oldwinter Post-mortems & Retrospectives
Category: Leadership
Source: https://refoundai.com/lenny-skills/s/post-mortems-retrospectives
Post-mortems & Retrospectives | Refound AI
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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 entire company to uplevel other teams
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Carole Robin 1 quote
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"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?" Tactical: When a failure occurs, immediately ask: 'What is the lesson here?'Use the AFOG acronym to maintain perspective during painful setbacks.
View all skills from Carole Robin →
Christina Wodtke 1 quote
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"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." Tactical: Prioritize the 'why' behind the grade over the precision of the numerical score.Use the end-of-quarter retrospective to identify systemic blockers that prevented hitting 100%.
View all skills from Christina Wodtke →
Eeke de Milliano 2 quotes
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"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.'" Tactical: Rename 'post-mortems' to 'retrospectives'Shine a light on failure to mitigate the fear of taking big swings "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." Tactical: Encourage teams to send 'learning notes' about failed projects to the entire companyHave teams present failures and lessons learned at all-hands meetings
View all skills from Eeke de Milliano →
Janna Bastow 1 quote
Listen to episode →
"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? Okay, determine that something doesn't work. Are we allowed to go change it?'" Tactical: Use retrospectives to identify what is and isn't working and empower the team to change their situation
View all skills from Janna Bastow →
Maggie Crowley 1 quote
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"I remember... we decided we needed to do a rewrite, red flag number one... It didn't take six months, it took two and a half years... We skipped discovery. We didn't really write a one-pager, we just went for it." Tactical: Avoid 'side-by-side' rewrites of core productsNever skip discovery or requirements gathering for large technical projectsBe honest about 'sunk cost fallacy' when projects go off the rails
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Melissa Perri 1 quote
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"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." Tactical: Regularly audit your own 'toolbox' of frameworks and discard those that no longer serve your specific context.
View all skills from Melissa Perri →
Mike Krieger 1 quote
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"The confluence of those three things [mobile web deterioration, lack of viral spread, remote work]... we entered I guess 2024 and said, 'Look, there is a company to be built in the space. I'm not sure where the people would've built it. This concurrent incarnation we love, but it's not growing.'" Tactical: Evaluate if the ratio of input (effort) to output (growth) is fundamentally broken.Consider external factors like platform deterioration (e.g., mobile web) and internal factors like team distribution when assessing failure.
View all skills from Mike Krieger →
Ronny Kohavi 1 quote
Listen to episode →
"To me, a surprising experiment is one where the estimated result beforehand and the actual result differ by a lot. ... So 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." Tactical: Hold quarterly meetings specifically to review the most surprising experiment resultsAnalyze 'surprising losers' to uncover hidden factors like battery life impact or user friction
View all skills from Ronny Kohavi →
Shreyas Doshi 1 quote
Listen to episode →
"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." Tactical: Start with the prompt: 'Imagine this project has failed six months from now. What went wrong?'Categorize risks into 'Tigers' (lethal threats), 'Paper Tigers' (perceived threats), and 'Elephants' (unspoken issues).Include cross-functional members from engineering, sales, support, and marketing.
View all skills from Shreyas Doshi →
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