Project Failure Files: Not Learning From Mistakes

In Episode 69 of the Project Failure Files weekly webcast, our focus was “Relying on Memory Alone,” in which Sharon and I take aim at a quiet productivity killer: trusting memory to carry lessons from one project to the next. We unpack how “we’ll document it later” turns into never, especially when projects overlap and attention shifts to the next deadline. The result is Groundhog Day delivery—teams re-fight the same fires, and organizational intelligence walks out the door whenever a key person leaves.

We argue for institutionalizing learning: short milestone debriefs, simple shared workspaces, and a standing post-mortem that feeds a searchable repository. Documentation isn’t busywork; it’s part of the deliverable. Rewarding contributions and making knowledge easy to find turns capture from a chore into a cultural reflex.

Finally, we draw a line between tech debt and “knowledge debt.” AI (Copilot, meeting notes, transcripts) can reveal patterns across projects—but only if the data exists. Start recording now, standardize the review loop, and measure improvement against a living playbook. That’s how teams move from chaos-on-repeat to compounding gains.

Enjoy the episode!

Be sure to tune in next Monday, December 15th at 9am Pacific for a program update on our weekly series. Hope you can join us on our NEW YouTube channel (please subscribe!), or find us on LinkedIn.