A love letter to retrospectives (+tips)
3 min read

A love letter to retrospectives (+tips)

To quote my favorite book on retrospectives (yes, I have a favorite book on retrospectives), a retrospective is "a special meeting where the team gathers after completing an increment of work to inspect and adapt their methods and teamwork." Retrospectives can apply to all sizes and shapes of work, for all teams and they should be conducted for ~every workstream.

Retrospectives are so effective because they help the whole team learn together, and then use those learnings to create change. They focus not only on the work itself, but also, critically, on team dynamics. They help emphasize and implement methods of work and qualities of teams you want to continue, and come up with a plan for those that you want to change. Retrospectives are *not* a punishment for work that went sideways. They are just as valuable for work that has gone exceedingly well. They are all about what you want to take with you into the future.

As a bonus, when done well, the very act of participating in a retrospective can also bond teams and build trust through dispassionately aligning on an account of events, facilitating open-minded discussion, and a collaborating on a vision for the future.

Here are best practices for conducting retrospectives

First, a note on language

The term “retrospective” is often interchanged with “post-mortem.” I advise you insist upon using the term “retrospective.” The primary definition of post-mortem is “an examination of a dead body to determine the cause of death.” The term is morbid and connotes death which does not align with the goal of the retrospective which is to promote health in the work.

When to retrospective

There should be some space between the completion of the work and the retrospective. The magnitude of that space will be determined by the length and complexity of the project as well as the level of controversy. The longer, more complex, and more contentious, the longer you should take. However, it shouldn’t be so much space that team members start forgetting details. The max you want to wait is about a month.

You can do a retro on your own, or get a group together for a discussion.

Who to invite

Everyone at the retrospective is expected to participate in discussion, help make decisions, and be a part of the next steps. As such, attendees should include those closely related to the work. Participants should not be restricted by team or function.

For more substantiative retrospectives, it may be helpful to have someone in the room that is not close to the work. This person can focus on the process and structure of the retrospective and remain neutral in the discussion.

The better the discussion, the more effective the retrospective. The two highest contributing factors to the quality of discussion are 1/ how prepared attendees are and 2/ how well the retrospective activity goes. Both require planning.

Preparing (yourself and others) for the retrospective

There are many different flavors of retros (I like ‘Stop, Start, Continue’, template here) and often they require materials (ex- sticky notes, poster paper, colored pens or your favorite collaboration tool du jour–Figma, Miro, etc.). Make sure you’ll have these on time for the retrospective. (I’d also recommend making a list of topics, themes, or events that you hope come up. This way, if they don’t, you can seed conversation.) Once you know your activity, send a heads up to the team with some details of the activity so that they can prepare their thoughts.

Your prep note might include the following details:

  • A reminder of what a retrospective is and why it’s a good practice to do it
  • A proposed goal for the retrospective
  • Most likely, it should be something related to developing learnings that can be leveraged in the future (either by your particular team, or your organization more broadly)
  • When you will be meeting
  • Who else will be attending
  • A proposed scope for discussion
  • A description of the activity
  • And a request that attendees prepare thoughts in advance to be shared during the activity
  • An invitation for questions or input in advance of getting together

The recap

The retrospective artifact is critical for maximizing the impact of a retrospective because this is the thing you're going to send around for anyone to learn from. Tell the story. Make it compelling. (And, easily scannable).

Your recap note might include the following details.

  • Key learnings
  • What you'd do differently next time
  • Decisions
  • Next immediate steps (with owners)
  • Ideas other's doing similar work might want to keep in mind
  • Your personal editorial

If you’re looking for more

Or think retrospectives could be your bag, I highly recommend reading Agile retrospectives: making good teams great. It goes really deep on not only the practices, but also the principles behind them. It also suggests ~a dozen excellent activities. If you do read this book, you’ll see that I borrowed many of the ideas for this chapter.