Critical Thinking in Combat - Lessons Learned
Why Character and Intellect are the Cornerstones of High Stakes Leadership
The life and death crucible of ground combat is an unforgiving classroom; there is just so much to learn, and the stakes are so high.
When it comes to high stakes leadership, there are two decisive personal attributes that differentiate success from failure – Character and Intellect – in that order.
Combat is a thinking game; I just can’t say enough or loud enough how important critical thinking and problem solving are when the risks are really high.
Let me explain.
From 2017 to 2019 I commanded our Army’s elite 3rd Ranger Battalion. The 3rd Ranger Battalion is perfectly designed and equipped for one purpose - to hunt and destroy terrorists.
By way of a very simple model - we’d deploy to Afghanistan, we’d look for terrorists, find them, and then destroy them.
Imagine a local villager walks up to the Forward Operating Base and claims that he can identify a regional Taliban leader. For a price, he’s willing to provide the location of the insurgent’s house and a physical description. (This was remarkably common). The villager describes the insurgent’s mud hut, describes that he wears a white coat and black hat, describes that he drives a yellow car, and even describes in exquisite detail that he uses a small commercial radio to talk to his neighbor insurgent buddies.
Let the hunt begin.
The first thing we do is scour Google Earth (or a similar program) to find the described house. And sure enough, we find a structure matching the description.
Then, we deploy a Scout Team to go watch the house – very similar to a stake out. We just watch…sometimes for a few days…sometimes for longer. Unblinking.
Indeed, there is military age male that lives in the house. He wears a white robe and black hat. He drives a yellow car. We sometimes see him fire up a little handheld radio to talk to his insurgent buddies.
So, we up our game. We jump on Amazon Prime, order a low-grade handheld radio, and in about 10 minutes find this guy’s favorite frequency. We started listening to him. (No, we wouldn’t order radios on Amazon Prime, but you get the idea).
Though we never hear him say any “insurgent stuff” directly – he would use a lot of ambiguous language. He’ll say things like, “We put the things in the garden.” “The visitors will be here tomorrow.” “Tell the guy across the river to do the thing we talked about.” It all sounds non-sensical, but our hired linguist describes that the nuance of the conversation is definitely suspicious.
At first glance – it all adds up. It looks like we’ve found an insurgent. We start building a plan to kill or capture him. That’s the job.
Here is where things get interesting.
Before conducting a strike operation on our identified insurgent, there is a process to ensure that we’re acting in accordance with the Law of Armed Conflict and the Rules of Engagement. We would take this process very seriously – with a tremendous amount of personal and professional care and diligence.
(It’s worth noting – there is absolutely no good that comes from violating the Law of Armed Conflict or the Rules of Engagement; those things exist for a reason, and we take them very seriously. I simply can’t overstate the precision and care that we’d use to avoid civilian casualties.)
In this scenario – the key question is whether or not we have met a required evidentiary threshold to take a human life.
Read that again…have we met an evidentiary threshold to take a human life?
It’s a lot to think about, and this is where critical thinking becomes so decisively important.
Start with…how do we define the level of objective certainty that’s required to strike?
Clearly, we’d want to be very certain. For the sake of argument, let’s say we’d want to be 90% certain that the person that we’re watching is an insurgent.
Okay…90% of what? 90% of our own personal opinion?
Perhaps there is some formulaic approach that might be helpful. There is some combination of the intelligence (evidence) that we’ve collected that might add up to a 90% degree of certainty. Afterall, the house, the person, the manner of dress, the car, and the radio are all exactly as the local villager described. That’s all pretty good – those things complimenting intelligence indictors.
Let’s pull the thread on those intelligence indicators a little bit.
Our Scout Team identified a person that perfectly matches a description given to us by a local villager. That’s it. We didn’t see anything that looked like insurgent activity, but rather only confirmed the physical description that was given to us by a random villager who walked up to our front gate.
It’s worth asking a few questions…
Who was the villager that gave us the tip? What tribe is he in? What are his equities?
What did we pay him?
Is it normal for people to use hand-held radios? (Yes.)
Who was the linguist that described the radio chatter as insurgent activity?
What have we seen that is truly differentiating? For example, almost every male in Afghanistan wears a white robe and black hat. And, almost everybody drives the same old crappy white car…that’s covered in yellow dust. And, almost everybody carries a little radio to talk to their neighbors. The truth is…the villager gave us a perfectly clear description of every male in Afghanistan. We probably would have seen the same evidence regardless of what mud compound we looked at. And, oh by the way, all the houses look the same too.
Things are murky. We use decision-making processes and systems that give the illusion of objective certainty – but the world is actually quite gray. And, we haven’t even talked about the impact of biases yet. The two that come to mind as most relevant in this scenario are Confirmation Bias and Optimist Bias.
Confirmation Bias is when we trust information that supports our existing opinions or desired outcomes. For example, “I am a Ranger, my job is to find bad guys, here is a mountain of information that describes a bad guy, therefore it must be true.”
Optimist Bias is when we overestimate our own knowledge and ability, and we overestimate our ability to generate positive results. For example, “I’ve deployed nine times, I understand the environment, I’ve seen a lot of combat, I have made a lot of good decisions, therefore I have trust in my ability to make this decision as well.”
I’ve worked through this scenario more than I care to remember; it’s stressful and intellectually taxing – to say the least.
When it comes to critical thinking in high stakes situations, there are enduring and broadly applicable lessons.
Question Your Assumptions. It’s worth asking…what assumptions must be true for my conclusion to be true? Where does the evidence come from for those assumptions? What are the risks if I’m wrong? Is there some amount of information that I can gather to turn my assumptions into facts?
Evaluate the Evidence. Where is your information coming from – and what are the incentives & equities of the person (or organization) providing you the information.
Consider Alternative Explanations. This is the most challenging, because it forces us to consider with equal weight ideas that may contradict our desired or preference outcome.
The best teams that I’ve been a part of have designated Red Teams. A Red Team is a purpose-built Devil’s Advocate – a group whose sole purpose is to provide contrarian, original, and unaligned feedback to decision maker to help them think critically and to be less susceptible to biased (and emotional) decision making.
Consider Your Biases. There is a bit of a dilemma in human decision making. The more decisions we make, the better and more confident we become. We develop decision making shortcuts and heuristics...which result in systemic biases. It’s definitely worth knowing the different types of bias – with some deliberate reflection on how they effect our decision making. Thinking Fast and Slow by Daniel Kahneman is a great first reference to understand bias in decision making.
Critical Thinking is a uniquely human endeavor. Let’s be 100% clear – Artificial Intelligence isn’t intelligent. Large Language Artificial Intelligence Models (LLM) detect patterns in written language that’s contained across the internet. It uses those patterns to predict what words or ideas might come next. It’s not creating new ideas…but rather repackaging ideas that somebody else has already had. Certainly, LLM is a useful tool with an impact that can’t overstated, but it remains limited in judgement, creativity, and critical thought.
Critical Thinking Isn’t about Education…though it certainly helps. A few years ago, one of the most educated people I know called me “anti-intellectual” in an unnecessary personal attack during a professional dialog. My crime? Questioning his assumptions. That’s called an ad hominem attack, which is a logical fallacy (and probably a different essay).
And finally…
When it comes to high stakes leadership…character and integrity reign supreme.
Our character is like a wellspring for critical thinking and decision making, it’s the foundation upon which everything else is laid. Every technique and practice that I’ve described is subject to erosion under the stress and strain of true high stakes scenarios.
Imagine the ambiguity of the combat scenario I described; there is no way to reach a perfectly known conclusion. Even with the best critical thinking framework and organizational Red Team – it’s still ambiguous. 50/50 on the decision to take a human life.
The only way to get it right is if you are leading with a perfectly clean heart and clear intent; inspired and guided by virtues like honesty, justice, and temperance.
When it comes to critical thinking…character reigns supreme.
Editor’s Note. I always use ChatGPT to check spelling and grammar. Sometimes I use its suggestions, sometimes I don’t. ChatGPT isn’t actually a great writer, and it doesn’t have my ideas. Today, for the first time, ChatGPT gave me some editorial feedback.
It wrote, “Your AI paragraph is a bit overstated. It reads more like a rhetorical flourish than a precise claim.”
Hilarious.



Great article. Character is everything!
Curious your opinion on the role of AI tools in professional communication. Where everything we send is both discoverable and we are accountable for it. I have some employees who I’ve encouraged to run emails through provided AI tools because they are communicating with public officials and recognize their own weaknesses; harsh tone, not diplomatic, etc. I’ve seen it help them tremendously and probably save me some heartburn. However I tend to shy away from using it myself, not only because of the accountability factor but also authenticity. As you point out it isn’t truly intelligent or thinking, it doesn’t capture ideas or emotion. Often I find the human elements, the vulnerability, the passion, and emotion are what makes effective communication. To be fair I have to be more strategic than tactical and my employees deal more in immediate issues while I’m at 30,000 feet but at all levels relationships matter. AI is here and not going away and I do leverage it in data analysis but very interested given your commentary on where it fits in how we communicate with other people.