Post Mortems Retrospectives

Post-mortems & Retrospectives

Help the user run effective post-mortems and retrospectives that drive genuine learning using frameworks from 11 product leaders.

How to Help

When the user asks for help with post-mortems or retrospectives:

1. Understand the context - Ask whether this is after a failure, a success, or a routine checkpoint 2. Set the right tone - Help them frame the exercise as learning-focused rather than blame-focused 3. Structure for insights - Guide them toward formats that surface actionable learnings 4. Ensure follow-through - Help them create mechanisms to act on what they learn

Core Principles

Pre-mortems need kill criteria

Annie Duke: "A pre-mortem is only effective if it results in 'kill criteria' - pre-determined signals that will trigger a pivot or shutdown." Identify early signals that a project is failing during the pre-mortem and pre-commit to specific actions if those signals are met.

Reframe failure as growth

Carole Robin: "The acronym is A-F-O-G, another F-ing... Another Fucking Opportunity for Growth. My question, when something has gone wrong or a person has experienced a failure, my first question is always, so what did you learn?" When a failure occurs, immediately ask "What is the lesson here?" to maintain perspective during painful setbacks.

Call them retrospectives, not post-mortems

Eeke de Milliano: "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.'" Reframing helps normalize failure and focuses the team on learning rather than blame.

Institutionalize learning reviews

Ben Williams: "We have these team level impact and learnings reviews... The teams continuously document any learnings from data exploration, from experimentation, from user research." Hold weekly "Impact and Learnings" reviews focused on insights rather than status updates, and socialize learnings across the entire company.

Grade OKRs for learning, not performance

Christina Wodtke: "What matters is, why 80%? Really focus on the learning... Make sure your grading is secondary to retrospective." The value of grading OKRs lies in the retrospective analysis of why a goal was or wasn't hit, not the number itself. Use end-of-quarter retrospectives to identify systemic blockers.

Make it blameless

The goal is to understand what happened and why, not to assign blame. Create psychological safety so people can share honestly without fear of punishment.

Questions to Help Users

• "What did we learn that we didn't know before starting this project?"
• "If we had to do this again with the same information we had at the start, what would we do differently?"
• "What signals did we see early that we ignored or missed?"
• "What systemic issues contributed to this outcome that we should address?"
• "What kill criteria should we set for similar projects in the future?"
• "How will we ensure these learnings actually influence future decisions?"

Common Mistakes to Flag

• Blame-focused framing - Turning the exercise into finding fault rather than understanding systems
• No follow-through - Running retrospectives but never acting on the learnings
• Only reviewing failures - Missing the opportunity to learn from successes and understand what drove them
• Optimizing the score, not the learning - Focusing on what percentage of OKRs were achieved rather than why
• One-time events - Running retrospectives only for big failures instead of making them a regular practice

Deep Dive

For all 13 insights from 11 guests, see references/guest-insights.md

Related Skills

• running-effective-meetings
• running-decision-processes
• planning-under-uncertainty

Post-mortems & Retrospectives - All Guest Insights

11 guests, 13 mentions

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Annie Duke

Annie Duke

"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."

Insight: A pre-mortem is only effective if it results in 'kill criteria'—pre-determined signals that will trigger a pivot or shutdown.

Tactical advice:

• 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.

Timestamp: 00:00:28

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"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."

Insight: Pre-mortems counteract the 'sunk cost' bias by establishing objective exit points before emotional attachment to a project grows.

Tactical advice:

• 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).

Timestamp: 01:06:18

Ben Williams

Ben Williams

"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."

Insight: Institutionalizing a 'learnings review' ceremony ensures that experiment data is actually leveraged for future decisions.

Tactical advice:

• Hold weekly 'Impact and Learnings' reviews focused on insights rather than status updates
• Socialize learnings across the entire company to uplevel other teams

Timestamp: 01:07:00

Carole Robin

Carole Robin

"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?"

Insight: Reframing failure as a learning opportunity is essential for long-term growth and resilience.

Tactical advice:

• When a failure occurs, immediately ask: 'What is the lesson here?'
• Use the AFOG acronym to maintain perspective during painful setbacks.

Timestamp: 01:17:02

Christina Wodtke

Christina Wodtke

"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."

Insight: The value of grading OKRs lies in the retrospective analysis of why a goal was or wasn't hit, not the number itself.

Tactical advice:

• 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%.

Timestamp: 00:53:20

Eeke de Milliano

Eeke de Milliano

"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.'"

Insight: Reframing post-mortems as retrospectives helps normalize failure and focuses the team on learning rather than blame.

Tactical advice:

• Rename 'post-mortems' to 'retrospectives'
• Shine a light on failure to mitigate the fear of taking big swings

Timestamp: 00:22:14

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"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."

Insight: Publicly celebrating the learnings from a failure reinforces a culture of innovation and psychological safety.

Tactical advice:

• Encourage teams to send 'learning notes' about failed projects to the entire company
• Have teams present failures and lessons learned at all-hands meetings

Timestamp: 00:28:18

Janna Bastow

Janna Bastow

"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?'"

Insight: Retrospectives are a primary tool for fostering psychological safety and continuous improvement within a team.

Tactical advice:

• Use retrospectives to identify what is and isn't working and empower the team to change their situation

Timestamp: 35:24

Maggie Crowley

Maggie Crowley

"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."

Insight: Failed projects often stem from skipping discovery and underestimating the complexity of technical rewrites.

Tactical advice:

• Avoid 'side-by-side' rewrites of core products
• Never skip discovery or requirements gathering for large technical projects
• Be honest about 'sunk cost fallacy' when projects go off the rails

Timestamp: 00:56:47

Melissa Perri

Melissa

"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."

Insight: Personal growth in product management requires applying the retrospective framework to one's own career and learning habits.

Tactical advice:

• Regularly audit your own 'toolbox' of frameworks and discard those that no longer serve your specific context.

Timestamp: 51:55

Mike Krieger

Mike Krieger

"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.'"

Insight: Shutting down a product requires recognizing when the 'energy' isn't in the system and having the intellectual honesty to call it early.

Tactical advice:

• 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.

Timestamp: 00:38:39

Ronny Kohavi

Ronny Kohavi

"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."

Insight: Focus retrospectives on 'surprising' results—where the delta between prediction and reality is largest—to maximize organizational learning.

Tactical advice:

• Hold quarterly meetings specifically to review the most surprising experiment results
• Analyze 'surprising losers' to uncover hidden factors like battery life impact or user friction

Timestamp: 00:17:53

Shreyas Doshi

Shreyas Doshi

"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."

Insight: Pre-mortems use a hypothetical failure state to create psychological safety, allowing team members to voice concerns they would otherwise withhold.

Tactical advice:

• 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.

Timestamp: 00:24:38