unless their author chooses otherwise. If individual equipment or separated speaking space is unavailable, run fully in person or fully remotely.

Access and participation choices

• Participants may choose whether their reflection focuses on personal contributions or collective project results.
• Any participant may pass during the sharing round by stating pass, with no reason required.

If the session gets stuck

A participant uses the sorry prompt to openly blame a colleague.

Intervene immediately and remind the group: Keep the sorry item focused on your own actions, shared project conditions, or systemic roadblocks, rather than personal finger-pointing.

One person talks for the entire small group sharing window.

Enforce the 60-second limit per person by calling out time transitions from the main facilitator position.

Terms used here

• Proud and Sorry: A retrospective framework contrasting positive achievements with honest acknowledgments of shortcomings.