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100 Questions to Ask During a Team Retrospective

August 18, 2026

100 Questions to Ask During a Team Retrospective

No. Item Definition
1. How did we celebrate wins? Ask about celebrating success.
2. How did we handle change? Ask about change response.
3. How did we handle pressure? Ask about pressure response.
4. How did we make decisions? Ask about decision-making.
5. How did we resolve issues? Ask about issue resolution.
6. How did we support each other? Ask about mutual support.
7. How did we use feedback? Ask about feedback use.
8. What assumptions were wrong? Ask about faulty assumptions.
9. What blocked our progress? Ask about obstacles faced.
10. What boosted morale? Ask about morale gains.
11. What bottlenecks emerged? Ask about workflow bottlenecks.
12. What caused rework? Ask about repeated effort.
13. What changes caused churn? Ask about disruptive changes.
14. What changes created value? Ask about valuable changes.
15. What commitments held? Ask about kept commitments.
16. What commitments slipped? Ask about delayed commitments.
17. What communication failed? Ask about poor communication.
18. What communication worked best? Ask about effective communication.
19. What concerns went unspoken? Ask about unspoken concerns.
20. What created confusion? Ask about confusion sources.
21. What data did we lack? Ask about missing information.
22. What data helped decisions? Ask about useful information.
23. What decisions came too late? Ask about delayed decisions.
24. What decisions worked well? Ask about good decisions.
25. What delivered customer value? Ask about customer benefit.
26. What dependencies hurt us? Ask about harmful dependencies.
27. What did customers notice? Ask about customer observations.
28. What did stakeholders praise? Ask about positive stakeholder feedback.
29. What did stakeholders question? Ask about stakeholder concerns.
30. What did we learn? Ask about lessons gained.
31. What didn’t go well? Ask about problems and setbacks.
32. What drained our energy? Ask about energy loss.
33. What escalations happened? Ask about escalations.
34. What estimates were accurate? Ask about accurate estimates.
35. What estimates were off? Ask about inaccurate estimates.
36. What expectations were clear? Ask about clear expectations.
37. What expectations were missed? Ask about unmet expectations.
38. What experiments failed fast? Ask about quick failed tests.
39. What experiments paid off? Ask about successful experiments.
40. What feedback came too late? Ask about delayed feedback.
41. What feedback was timely? Ask about prompt feedback.
42. What felt frustrating? Ask about frustrations.
43. What felt most valuable? Ask about highest value.
44. What felt rushed? Ask about rushing.
45. What felt stressful? Ask about stressors.
46. What felt sustainable? Ask about sustainability.
47. What goals did we meet? Ask about achieved goals.
48. What goals did we miss? Ask about missed goals.
49. What habits helped the team? Ask about helpful habits.
50. What habits hurt the team? Ask about harmful habits.
51. What handoffs were messy? Ask about poor handoffs.
52. What handoffs were smooth? Ask about smooth transitions.
53. What helped us focus? Ask about focus aids.
54. What helped us succeed? Ask about enabling factors.
55. What hurt collaboration? Ask about teamwork issues.
56. What improved collaboration? Ask about teamwork gains.
57. What incidents affected us? Ask about incidents.
58. What interrupted our flow? Ask about flow disruptions.
59. What lowered morale? Ask about morale drops.
60. What made focus difficult? Ask about distractions.
61. What made work enjoyable? Ask about positive experience.
62. What meetings wasted time? Ask about unhelpful meetings.
63. What meetings were useful? Ask about valuable meetings.
64. What missed customer needs? Ask about unmet needs.
65. What ownership was unclear? Ask about unclear responsibility.
66. What ownership worked well? Ask about clear responsibility.
67. What planning failed us? Ask about poor planning.
68. What planning worked well? Ask about effective planning.
69. What priorities were unclear? Ask about unclear priorities.
70. What process step broke down? Ask about process failures.
71. What quality issues appeared? Ask about quality problems.
72. What quality practices helped? Ask about useful quality practices.
73. What recoveries went well? Ask about good recoveries.
74. What recoveries were slow? Ask about slow recoveries.
75. What risks did we miss? Ask about overlooked risks.
76. What routine should change? Ask about changing routine.
77. What should we improve? Ask for improvement ideas.
78. What should we keep doing? Ask what to continue.
79. What should we start doing? Ask what to begin.
80. What should we stop doing? Ask what to discontinue.
81. What slowed us down? Ask about delays.
82. What sped us up? Ask about accelerators.
83. What standards improved? Ask about better standards.
84. What standards slipped? Ask about lowered standards.
85. What support did we get? Ask about received support.
86. What support did we need? Ask about needed support.
87. What surprised us? Ask about unexpected events.
88. What tensions surfaced? Ask about tensions.
89. What tools got in the way? Ask about obstructive tools.
90. What tools worked well? Ask about effective tools.
91. What voices were missing? Ask about missing input.
92. What was harder than expected? Ask about unexpected difficulty.
93. What was least effective? Ask about poor effectiveness.
94. What was most effective? Ask about effectiveness.
95. What was unclear? Ask about confusion.
96. What went well this sprint? Ask about successes and positives.
97. What work had low impact? Ask about low value.
98. What work had most impact? Ask about highest impact.
99. Where did we gain momentum? Ask about productive moments.
100. Where did we lose time? Ask about inefficiencies.
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