Why We Keep Skipping Retrospectives (and How to Fix It)
Retrospectives. Lessons Learned. After-Action Reviews.
Different names, same idea—but here’s the thing: they’re often misunderstood.
Most people picture a single meeting at the end of a project where the team talks about what went well, what didn’t, and what to change next time. That’s part of it, but it’s not the whole picture.
At their best, these are ongoing cycles of conversation, feedback, and reflection—woven into the project from start to finish. The formal meeting is just a checkpoint. The real value comes from raising insights as they happen, discussing them in real time, and making small course corrections along the way.
The Problem: The Timing & Resourcing Trap
Here’s the common pattern:
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The project ends, and the team jumps straight into the next one.
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If a meeting happens, it’s weeks later, when people are busy, memories are fuzzy, and urgency is gone.
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Retros get cut first when budgets get tight, or if there’s no time or money set aside for them.
On the surface, it’s a scheduling problem. But dig deeper…
5 Whys: Getting to the Root Cause
1. Why don’t we hold retrospectives?
There’s no time after a project ends.
2. Why is there no time?
The team is already assigned to the next project.
3. Why are they assigned immediately?
There’s pressure to start new work to meet deadlines and revenue targets.
4. Why does new work take priority over reflection?
Learning is treated as “extra” instead of part of project delivery.
5. Why is it seen as extra?
it’s not built into the plan, the budget, or the culture—so it feels optional.
Root cause: Reflection isn’t embedded in the way the organization works. It’s an afterthought, not an essential.
Options for Fixing It
Bake It Into the Plan from Day One
Make reflection a deliverable, not an optional activity. Schedule it in the project timeline and budget for the time.
Use Milestone Moments
Hold short “pulse” retros at key points—design freeze, launch prep, major handover. Capture feedback while it’s fresh and act before it’s too late to change course.
Make Micro-Reflection a Habit
Spend 10 minutes in regular team meetings talking about how the team is working together, with the client, and to the project plan. Keep it light but consistent.
Capture As You Go
Use a shared space, chat thread, shared doc, retrospective tool, where anyone can log lessons in real time. This makes the end-of-project wrap-up faster and richer.
Connect It to Results
Track and share examples where lessons prevented repeated mistakes, saved time, or improved client relationships. Show the ROI of learning.
The Takeaway
If lessons learned feel like extra effort, they’ll always lose to “more urgent” work.
But if they’re continuous, planned, and built into the way you deliver projects, they stop feeling like an interruption, and start becoming the engine for improvement.
Because in the end, you don’t improve in the meeting—you improve in the work between meetings.
