post-mortems-and-retrospectives

What this skill does

# Post-mortems & Retrospectives

**Category:** Leadership

**Source:** https://refoundai.com/lenny-skills/s/post-mortems-retrospectives

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Post-mortems & Retrospectives | Refound AI

Lenny Skills Database     SKILLS  PLAYBOOKS  GUESTS  ABOUT               SKILLS  PLAYBOOKS  GUESTS  ABOUT                     Leadership   11 guests | 13 insights

Post-mortems & Retrospectives  Post-mortems and retrospectives are structured exercises for extracting learning from outcomes—both failures and successes. They matter because without intentional reflection, teams repeat mistakes, miss patterns, and lose the compounding benefit of institutional knowledge.

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The Guide  5 key steps synthesized from 11 experts.

1 Run pre-mortems to avoid ugly post-mortems  The best post-mortem is one you never have to run. Before launching a project, gather the team and ask: 'Imagine it's six months from now and this project has failed—what went wrong?' This hypothetical failure state creates psychological safety for people to voice concerns they'd otherwise withhold. Most importantly, use the pre-mortem to establish 'kill criteria'—specific signals that will trigger a pivot or shutdown.

Featured guest perspectives

"The idea is simple, which is when you are working on an important project or initiative, you get together with your team early on in the products or the projects' life to see in advance what could go wrong. And the way I describe a pre-mortem is that if you do a pre-mortem right, you will not have to do an ugly post-mortem."

— Shreyas Doshi    "What a pre-mortem allows you to do is to set up kill criteria. So kill criteria are just a set of signals that you might see that would tell you that it's time to pivot or stop because once we actually launch something, we're very, very slow to decide to quit."

— Annie Duke        2 Reframe failure as a learning opportunity  The language matters. Call it a 'retrospective' instead of a 'post-mortem' to emphasize learning over blame. When something goes wrong, the first question should always be 'What did we learn?' Adopt the AFOG mindset—Another F-ing Opportunity for Growth—to maintain perspective during painful setbacks and build long-term resilience.

Featured guest perspectives

"Instead of calling something a postmortem, call it a retrospective, so that it's a positive thing. Like, 'Hey, we're learning from this thing.'"

— Eeke de Milliano    "The acronym is A-F-O-G, another F-ing... Another Fucking Opportunity for Growth. Every student who ever took a class from me... knows that acronym because my question, when something has gone wrong or a person has experienced a failure, my first question is always, so what did you learn?"

— Carole Robin        3 Focus on the 'why' behind the numbers  Whether you hit 80% or 120% of a goal, the number itself is less valuable than understanding why. Use retrospectives to dig into systemic blockers, hidden assumptions, and unexpected factors. The same discipline applies to personal growth—regularly audit your own frameworks and discard those that no longer serve your context.

Featured guest perspectives

"What matters is, why 80%? Really focus on the learning... It's all about the retrospectives. Make sure your grading is secondary to retrospective, is the biggest thing I would say, because that's what's going to be valuable."

— Christina Wodtke    "I think the biggest message I can tell to anybody learning, is really, sit down, do a retrospective with yourself, and say, is this helping me get better at being a product manager? And if it's not, change it."

— Melissa Perri        4 Celebrate and share learnings publicly  Retrospectives build psychological safety when learnings are shared openly, not hidden. Have teams write 'learning notes' about failed projects and share them company-wide. Present failures and lessons at all-hands meetings alongside successes. This normalizes experimentation and reduces the fear of taking big swings.

Featured guest perspectives

"Have people talk about the failure in these sort of public forums, where usually you talk about the successes. So have someone actually write a note that's like, 'Hey, here are all my learnings from this thing that we did.' And send it to the org."

— Eeke de Milliano    "Retrospectives make such a big difference because they are indicative of psychological safety, which underpins so much, right? Once you start building in this psychological safety, the ability to ask questions and to start saying, 'What are we doing that's working? What are we doing that's not working?'"

— Janna Bastow        5 Prioritize surprising results over wins and losses  The most valuable retrospectives focus not on 'wins' or 'losses' but on surprises—outcomes where the delta between prediction and reality was largest. A 'surprising loser' that everyone expected to succeed often reveals hidden factors (battery drain, user friction, edge cases) that generate more organizational learning than a predictable success.

Featured guest perspectives

"To me, a surprising experiment is one where the estimated result beforehand and the actual result differ by a lot... we focused not just on the winners, but also surprising losers, things that people thought would be a no-brainer to run. And then for some reason, it was very negative. And sometimes, it's that negative that gives you insight."

— Ronny Kohavi    "The teams continuously document any learnings from data exploration, from experimentation, from user research and so on... Most of it is spent discussing learnings that have been documented, their implications, how they can be leveraged in follow up work."

— Ben Williams

✗ Common Mistakes

Skipping discovery and requirements gathering—failed projects often stem from rushing to build without understanding the problemTreating retrospectives as blame sessions rather than learning exercisesOnly reviewing failures—surprising successes also contain valuable lessonsNot setting kill criteria in advance, then falling into the sunk cost trap when projects go sideways     ✓ Signs You're Doing It Well

Your team comfortably shares failures in public forums without fear of punishmentYou have documented learnings from past experiments that inform current decisionsPre-mortems are a standard part of your project kickoff processThe ratio of input to output (effort vs. growth) is a regular topic of honest discussion

All Guest Perspectives

Deep dive into what all 11 guests shared about post-mortems & retrospectives.

Annie Duke 2 quotes

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"So a pre-mortem, it's great only if you set up kill criteria. Commit to actions that you're going to take if you see those signals."  Tactical:  Identify early signals that a project is failing during the pre-mortem.Pre-commit to specific actions (like killing the project) if those signals are met.    "What a pre-mortem allows you to do is to set up kill criteria. So kill criteria are just a set of signals that you might see that would tell you that it's time to pivot or stop because once we actually launch something, we're very, very slow to decide to quit."  Tactical:  Ask the team: 'Imagine it is six months from now and the project has failed. What were the early signals?'Create a list of 'kill criteria' based on these signals (e.g., inability to get a decision-maker in the room).

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Ben Williams 1 quote

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"We have these team level impact and learnings reviews... The teams continuously document any learnings from data exploration, from experimentation, from user research and so on. They document that in their weekly impact and learnings document... Most of it is spent discussing learnings that have been documented, their implications, how they can be leveraged in follow up work."  Tactical:  Hold weekly 'Impact and Learnings' reviews focused on insights rather than status updatesSocialize learnings across the ent