How do a leaders know when they’ve made the right choice before the results prove them right? What does it take to effectively lead Soldiers, or to make a decision you know is right even when detractors say otherwise? For cadets at the U.S. Military Academy, these are questions that typically arise as the years go by and as cadets steadily reach the end of their tenure at the academy and prepare for big Army.

Luckily for these cadets, experienced leader, retired Navy SEAL officer and author of the New York Times bestseller, “Extreme Ownership,” Jocko Willink sat down for a virtual Microsoft TEAMS interview with the Director of the Modern War Institute, Col. Patrick Howell, to lecture the future leaders on the importance of effective leadership on Friday.

Howell read a plethora of questions cadets and faculty members wrote in the chatroom. The Head Assistant Wrestling Coach at West Point, Ned Shuck, posed the question, “Can you talk about the importance as a leader to communicate the why behind what you’re asking your team to do? Especially when it doesn’t seem to make logical sense to them? And maybe even yourself?”

“I got four laws of combat: right cover, move, simple, prioritize and execute decentralized command, the basis of decentralized command is people understanding why they’re doing what they’re doing,” Willink responded. “Communicating the ‘Why’ is the basis of decentralized command. And how critical is it for you to communicate that? It is absolutely critical. It’s so critical that if you’re sending people into the field with them not understanding why they’re doing what they’re doing, you’re failing as a leader.”

Willink explained in the second part of the question, on the importance of the leader understanding the why. If the leader doesn’t understand the why — not only is he or she failing themselves and their team, they are also failing the leaders above them. The leader should see him or herself as a student to some degree still trying to learn and evolve.

“If you don’t understand, you should be raising your hand and saying, ‘hey, colonel, can you explain to me why we are doing this?’” Willink said. “Can you explain to me why you want me setting security on this corner of the city block that we’re going into, because I don’t know why we’re doing it.”

Willink added that when dealing with more complex questions that deal with strategy in relation to understanding the ‘why,’ it’s imperative to pay strict attention to detail.

For example, in Willink’s second deployment to Iraq, he along with his SEAL team got ordered to work with Iraqi soldiers. Not only were the Iraqi soldiers unmotivated, they also didn’t speak english so the communication barrier was thick between the two parties.

Willink and his team were ordered to venture out onto the most dangerous battlefield in Iraq at the time, which was Ramadi in 2006.

“And now I’m putting my guys lives in the hands of these untrained jumbies, which is the Iraqi soldiers. So, you might think, I don’t even believe it. I can’t believe — I don’t understand why we would ever do this. So, what I had to do was actually think about it. And it didn’t take me very long to figure out,” Wilink said. “OK, if we don’t train these Iraqi soldiers up to a point where they can handle the security in their own country, well, then who’s going to do it? Well, the answer is us.”

Willink added that at this point in the Iraq war, every American unit had been told at the time to work with Iraqi soldiers. American units would take two Iraqi soldiers, and attach them to 20 members from a seal platoon believing that having more Seals who can easily communicate with each other would increase their odds of getting the mission done accordingly.

“Every unit stationed in the country was doing this, and leadership got wind of that. And so leadership said “‘OK, you don’t want to do what we’re telling you to do? Let us be a little bit more clear,’” Willink said. “And so they ended up giving a ratio — from now on if you do an operation, for every one American that you have, you have to have seven Iraqi soldiers. Now, I didn’t like this because in Ramadi, many of the Iraqi units had so many deserters and so many casualties, and they had one third of their unit on leave at all times. So, there we were working with units that had 20 Iraqi soldiers. So if there’s 20 Iraqi soldiers, how many Americans can I bring? Maybe two and a half, right?”

Willink wondered who would he send from a seal platoon? He needed his medics, his radio man. He needed his Joint Terminal Attack Controller (JTAC), his Explosive Ordinance Disposal (EOD) specialist and machine gunners, among other things.

“And so, what did I do? Did I just say, ‘Well, this is what we’re getting told to do. We have to do it. It’s stupid’ No. You know what I did? I did exactly what I said. I raised my hand, I wrote an email to my boss of the chain of command and said, ‘Hey, sir, here’s what you guys are asking. I get it. Here’s the situation on the ground in Ramadi. We’re getting one to five people wounded and killed a day here. Every single time we go off the wire, we’re getting into a gunfight. We have small number of Iraqi soldiers due to the number of wounded and killed. Here’s the minimum requirement I would like to take in the field. Can I please get a waiver to bring a minimum of six seals when I send my guys out in the field? Thank you.’ My boss said, ‘Yeah, no problem,’” Willink said.

Willink said his boss ran up the chain of command and thoroughly explained the dire situation.

Leaders up in the chain of command listened and understood the peril Willink was faced with and decided to stop taking excessive risks. Willink’s determination to change the mind of his chain of command proved that asking a good question is paramount and listening to the response of one’s leadership is just as crucial.

“If I say Pat’s working for me, and I say, Pat, there’s a machine gun nest up there, take your squad, go charge it. And Pat looks at it and says, ‘oh, there’s an elevated machine gun position bunkered in and there’s open ground up hill. We’re all going to die.’ Do I want him to execute that mission still? No,” Willink said. “I want him to say, ‘hey, Jocko, wait a second, what is it you want me to get accomplished? Because if we go up that hill, we’re all gonna die. Let’s get some suppressive fire — Let’s put some mortars on it to get their heads down and we can flank them,’ So I don’t want the simple answer ‘Yes,’ I want to have people who are going to push back if what I’m saying doesn’t make sense.”

Willink added making iterative decisions quickly mitigates unnecessary risk on the battlefield. Once you make a decision as a leader, the decision is made.

A leader can’t waste time regretting a mistake made on the frontlines. A leader should focus on using that time to devise a way to fix it, Willink said.

“A leader thinks ‘hey, I shouldn’t have committed my forces there — oh no.’ Now go and square away your forces so you can maneuver them to where they need to be,” Wilink said. “If you want people to take ownership — what you do is take ownership yourself. As you start doing that — the people around will start to do that as well.”