A Path Less Taken
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A Path Less Taken

Retrospective Gamification: Retrospective from a Hat

Note: this retrospective technique introduces fun into retrospectives via gamification. For an example of another retrospective technique employing gamification, see Retrospective Gamification: Choose Five.


Before facilitating a retrospective from a hat, complete the following preparatory steps:

Come up with a list of at least five to ten things that could potentially be covered during a retrospective. By “things,” I mean any one of the following:

  • retrospective exercises (ideally any exercise you decide to include should be one the team has tried before, so you don’t have to provide a lengthy explanation of it if it is drawn from the “hat”). For examples of retrospective exercises, see the Retromat, and also my public Trello board, which provides a broad sample of retrospective techniques, some of which I designed, some from Retromat, and some from other sources).
  • topics (topics could include things like follow-up items from the last retrospective, or hot-button issues for that particular team)
  • questions (ideally from a question bank; see the sample question bank later in this post) Come up with a list of at least five to ten things that could potentially be covered during a retrospective.

Write the things on note cards or slips of paper

Make sure you have a container to put the note cards/slips of paper in (if you have an actual hat to use, great, but any container will do )


To facilitate the retrospective, do the following:

  • Describe what the “things” are that you have put in the hat (or other container)
  • Explain how many things are to be drawn from the hat, and how much time is to be spent on each thing (Depending on the size of the team and how much time you have set aside for the retrospective, it may not be possible for every team member to pick a thing during that session)
  • Invite one team member to pick a thing from the hat
  • Make sure everyone is clear on what the thing is and how long you will spend talking about the thing
  • Facilitate a conversation about the thing, using a white board or other media to capture key observations or outcomes
  • Use a smart phone stopwatch to alert the team on when it is almost time to move on to the next thing
  • Have another team member draw another thing from the hat, and facilitate a conversation about that thing (repeat this step until you run out of time or want to use a technique other than retrospective from a hat)
  • Use facilitation techniques such as powerful questions, affinity mapping, and dot voting to help the team converge on the outcomes most important to them, and what actions they might want to take as a result of the conversation

Question Bank

Below is a list of questions you can potentially choose from, along with the source where they originated, as applicable.

Some of my favorite questions/topics:

  • If we were to describe the Sprint that ended with one word, what would the word be?
  • What words of appreciation/thanks do we have for other team members?
  • The hardest technical challenges that we solved were …
  • The achievement we are most proud of is …
  • Open forum — what topics do we want to make sure we talk about today?
  • What do we think our goals might be for the next Sprint?

Ben Linders’ questions:

  • What did we do well, that if we don’t discuss we might forget?
  • What did we learn?
  • What should we do differently next time?
  • What still puzzles us?
  • What helps us to be successful as a team?
  • How did we do this sprint?
  • Where and when did it go wrong in this sprint?
  • What do we expect, from who?
  • Which tools or techniques proved to be useful? Which not?
  • What is our biggest impediment?
  • If we could change 1 thing, what would it be?
  • What caused the problems that we had in this sprint?
  • What’s keeping us awake at night?
  • Which things went smoothly in this sprint? Which didn’t?
  • Why did we do it like this?
  • Why did this (or didn’t this) work for us?
  • Why do we consider something to be important?
  • Why do we feel this way?
  • Why did we decide to work together on this?
  • What don’t we know yet?

David Mole’s Questions:

  • How do you feel overall about the project so far? (scale of 1–10)
  • If the project were a weather report, what would it be? (perhaps cloudy with a chance of a thunderstorm)
  • What is your confidence for completing the project/achieving the goals/intent? (scale of 1–10)
  • Our biggest constraint is …
  • One thing I want to discuss in this retrospective is …
  • One thing I am finding difficult is …
  • One thing I don’t understand is …
  • So far I have learned that …
  • If could change one thing right now it would be …
  • We would collaborate better if we …

Diana Larsen’s questions:

setting the stage

  • Ask “In a word or two, how are each of you doing today?”
  • Follow up with an outline of the retrospective goal and also a review of working agreements

gathering data

  • Probe for facts/significant events by asking questions like these: “As you think back over this iteration, what events or instances stand out? What did you see and hear that sticks in your memory?”
  • Next, check for responses to facts/events, by asking questions such as these: “How did your energy flow over the course of the iteration? When was it high or satisfying? When were the low points?”

generate insights

  • Based on the conversation up until now, ask “What would you recommend we keep doing the same, do more of, do less of, start doing, or stop doing altogether?”
  • Follow up by asking questions like: What are the implications of each if we do?” Looking at our keep, more, less, start, stop lists, which actions would have the greatest impact on our work or our teamwork?”

decide what to do

  • Keeping in mind the relative importance/impact of the various things that have been identified, ask: “Which of them do we have the most passion/energy to take as an action or experiment during the next iteration?”
  • Consider following that question up with: “What one or two will we select to include in our iteration planning meeting?”

close the retrospective

  • “Who owns each action item?” “How will we know when it’s complete?”
  • “What can we do to continue to improve our retrospectives? What should we keep doing, what should we try differently next time?”

Note: The inspiration for this retrospective approach was Bill Wake’s Tests from a Hat (which is a creative way to write unit tests, btw ; ). He in turn got the idea from Improv, where a technique called “Scenes from a Hat” is sometimes used.



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Philip Rogers

Philip Rogers

I’m an Agile practitioner at TextNow — I love to work with Agile teams to help them collaborate and deliver, and have fun while doing it.