Your team didn’t mess up. You didn’t ship a bug. You didn’t blow the budget. You didn’t miss a deadline. You just missed the wave. While others were pivoting, launching, or riding the momentum—you were still “prioritizing” or “waiting for clarity.” And it’s the most dangerous kind of failure: the kind no one notices until it’s too late. This calls not for a post-mortem, but a Lost Mortem.
The dramatic impact of retrospectives for continuous improvement should be clear to all by now. I’m going to assume your team’s doing regular post-mortems for failures. Hopefully, you practice pre-mortems for big initiatives. Yet these tend to focus on the execution of things on your roadmap. What about the things that never made it to the roadmap, but should have?
The Dog That Didn’t Bark
Sometimes, the absence of something is the biggest clue with got that there’s an underlying issue. When I see a company that continued on the wrong path for too long, I cannot help but wonder why no one spoke up sooner. These missed opportunities we’re looking for are the bigger, more meaningful kind. You’re not supposed to question and second guess every decision you’ve ever made. However, you should spot it when you missed something major.
After all, most startups don’t fail due to bad decisions—they die because of slow ones. When we’re complacent or vacillating, postponing a move till we’re forced to make it, momentum is lost. By the time you’re reacting, you’ve already lost the high ground.
Case Studies
To make it a bit clearer, here are some real examples. First, it’s the company that had everything needed to ride the LLM tiger first. They were doing genuine AI before everything exploded. They had internal talent that knew how to use GPT years ago. Yet when AI started changing their market completely, they were only starting to react, not taking the lead for months. This required a lost mortem to assess the company’s product strategy, executives’ performance, and culture that was holding their most innovative engineers from speaking up.
Another example is a startup that realized, months too late, that it has failed precisely in doing what it claims its product helps achieve. When dogfooding fails so embarrassingly, we have to take a long look at how we got there and debug the dissonance in the company’s culture.
Implementing Lost Mortems
Once a quarter, ask your leadership team:
“What game-changing opportunity should we have seen earlier?”
Don’t let this devolve into hindsight theater. Your goal isn’t to punish—it’s to build a radar. Who was in the best position to spot this and didn’t? What internal signals were ignored or deprioritized? What mental models, assumptions, or incentives led your org to stare straight at the future—and blink?
This isn’t about improving reaction speed. It’s about making your org allergic to stagnation. Ask questions to diagnose why something wasn’t seen on time. Did anyone know yet didn’t speak up? Did the company shoot down criticism? Did you wait for clarity instead of seeking it?
Cultural Red Flags
Lost Mortems expose the rot in your culture that retros and OKRs conveniently ignore. If any of these ring true, you’re not “focused”—you’re blind:
- Everyone’s scared to float “stupid” ideas.
- Your roadmap is a year-long concrete bunker.
- Pivot is a dirty word.
- Your best people stopped pushing for change because “it never goes anywhere.”
- Teams don’t challenge strategy—they “align.”
These aren’t quirks. They’re warning signs. They say you’ve built an organization optimized for inertia, not creating new momentum.
If you’re only doing post-mortems, you’re just congratulating yourself for stepping over the corpses. Lost mortems force you to ask harder questions: Why weren’t we first? Why didn’t we move sooner? Who saw it coming—and why didn’t we listen?
Every missed opportunity is a diagnostic moment.
You can either run a Lost Mortem now—or become one in someone else’s slide deck later.