How to Organize a Great Team Retrospective

Retrospective help teams realize their impact and grow.

Last week we held a team retrospective for a massive 18 months project that we shipped to 1 Million merchants. Our team retrospective was a unique opportunity to reflect on the shared journey we experienced as well as revisit our processes, rituals, and tools. The main goal of the retrospective is to continue our team growth, and work better with each other. These changes will help us create more value faster.

Make sure the key contributors can attend

Ensure the key contributors can attend the event. This is especially important for long projects with many team changes. This activity’s main benefit is to create a shared context.

Be remote-friendly

If part of the team or the complete team is remote, use a virtual board tool like Miro, Google Draw, or Lucid Chart. Use the tool you regularly use to avoid technical glitches and delays.

Find a moderator who was not part of the project.

In an ideal world, the moderator should not be part of the project team. One of the goals of the moderator is to help the team self-reflect. A non-biased moderator will ensure everyone can express themselves and discern communication and trust issues more easily.

Ideally, the moderator should have some context on the project. This context can be gathered beforehand with some 1:1 interviews with individual contributors.

Scribe/Notetaker

Have someone responsible for taking notes. While you will have pictures or a virtual board with all the content, many exciting discussions will happen. The goal of the scribe is to capture the essence of these interactions.

Prepare a timeline

For long projects, prepare a timeline of the main events, including team member movements, role and scope changes (pivot?), significant decisions, major drawbacks, and key release dates. The timeline recreates an unbiased and shared bird’s eye view of the project. It will help everyone remember the challenges and, more generally, what happened during the project. Share it beforehand and bring a few written copies to the retrospective.

Timebox it

Block the required amount of time based on the project size and complexity. You should plan at least 20 minutes/question, up to 30 minutes. Err toward 30 minutes, especially for a large team project.

Here are some traditional questions:

• What went well?
• What went poorly / not so well?
• What actions will the team take to improve?

Be flexible: some questions may be more critical than others. Listen to the team and change the duration of the points to help go as deep as the teams feel comfortable doing.

Select a question and write post-its notes.

Some of us are introverts. Make sure you solicit everyone in writing before discussing any points. You can use physical and virtual post-its. For large teams, limit the number of post-its to 2–3 per person (for a 20-person team -> 40–60 post-its).

Clustering

Once you have everyone’s contribution, write down the virtual Post-it on a physical Post-it or use the virtual board.

The moderator will then cluster the various post-its into themes. Excellent opportunity for a short break ;-)

Each topic will be named based on the content of the multiple post-its, for instance, team trust, resource allocation, etc.

Use the number of post-its of each theme as a vote. Spend more time on the items with lots of Post-its. This way, you can respect the duration of each phase and still manage to discuss the most central theme. Because of the prioritization process and time-boxing, you may not have enough time to discuss some topics.

Talk

The moderator selects a theme (the one not yet discussed with the most post-its). He asks for contributions from the team: can someone explain and give more detail about this theme. A good discussion can occur: an example of what happened, more precision, and how the team member felt about it. Root cause analysis is a great principle: try to discriminate consequences from causes. Use the five whys technique to help the team reach a meaningful understanding.

The moderator will try to draw an agreed-upon conclusion from the team exchanges. At any point during the discussion, merging a theme with another one is possible. For instance, the link between the subject can also emerge as a causation link.

Change the question and repeat.

You can follow this process for these two questions

• What went well?
• What went poorly/not so well?

The third and last question What actions will the team take to improve? You can use the same technique (write on Post-it, cluster) if there is no strong consensus about what went poorly.

However, more often than not, problematic areas will emerge. The moderator can then help the group reach focus on these difficult areas. Her/his goal is to focus the team on what everybody agrees were the top problems and explore solutions and then decide on follow-up actions.

Conclusion

Use the meeting’s last 5–10 minutes to summarize the successes, significant issues, and improvement plan. Make sure you solicit everyone’s feedback.

Now is the time if you have a team ritual to end your meetings.

Our team ritual was to end our meetings with this one:

To shipping … and beyond.

Send a summary

Make sure all the participants receive an overview of the activity. The moderator and the notetaker will prepare this document. It will help everyone align and commit to the actions and changes discussed during the last phase of the activity.

One more thing

Of course, if the agreed-upon actions remain post-it notes on a physical or virtual board, the retrospective will not impact your team’s growth. Like any issue on the board, some team members must take ownership and change processes, rituals, and tools. The team has to be comfortable to unlearn certain things and learn new things.

In a way, the retrospective is only the beginning of a transformative process for the team. Do not confuse the retrospective with the team transformation.

Conclusion

Retrospectives are an essential agile ritual. Retrospectives offer quiet self-reflection time for the team. It can be super-powerful to:

• realize all the good things that the team has shared, learned and shipped;
• recognize the team’s culture, rituals, and values;
• carve-up changes that the team wants to pursue to improve to have more fun and deliver more value faster in the process.

Thanks

Thanks to Mike Grigoriev for the excellent Shipping Profile retro.

• How do you plan and organize your retrospective?
• Any advice to have better retrospectives?

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