How do you structure pre-mortems and post-mortems with stakeholders to turn friction points into process improvements?

One of the things I'm most consistent about is the post-mortem. We do it after every major event — and Company Kickoff is a great example because we run it every quarter, four times a year, so we're constantly iterating. We bring everyone together — my team and all the stakeholders who touched the project — and we get honest about what could have been better. It all goes into a Slack Canvas, which has become our institutional memory for that event. The next quarter when we spin up planning, that ...Read More

I'm a big fan of both, so I'm glad people are thinking about them — though I'll admit I call it a "prep" before and a "retro" after, just to keep things a bit lighter than "postmortem" suggests. The real work happens in how you structure these conversations with stakeholders. At its core, you're trying to align with senior leadership, and that requires truly understanding three things upfront: your audience, the specific topic, and what decision actually needs to be made. Then you ruthlessly sim ...Read More

To turn friction into progress, the pre-mortem uses "prospective hindsight." Gather your leads and say: "It’s six months from now and this launch failed. What went wrong?" In large teams, this gives people permission to flag risks, like a lack of customer proof points or a delayed product beta, without sounding like "naysayers." These risks are then, ideally, converted into specific tasks in the project plan, solving problems before they exist. Post-mortems must be strictly blameless to avoid de ...Read More

To me, this is all about making sure your stakeholders and teams capture the right feedback, that you have a high-trust group who feels they can share that feedback, and that you get very specific about which feedback is worth actioning and who owns it.  Capture friction in real time, not after the fact - When you start a process, tell people to start a running note on their phone or laptop where they can quickly jot down pain points during the process. Any time our team starts writing a keynote ...Read More

Pre-mortems work well when they're set up for success. Here are a couple of ideas that work for me: 1. Align on what you're going after before the pre-mortem. Circulate the definition of the new focus area, who you're pursuing, and what success looks like ahead of the meeting. Get sign-off. If people see it differently, sort that out first. The pre-mortem itself should be spent identifying risks and gaps, not debating step zero.2. Bring in the Customer Voice. Start the pre-mortem with the ideal ...Read More