Today someone wrote with an inquiry, "What kinds of questions should one ask when doing a retrospective? What specific areas should a leader think about when drafting a retrospective, regardless of the rest of the format?"

I found this a difficult question to answer, yet I resisted writing back, "It depends." Though it does depend, on a number of factors, but most of all the goal. So, here's what I wrote back to him.

In Agile Retrospectives, Esther and I recommend setting a goal for each retrospective, then tailoring the activities and questions to that goal. Many teams have an ongoing goal of "continuous product improvement" or "continuous process improvement" but it's also good to switch things up occasionally so your retrospectives don't get stale. Teams have retrospected on goals including, "a closer look at our interactions with customers," "how well are we following our agile values or practices?" or "what's going on with the build?", and many others. The goal does depend. It depends on the experience of the iteration and the need for a more general or more specific review. Once you have a goal, the questions come more easily.

Questions should lead the group through the group thinking framework of the retrospective. For example, for a continuous improvement goal:

  1. setting the stage: "In a word or two, how are each of you doing today?", then outline goal and review working agreements;
  2. gathering data: Look for facts/events, "As you think back over this iteration, what events or instances stand out? What did you see and hear that sticks in your memory?" and when the group has answered those questions, move on to looking for responses to the facts/events, "How did your energy flow over the course of the iteration? When was it high or satisfying? When were the low points?";
  3. generate insights: "Now that we have a full picture of what happened and how we responded, what would you recommend we keep doing the same, do more of, do less of, start doing, or stop doing altogether?" and "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?" ;
  4. decide what to do: "Considering the impact of each of the items on our list, which of them do we have the most passion/energy to take as an action or experiment during the next iteration?" "What one or two will we select to include in our iteration planning meeting?" (A recent conversation with Esther brings the last two questions to mind. We actually talk about this stuff in our spare time too. ;-) )
  5. 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?"

It's hard to say what specific questions to ask; however, I use the book "The Art of Focused Conversation" edited by R, Brian Stanfield, as a source of ideas for questions that fit the retrospective framework, the goal, and the context of the team.

Of course, this is only one among many ways to ask questions during a retrospective. Keep practicing until you find the best fit for you.