Tim Ferriss: I’ve so many follow up questions. We spoke about this in one of our prior conversations, but I think it’s a concept worth revisiting. And that is the concept of the red team or red teaming, would you mind just describing what that is? Because I think it’s even as a thought exercise, and sometimes it’s difficult to take on both parts as a single person because you’re too close to your systems, too close to your problems. But would you mind describing what a red team is?

General Stanley McChrystal: Sure. It’s essentially making somebody the bad guy and commissioning them to screw you up. And you say, “Well, why would I do that?” Because we become blind to our vulnerabilities. There’s a great story from a war game called Millennium Challenge, which happened before the first Gulf War. And a marine general named Van Riper, lieutenant general, was made the commander of the opposition essentially in a red team role. And he looked at how this was likely to play out because he was playing a Mideast nation. And so, he said, “I’m not going to let the Americans do what they’re good at, I’m going to do a preemptive strike.” And so he did a preemptive strike in the game, he killed the equivalent of 20,000 Americans. And he really screwed up the American plan and so they stopped the war game. And they recocked him, went back, and they said, “Okay, we’re going to continue, but don’t do that again.”

And it was like, wait a minute, the whole idea of a red team is to find clever people who will come and find the holes in your plan. Where are there gaps and seams or flaws that you have become blind to? Where will they, as you inflate, it’s that tire inner tube that you’ve been working on and you patched you inflate it and you see if there are any more leaks, where are the leaks? A good red team is people who are a step outside your organization, you can have people inside, but they have to be fenced off and so that they are not wedded to the plan. Because if they’re wedded to the plan, they’re incentivized not to find flaws in it.

And so you’ve really got to have a red team that’s incentivized to find flaws, and then the leadership has got to act on those. When they find those problems, gaps and seams, the leadership has got to follow up and got to close them. And they can’t make the red team pariahs, they can’t say, “You people are bad people because you’re disloyal to our plan.” No, the greatest loyalty you can ever do is to make it stronger. And so, I’m a great believer that red teaming takes us out of being comfortable and we’re all guilty.

I remember that as a commander in combat, you’d work a plan for a long time, you’d do all these things and if somebody questioned it or poked a hole in it right when it was time to execute, you got mad. Because dammit we’re about to execute this plan, don’t distract me, don’t do that, that’s irritating. But you need them to do that. And so, red teams are really effective way to the pressure test.