For our project “The Uncertainty Boom,” we spoke with five experts on the effects of widespread uncertainty on our society, the economy and even the ways we think and act. 

Here, we talk about leadership under uncertainty with George W. Casey, a retired four-star general who was the commanding general of the Multi-National Force in Iraq from 2004 to 2007. His book “Strategic Reflections: Operation Iraqi Freedom” draws lessons from his time in Iraq. He currently teaches at the Cornell SC Johnson College of Business. This interview has been edited for clarity and length. 

Tell me about preparing for your mission in Iraq.

I found out on a Monday that the president was looking to put a new commander in Iraq. I found out on Tuesday that I was one of the people being considered, and I found out on Thursday that I was picked. Secretary Rumsfeld gave me 30 days to get into Iraq, to get my feet on the ground, then to come up with a plan for what we were going to accomplish.

Right in the middle of doing this, we get thrust into a major battle across the southern part of the country because a young Marine, who'd been on the ground less than a week, drove too close to a militia leader's house. A gunfight broke out in the holy city of Najaf and then spread into the Imam Ali shrine, one of the holiest sites in Islam. Now we've got this major battle going on at the same time we're trying to figure out what the heck we're doing. 

There's always an element of uncertainty. From the time I was a lieutenant, commanding a platoon of about 30 guys, I was always trying to figure out what the next step was. And it just became built into how I thought about things, that we may not know exactly what we're doing but we'll figure it out. And that mind-set became ingrained in me over time.

How did you adapt to that particular situation?

The American military hadn't done counterinsurgency operations since Vietnam. So now we find ourselves in a counterinsurgency environment with a bunch of soldiers like myself, who had done nothing but fight conventional war for 30 years. And there was nobody left in the military who had that practical hands-on experience of fighting a counterinsurgency.  When I got there, we weren't even talking about insurgency. There was a quote from Rumsfeld saying that they're not insurgents, they're just a bunch of “dead-enders.”

So I brought some academics and we did a study of counterinsurgencies in the 20th century, and we came up with a list: things that successful counterinsurgencies did, and things that unsuccessful ones did. We started up our own counterinsurgency academy in Iraq where every captain and above coming into Iraq spent a week in that academy. Then I partnered every US unit with Iraqi military [units] and made them responsible for the Iraqi unit's success. 

How did you separate long-term goals, like your training academy, from the demands of the immediate situation? 

This gets at the bifurcation of the brain. On the one hand, I had an understanding that the changes I needed to make were going to take time.  That was the right part of my brain. On the left part of the brain, I had to put in place the strategy that the soldiers on the ground could execute today with the resources that we had, knowing that I had to continuously adjust that strategy. I had to shift their mind-set away from being very good at conventional war in which you succeed by applying force against your enemies. While that is somewhat useful in counterinsurgency operations, if you're not careful you create more enemies down the road, which is what was happening.

Something that I find is very prevalent today is leaders dealing with something fundamentally new. Leaders didn't have experience in dealing with Covid. Everybody had to figure it out together. It requires a different mind-set in the leader. 

One of the things that probably won't surprise you as I was coming up in the military is our leaders conveyed to us this notion that they were omniscient. Once I got to that position, I realized that the higher you go, the less you know, And the more you have to be comfortable dealing with uncertainty.

How do you personally deal with constant uncertainty?

Because the environment in Iraq was so overwhelming and so uncertain, it honestly put me on my back foot for a period of time. You make bad decisions when you're defensive. One of the big mental transitions I had to make was to stop trying to figure out the exact way things are going to come out. Because you never will. Find what you want to accomplish, then make a plan and move yourself in that direction.

In the army, we say there are only two kinds of plans: those that might work and those that won't work. The best we're gonna do is a plan that might work. People spend so much time seeking certainty. It’s a fool’s errand. 

Give me an example from your time in Iraq. 

We had seven months from the time I got into Iraq to have the first free elections in 50 years. I wasn't sure we were going to be able to figure that out. But we studied the problem and we asked, “What are the three to five most important things that we have to do to prepare the Iraqis to do this?”  And we worked it out.

What I find dealing with uncertainty is that my mind worked iteratively. I didn't just walk in there and look at this and say, OK, this is what we're going to do. It took 30-plus days of me working my way around the country talking to different people, getting different insights and putting a plan together to get those elections done in January of 2005. Then we laid those things out on a timeline and said, “OK, these are the things we have to do.”

You had excellent people working under you. Why not rely on their reports? 

Because I had to visualize it in my own mind. One of the biggest things about dealing with uncertainty is you have to get it straight in your own head first. You should be informed by your staff. But not driven by them.

One problem with staff [recommendations] is that you get a consensus view. Well-intentioned but not necessarily hard critical thinking. So I would take them back through the problem. “What options did you consider that led you to this conclusion?”  If someone came in and said, “This is what we've looked at. Here are three options,” that's a better answer than “Here's what we should do.”

You also established a red team in Iraq. Talk about the army's use of red teams.

Whenever we do war games, the good guys are blue and the bad guys are red. And so it's common practice for us, once we put a plan together, to put together a small group of folks that operate outside of the normal staff process and say, “OK, you guys are the enemy commander. Look at our plan from the enemy's perspective.” In Iraq, I took this group of smart folks outside the staff process — people from the CIA, the Foreign Service, the British Embassy. 

We routinely used the red team to think ahead. For example, we asked the red team, “What's the security situation going to be like in the aftermath of the elections?” I got the CIA station chief to put somebody in charge because the CIA cared less about what I thought. In fact, they loved to put their finger in my eye and tell me things they didn't think I wanted to hear. But it gave us alternative views and that was the important thing.

How do you then reconcile those points of view?

You have to do it in your own head. After I'd been there about a month, I needed some time  alone to sort all these ideas that were ricocheting around in my head. So I started taking a day off a month getting my own thoughts together. At the end of that time, I'd write something down because it really caused me to focus my thinking. 

Wasn’t it difficult to take a day off? You're in the middle of a war zone.

It wasn't easy, but you've got to take care of yourself. You have to make sure that you don't wear yourself down. When I was just going from meeting to meeting to meeting, not thinking creatively about solutions to our problems, I knew I needed a break. 

You write that "it's hard to get strategy right in an uncertain environment.” Can you give a specific example from Iraq of being forced to adjust? 

When we started out, we came up with a vision to guide the mission. The vision was an Iraq with a representative government and security forces that could maintain domestic order. That was it.  What I've come to realize is, you know, the vision doesn't really change much. But the strategy can and should change because your situation is going to continue to change. 

About the middle of 2005, our intelligence guys came back and said, “Our most critical enemy has changed. The insurgency is not the biggest threat now. It's these Islamic extremists who are infiltrating into Iraq and blowing themselves up in Baghdad killing innocent civilians.” And so we had a change of strategy to go out and restore Iraqi control to their western borders and to disrupt what we call ratlines down the Tigris and Euphrates valleys that these folks are coming in. 

You also did write that to succeed, you had to play away from the ball. Can you talk about that?

Combat is like kids’ soccer. Everybody goes to the action. What I had kept telling myself and telling my subordinate leaders is, You need to zoom out. Don't just stay focused on the point of contact. Zoom out and look at what's happening there in the context of your whole environment. 

Since you've retired, you've taught at Cornell Business school and you've sat on corporate boards. So you must hear people reacting to AI, saying that the world is changing and that they feel lost. 

We're all victims of our experience. The real art is figuring out what's transferable from your experience and what's new. People start to talk about gunpowder, you know, and how that changed the nature of warfare. Yeah, it changed the nature of war, but over thousands of years. It didn't really have a significant impact until the people fitted in with their experience. 

That's the same thing that’s happening with AI. People don't fully understand it. Leaders don't fully understand it. I went back to Georgetown about five years ago, took a course on AI, because I couldn't figure it out. You have the early adopters that are out there but the great mass of humanity is still trying to figure it out.

The last thing I'll say is this: Until a leader gets it in his or her head about how AI can help their particular industry, until they have a deep enough understanding of how to apply it, they're just throwing money at contractors. They’re not going to be successful.

Explore other Uncertainty Boom interviews: 

Jill Lepore, the Harvard historian, talks about her new book examining how technology is affecting our liberal democracy.

Jack Nitschke, a clinical psychologist and neuroscientist, discusses uncertainty’s effect on our brains and why it makes us less prepared for the future.

Nicholas Bloom, an economist at Stanford University, discusses economic uncertainty: what it is, how it is measured and how it affects companies, countries, investors and consumers.

Kate Sweeny, a research psychologist, studies how uncertain outcomes affect our behavior and sometimes prompt poor decision-making.