How to run a retrospective that actually works

Six months after a project: "What did we learn from that?" You: "Uh... it was good?". Here's a way to fix that. It takes about an hour.

Perhaps you're like me - decent at capturing the obvious stuff - action items, process tweaks, what went wrong. But the richer insights? The moments where someone says something that shifts how you think? Those vanish.

Here's how to prevent them disappearing.

Step 1: Do your debrief as a conversation

Don't write it. Talk it through with your team. Real conversation, not a structured meeting. Let it wander.

(Pro tip: when you hear something magical, call it out very clearly)

Step 2: Record it

Voice memo. Zoom recording. Whatever. Just capture the audio.

Step 3: Transcribe it - properly

Use transcription software. Not a note-taking AI that summarizes. You need the raw transcript. All the umms, the half-thoughts, the tangents. That's where the richness is.

Step 4 (Optional): Mark the themes as you go

If you catch moments during the conversation, drop markers. Name them. "Thinking like Denzel Washington" was one of ours recently. (That's for another post.)

The Pro Tip from Step 1 helps here :)

Step 5: Feed it to an LLM

Export your transcript - preferably as a markdown file. Upload to your LLM of choice, ideally with some pre-training / context.

Ask it to pull out key themes. See what it finds. It'll catch patterns you missed.

Step 6: Feed it the raw transcript again

Tell it to check its work. Did it miss anything? Are the themes accurate?

Step 7: Manually review

Sorry. You still have to read it yourself. The LLM will get 80% there. You're looking for the last 20%.

Step 8: Use it

You now have LinkedIn posts, language for your next pitch, learnings for your team, and a real artifact of what you built.

Lovely.

One caveat:

Without Step 1 - a real conversation with real people about a real project - none of this works.

You can be great with AI tools. But the actual skill is in critical thinking, synthesizing ideas, and active listening.

The tools just help you remember what you already knew.