Kaizen vs Red Team

I rebuilt our sales comp plan from scratch. Twice (heck, maybe more). Both times after I thought I was nearly done.

I’d been running kaizen loops on the plan for days. Multiple personas, fresh sessions, the whole workflow I wrote about before. Each pass made the plan sharper. Better incentive curves, cleaner accelerators, tighter language. And then I ran a red team against it and an agent playing a behavioral comp analyst took it apart in about two prompts. There was a glaring fatal flaw I’d been polishing right past.

So I rebuilt the plan and ran more kaizen on V2. It was tighter, and I felt good about it. Then I ran another red team, this time with an agent playing a recruiter, and got taken apart again from a completely different angle. I’d sharpened the wrong plan a second time. Ugh.

That’s when it clicked that I’d been running the wrong loop. Kaizen makes things better. Red team decides if they should exist. Different jobs, different prompts, and most of the time I’d been collapsing them into one.

Kaizen is the friendly loop. You’ve decided to do the thing. Now you want it sharper. So you build a room of collaborators (Oliver reading the brief, Liz reading the timeline, the customer reading the copy) and you ask them where it wobbles. Will this make sense to you? What would you push back on? What’s missing? The agents are on your side. They want the thing to work. You leave a kaizen loop with a sharper version of what you started with.

Red team is not friendly. Before you commit, you want someone trying to kill the idea, not improve it. What’s the strongest case against this strategy? What am I assuming that, if wrong, takes the whole thing down? Who would I least want to read this draft, and what would they say? The agents are not on your side. You want them looking for blood. You leave a red team loop with either conviction you’ve earned or a decision reversed.

The prompts are not interchangeable, and that’s where most people get into trouble. A kaizen prompt names a collaborator: act as Liz reading this brief. A red team prompt names an opponent: act as a behavioral comp analyst who has seen ten of these plans fail because the accelerators incentivize the wrong behavior. Attack this plan. Run a red team prompt with a collaborator persona and you get encouragement dressed up as feedback. Run a kaizen prompt with an adversary persona and you get sabotage. Both feel like signal. Neither is.

The constraints differ too. For kaizen, I ask for the smallest change, the lowest cost, the fastest test. That forces the loop to stay incremental. For red team, I ask the agent to find the single load-bearing claim and attack only that. Otherwise you get a tidy list of ten objections that nobody’s going to act on.

One move that’s pure red team: steelman first. Before the agents attack, I have them rebuild the strongest version of my position, sharper than what I wrote. Then they attack that. If the steelman falls, my actual draft was never going to survive. Kaizen doesn’t need this. You’re not trying to kill the thing.

So the sequence is red team first, kaizen second. If the work survives red teaming, run kaizen to sharpen it. If it doesn’t, scrap it and start over. Which is what I should have done with V1 of that comp plan instead of polishing it over and over and over again.

AI: 40% | Human: 60% — Jesse wanted to turn his experience rewriting a comp plan several times into a blog post; AI kept losing his voice