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50+ Retrospective Questions for your Next Meeting

photo of two people at a table, one with a laptop

Retrospectives should be easy in theory. Just ask a few questions – What went well? What didn’t go well? What did we learn? – and sit back and watch as the learning happens.

Anyone who has ever run a retrospective can tell you that’s not how it goes. People may feel afraid of looking foolish in front of colleagues or may not want to be the first one to speak up.

The hallmark of a great agile retrospective facilitator – whether that’s your Scrum Master, Agile Coach development team member – is being able to ask the right questions to provoke meaningful responses and trigger learnings.

This resource offers up a menu of powerful questions you can ask in your next sprint retrospective to take your conversations to the next level.

We’ve grouped questions according to purpose:

What makes a great retrospective question?

The facilitator’s role is not to answer the team’s questions and find solutions. That’s the development team’s job. The facilitator should ask questions that can provoke deeper thinking and illuminate the path towards continuous improvement.

A great facilitator retrospective question has the following characteristics:

1. Invites input from all participants

Every team member brings a unique perspective and experience, and it’s critical to involve everyone so that you get a full picture of what happened during your last sprint. The best questions attract input from the whole team, rather than just a few dominant voices.

Make sure you don’t move on from a question after only hearing from one person. Try to get others contributing as well. One way to do this is to ask follow-up questions like, “Who else wants to share their thoughts on this?” and making sure that everyone who has something to say on the question has their chance to be heard.

2. Is open-ended to encourage deeper reflection

Questions that steer participants toward one particular answer aren’t helpful. Facilitators serve the team so should position themselves as knowledge seekers without bias. Overly biased or anchored questions can encourage black-and-white thinking rather than inviting reflection and exploration. 

Try asking open-ended questions that can have multiple, equally valid answers. These questions welcome a diverse set of ideas and perspectives. They spark healthy conversations, inspire new ideas, and build a stronger sense of psychological safety in agile teams.

For example, rather than asking a leading question like, “Did you have too much on your plate during this sprint?” you can ask a more open-ended question such as, “How do you feel about the scope of work that we tried to accomplish during this sprint?”

The first question limits the range of answers you’ll get (“Yes” or “No”), which limits the opportunity for learning. The second one invites a wide variety of answers that may include nuances like, “It felt OK at the start, but then this roadblock happened, and it really backed things up.”

3. Gets teams to take ownership of the discussion

When facilitating a retrospective, you want to nurture the discourse, not dominate it. Good questions encourage team ownership of their work, which is a recurring theme in various Agile frameworks. Rather than sitting back and waiting for authority figures to provide answers, good questions encourage teams to respond by taking charge of the discussion, exploring the question and its possible answers without looking upwards to an authority figure for answers.

4. Avoids embarrassing team members

A question that embarrasses any team member or generates answers that embarrass or blame other team members can cause teammates to stay quiet in future retrospectives and damage psychological safety. Good questions steer clear of putting individuals or teams on the defensive.

For example, rather than asking a personnel-oriented question such as “What could the ops team have done better?”, ask questions that center on systems and processes, such as “Did any processes or systems create problems for you during this sprint?”. Not only does this help you avoid creating shame in your team members, but it also helps you build better systems and processes.

50+ retrospective questions to get teams talking

Most sprint retrospectives involve answering questions that are built into popular retrospective templates such as Start Stop ContinueWhat Went Well?4Ls, and many others.

The questions in this resource are intended to help facilitators who need to probe further after your agile team has done their initial reflection on the sprint. 

Retrospective check-in questions

Getting everyone to contribute to the retrospective is essential to having a productive conversation that gives you the most useful and actionable information possible. Ease into the retrospective with icebreaker-style questions that create psychological safety and get everyone comfortable contributing to the discussion.

(Time permitting, get as many team members as you can to answer each question.)

  1. Let’s start with some shout-outs. Who helped you out on this sprint? 
  2. Who made this sprint better or easier for you? (Be ready to go first to get the ball rolling.)
  3. What’s something you admire about a colleague’s work this sprint?
  4. On a scale of 1–10, how do you feel this sprint went? (Follow up by asking, “Why?”)
  5. What’s one word would you use to describe this sprint?

What went well questions

It’s easy, even natural, for a retrospective to focus on what went wrong. After all, the goal is to fine-tune processes and adjust the team’s behavior. But it’s important to focus on what went right, too, and even in the most challenging sprints, good things happen.

Set the tone for a positive discussion by taking time to highlight the positives:

  1. Did anything about this sprint go better than you expected it to? If so, what?
  2. Did anything go better during this sprint than during the previous one? If so, what?
  3. What tools, techniques, and/or resources helped you during this sprint?
  4. Did any of the improvements from our previous retrospective help you this sprint?
  5. If our team were a superhero, what were its superpowers this sprint?
  6. What can we be proud of as a team this sprint?
  7. What did you learn this sprint? 

What didn’t go well questions

Asking “what could have gone better?” can be useful. But to really dig deep, you need to ask more probing, specific questions. To get to the root causes of any issues that may have kept your team from doing their best work, try these questions at your next retrospective:

  1. During this sprint, did you ever feel like things took a wrong turn? If so, what happened?
  2. What about this sprint was the biggest source of stress or difficulty for you personally?
  3. Did anything happen during this sprint that caught you off-guard? 
  4. How did you cope with things that went wrong?
  5. How could you have coped better?
  6. What do you think contributed to (thing that didn’t go well) happening?
  7. How did (thing that didn’t go well) impact your ability to do your best work?
  8. What resources do you wish you’d had (or had more of) during this sprint? How would they have made a difference?
  9. What’s our weakest link as a team?
  10. How would you deal with [X issue] in hindsight?
  11. Did any processes or systems create problems for you during this sprint? If so, how?

Future-oriented retro questions

A good sprint retrospective meeting generates knowledge and ideas that lead to changes in how the team performs the next sprint. Some of these will come out naturally during the discussions that the previous questions create, but you can also use the questions below to focus the team’s attention on what they’ve learned and what they think should change for the next sprint.

  1. If you could go back and change one thing about this sprint, what would it be?
  2. If you could go back in time and do this sprint over, what would you NOT want to change? 
  3. What worked perfectly this sprint?
  4. What surprised you this sprint?
  5. How can we build on what went well during this sprint?
  6. What did you learn during this sprint that will make the next one better or easier for you?
  7. What can we do to replicate the successful parts of this sprint?
  8. What can you do that will make the sprint go better for your fellow team members?
  9. What would a successful next sprint look like?
  10. What do you definitely NOT want to see in the next sprint? 
  11. What changes could we make to support our future vision? What else might be affected by those changes? Are there any trade-offs we need to make?
  12. How can we improve the overall process(es) that we used during this sprint?
  13. What’s still puzzling or unresolved about our process or an issue?

Retrospective action item questions

Sometimes getting a team to answer what went well or didn’t go well is the easy bit. The hard thing is converting learnings into action items to forward for your next iteration. Effective retrospectives crystallize learnings into concrete next steps because continuous improvement only happens when action is taken on your retrospective ideas. 

Here are some of our favorite retro questions for generating next steps:

  1. What’s the smallest thing you could do to make an improvement to [X issue]? 
  2. What’s the cost of doing nothing about [X issue]?  
  3. What would you do if you were 100% responsible for this issue?
  4. Of the action items we’ve identified, which one will have the greatest impact?
  5. What would an experiment look like to improve this issue? 
  6. What is the outcome you’re looking for?
  7. What would a successful solution look and feel like?
  8. What help do you need to make this action item happen?
  9. Why? (Using a structured questioning approach like Five Whys can help you get to the root cause of any process issue and help with brainstorming action items)

Team wellbeing questions

Effective sprint retrospective meetings don’t just debug process issues, they also focus on the humans that form up the team. After all, the Agile Manifesto talks about people over processes and tools. Taking time to discuss team wellbeing, identifying issues, and finding improvements, is just as important as it is for your working processes.

  1. What’s keeping you up at night about our work as a team, if anything?
  2. What’s one thing that, if taken off your plate, would improve the quality of your work?
  3. How do you feel about your work/life balance this sprint?
  4. If you could have additional support on one thing, what would it be?
  5. Are there aspects of our team culture that can be improved?
  6. Do you feel over-worked, under-worked, or that you have just the right workload?
  7. What do you feel motivated by right now?
  8. On a scale of 1-10, how energized do you feel going into the next sprint?

Better questions = better retrospectives

Facilitators are more than just a meeting’s stage-manager. Like a therapist, their role is to ask questions that help the team discover learnings themselves. Those learning may be about behaviors, processes, or even ways of thinking about an issue. 

A facilitator’s greatest tool is a well-asked question that helps teams get to the core of an issue. In this article we’ve expanded your toolbox with 50+ questions to help you serve your teams better and deliver enlightenment as a facilitator. 

Now it’s time to try them out with your team. 

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