So, let me tell you about this whole Anthony Caldwell thing. It’s not like some magic formula, you know? I stumbled upon his name, or rather, his approach, quite by accident a few years back. I was digging through some old company archives, looking for inspiration, or maybe just procrastinating, who knows?

Anyway, I found this really unassuming, thin folder. Inside, there were these typed-out notes, almost like a forgotten memo, detailing a process for project debriefs. At the bottom, handwritten, was “Caldwell’s Method.” I figured, “Anthony Caldwell, huh? Never heard of him.” The method itself seemed so… basic. Almost too simple to be effective, especially with all the fancy new techniques everyone was raving about at the time. I initially just shrugged it off. Too old-school, I thought.
Fast forward a few months. We had just finished this monster of a project. One of those where everything that could go wrong, did. Team morale was in the gutter, and nobody really wanted to talk about it, but we knew we had to. Our usual way of doing retrospectives just wasn’t cutting it. It was all polite nods and no real talk. That’s when I remembered that dusty old folder.
I figured, what have we got to lose? So, I decided to try and implement this “Anthony Caldwell” way. It wasn’t easy getting the team on board. They were skeptical, just like I had been. “This looks like something from the Stone Age,” one of my guys said. But I pushed for it. I said, “Let’s just try it once. If it’s terrible, we never speak of it again.”
The first step, according to Caldwell’s notes, was brutal honesty, but structured. Not just a free-for-all complaint session. It involved everyone writing down, individually and silently:
- What went well, specifically.
- What went catastrophically wrong, specifically.
- One thing they personally would do differently.
- One thing they think the team should do differently.
Then, we went around the room, and each person read out their points. No interruptions, no rebuttals until everyone had spoken. Man, that first session was tense. You could cut the air with a knife. Some uncomfortable truths came out. Some people got a bit defensive initially. I was worried I’d made things worse.
But then, something interesting happened. After the initial awkwardness, people started to actually listen. Because it wasn’t personal attacks, it was about the project, the process. Caldwell’s notes emphasized focusing on actions and outcomes, not on blaming individuals. We had to really guide the conversation to stick to that. I remember spending a lot of time saying, “Okay, let’s focus on the ‘what,’ not the ‘who’.”
We didn’t solve all our problems in that one meeting. Of course not. But it was the first time in a long while that we had a genuinely open conversation about what needed to change. We actually came away with a few concrete action items. Things we really did implement.
We used that Anthony Caldwell method a few more times after that. We tweaked it a bit, made it fit our team better. It wasn’t a silver bullet, and it didn’t replace everything else. But for those really tough, soul-searching moments, it had a rawness and directness that, surprisingly, worked. It forced us to confront the uncomfortable stuff, which, turns out, is often where the real learning is.
So yeah, that’s my experience with this Anthony Caldwell. Or at least, his debriefing method. Sometimes those old, forgotten ways have a bit of wisdom in them, you just gotta be willing to dust them off and give them a proper go. It’s all about trying things out, seeing what sticks, right?