#186: Why Teams Stop Caring About Retrospectives with Cort Sharp

#186: Why Teams Stop Caring About Retrospectives with Cort Sharp

May 27, 2026 · 33 min · Episode 13

About this episode

The episode discusses why retrospectives lose their value and how teams can make them more effective.

Retrospectives are supposed to help teams improve, but for many teams they slowly become rushed, repetitive, or skipped altogether. In this episode, Brian Milner and Cort Sharp unpack why retrospectives lose their value and what Scrum Masters and leaders can do to make them useful again. Overview When a team stops engaging in retrospectives, it is usually a symptom of something deeper. Sometimes the format has become stale. Sometimes the team no longer feels safe being honest. And sometimes the biggest issue is that retrospectives create plenty of discussion but very little meaningful change. In this conversation, Brian and Cort explore the most common reasons retrospectives begin to fail and how teams can rebuild trust in the process. They discuss the importance of psychological safety, why teams should focus on fewer actions instead of trying to fix everything at once, and how Scrum Masters can better tailor retrospectives to the personalities and working styles of their teams. They also share practical ideas for making retrospectives more engaging, more actionable, and more valuable over time. References and resources mentioned in the show: Cort SharpAmy Edmonson…

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