Here are 29 thoughtful retrospective questions to help you consider past successes and failures so you can learn from them. Retrospective activities at the end of a sprint or when completing a new project are the optimal time to reflect on the goals and challenges faced and what was done to achieve and mitigate them. It can also help you identify any risks that may have surfaced along the way and develop strategies to avoid them in the future.

The retrospective ensures that everyone can share feedback without one or two people hijacking it. Team members use sticky notes (or a digital platform like google jam board when remote teammates are involved). Each member writes out what they like, and the group reads each statement aloud. This structure gives everyone an equal voice, even those who are more hesitant to speak up in a group.

Retrospectives allow you to identify emerging trends from team feedback. Then, develop tactical next steps to turn feedback into action for the next iteration. For leaders to encourage positive outcomes, they must share themes and the next steps immediately after the retrospective.

Plan a Retrospective in 5 Simple Steps

Team members need to feel comfortable giving honest feedback during retrospectives. Create a culture where constructive feedback is given and taken. All involved must be ready and willing to hear the truth without taking anything personally. Here are 5 simple steps to set the stage for a team retrospective:

Step 1 - Pick a Subject 

Choose a Project, Team, or Subject for Review Retrospective activities at the end of a sprint or when completing a new project are s a great time to reflect on the goals and challenges you faced and what you did to achieve them.

Step 2 - Set an Objective 

Set an Objective Define your primary purpose for a retrospective. For example

• I want to reduce risk in my project.

• I want to improve my team's dynamic. 

• I want to create new ways of communicating pain points.

Check out our free meeting objective template.

Step 3 - Set an Agenda

Set an Agenda An agenda articulates to attendees that you will run an orderly workshop and that productivity is the objective. An agenda in your invitation allows the participants to prepare. A well-thought-out agenda allows you to plan your speaking notes and ensure that one subject does not monopolize your entire workshop. The more prepared participants feel, the more likely they will engage during the workshop.

Step 4: Identify your attendees. 

If you are unsure whom you want to attend, use our Stakeholder Mapping Engagement Planner to find your most influential and impactful workshop participants.

Open To Everyone: Ideal for a meeting to give your team a chance to learn something new or share their experiences. 

Limited Group: Ideal for a meeting focused on improving team connections and communication.

Step 5 - Send a Meeting Invite

A business meeting invitation should include all the information an individual needs, such as the agenda, objective, date, time, location, and, most importantly, the value to the participant. Remember to keep it short and to the point.

Recommended Retrospective Agenda

• WELCOME - 10 mins

  • Team intros & context

• ICEBREAKERS - 15 mins

  • Build energy and focus

• RETROSPECTIVE - 40 mins

  • Retrospective Workshop

• CLOSING - 5 mins

  • Discuss next steps

29 Retrospective Questions

1. What did we do well that, if we discuss, we might remember?

2. What did we learn? 

3. What should we do differently next time? 

4. What still puzzles us? 

5. What are you most proud of? 

6. What value did you create? 

7. Who was your 'older sibling' during the last sprint? 

8. How can we unify as a team better in the upcoming sprint? 

9. How would this add to the experience? 

10. What could you add to improve? 

11. What is missing? 

12. What is keeping you up at night? 

13. What support do you need? 

14. If you were Batman, who on the team would be your Robin?

15. How can you be of use to help the team in the upcoming XXXX? 

16. What advice would you give your younger self? 

17. How well did we hit our action items? 

18. Which tools or techniques proved to be helpful? Which not? 

19. Why do you consider something important? 

20. Who made this XXXXX better or more manageable for you? 

21. What can we be proud of as a team? 

22. Did you ever feel like things took a wrong turn? If so, why? 

23. How would you deal with [X issue] in hindsight?

24. What can we do to replicate the successful parts of this XXXX? 

25. What's still puzzling or unresolved about our process or an issue? 

26. What's the smallest thing you could do to improve? 

27. What is the outcome you're looking for? 

28. What help do you need to make this action item happen? 

29. What would a successful solution look and feel like?

Retrospective Strategic Planner

Run Effective Retrospectives, Strategic Planner with 6 Engaging Team-Building Activities. Discover team health-check resources and step-by-step facilitation guides for interactive and productive collaboration. These workshop & meeting templates are perfect for project managers and anyone who runs a team of lead products.

Outcomes of Retrospective meetings:
✔️ Promote transparency and accountability to teammates.
✔️ Create better features by focusing on user needs.
✔️ Improve collaboration among team members.
✔️ Reduce risk by fixing problems before they escalate.

What do you think of our 29 thoughtful retrospective questions? Tell us your favourite retrospective questions.