All Industries, All Topics, Webinar Recap

Gen. Stanley McChrystal: Spread Leadership Through Your Organization 

User IconPat McManamon
Clock IconMarch 29th, 2021
Glasses Icon6 Min Read
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Gen. Stanley McChrystal sat in a wood-paneled office as he spoke. He was dressed in a casual professional look, a bookshelf over his shoulder dotted with works on leadership and strategy. 

Speaking on ServiceTitan’s Growth Series of webinars, the former four-star general offered wisdom and insight with an officer’s clarity and focus, gleaned from decades of in-the-field experience at the highest levels of the United States military.

McChrystal started his presentation by saying “I’m Stan.” He ended with a bit of history involving British Admiral Willian Nelson. The bookends illustrated McChrystal’s belief in leadership that empowers everyone. The “Stan” comment was genuine and self-effacing, the history of Nelson illustrative.

In the battle of Trafalgar in 1805, Nelson used his fleet in a unique way when facing the French and Spanish fleet of Napoleon Bonaparte. In sending his ships in a T-bone fashion into the enemy and directly into fire, Nelson hoped to cause chaos by splitting the enemy fleet. Nelson placed himself in the first ship, in harm’s way. He was felled by a shot into his neck, and spent two hours hanging onto life.

“From after the first moments of the fight, the person who was the architect of it and the leader of the English fleet could take no part in it,” McChrystal said. “But he didn't have to. He’d already created an organization through his leadership that was capable of getting the job done.”

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Trust, communication, empowerment

Leadership, McChrystal stressed, is about trust and communication and, perhaps more than anything, empowering those who work with and for you to be able to express themselves and take actions.

McChrystal’s keynote talk for the Growth Series was a special opportunity for ServiceTitan, kicking off its free, eight-part masterclass for the trades. McChrystal’s insight came from a unique perspective, but applies to any entity and business.

His vision of leadership shows rare combinations of qualities. He showed confidence and humility. He expressed the ability to be knowledgeable yet admitted he didn’t have all the answers. And he had the self-awareness and knowledge to expect those with and under him to contribute wherever possible.

McChrystal, now the CEO of The McChrystal Group, used his past experience as the leader of the Joint Service Operations Command (JSOC) in the U.S. military to explain his beliefs.

JSOC was formed in 1981 to create a talented unit focused on counter-terrorism. The unit was extremely effective – until it faced Al Qaeda in Iraq, which did not use a traditional command structure and had little predictability. 

“We were losing the war,” he said. “We were completing certain tasks, but we were losing the fight.”

Leadership can be exhausting, because sometimes people forget that if you want to be a good leader, you need to first be a good follower.”

Gen. Stanley McChrystal

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‘Empowered execution’ changes the game

So McChrystal changed the approach, offering an entirely new method to the team. His effort: To establish what he called empowered execution. And he did it by communicating pointedly and directly with every member of his team.

“We said, ‘Here’s what we want,’” McChrystal said. “If you get an order and the order we gave you is wrong, execute the order we should have given you.

“And they said, ‘Wow, that's throwing a lot of responsibility down on young and maybe less experienced people.’ And the answer is, that's right.

“Now, what we have to do is we have to tell them what we're trying to achieve in general. And then they can adapt their actual actions to try to best accomplish that.

“We also have to accept responsibility. If they do something different from what we might've expected them to do or had specified initially, we own it. We can't say, ‘Well, it was done down there.’

“No, we own it.”

In explaining the plan, McChrystal was honest about admitting he didn’t have every answer. 

“I did the big hand wave and I said, ‘We're going to do whatever it takes to win. We're going to try everything we can think of. And everything that works, we'll do more of, everything that doesn't work, we'll stop’" he said.

“And then I looked at them and I said, ‘You're going to figure it out. We as a team together, but I need you guys to figure it out. So let's start it already.’ And that turned out to be very effective at unlocking participation.”

What he did was set aside the known, the status quo. And he dared those with him to contribute and come along. He pointed to Dick Fosbury, who revolutionized the Olympic sport of high-jumping by going over the bar head first and backward — the now well-known Fosbury Flop. And he pointed to Walt Disney, who eschewed the status quo with a movie that seems simple but was actually revolutionary: An animated version of Snow White.

Find what’s effective, not what’s comfortable

McChrystal said there was no option but to change; what mattered was doing what was effective, not what was comfortable.

“The worst outcome is happening right now,” he told them. “There was no risk if we were already losing.”

Part of communication means setting priorities. McChrystal understands we all are faced with a laundry list of demands; he said it’s up to leadership to communicate the top two or three priorities that must be completed.

He also understands that while one person can unite or energize a team, the work is done by everyone together.

“We used to tell people in the military, the middle of a firefight is not the time to start to build a relationship,” he said.

That leads to empowered execution at every level of an organization, because that, he said, is where “the battle is going to be won or lost.”

“It's where you're actually getting things done that matter, whether you're winning the battle, making money, accomplishing tasks,” he said. “And empowered execution is more than just telling people below, ‘OK. I want you to make your decisions and do things.’ You have to empower them, not just with the authority, but with information and contextual understanding that we typically didn't do before.”

On the website of some organizations, the CEO or founder has his or her own page or highlights. On The McChrystal Group’s web page, every member of the team is listed in alphabetical order, with the same sized picture that links to the same length bio. The CEO is between the Director of Human Resources and Director of Sales.

“Leadership can be exhausting,” he said, “because sometimes people forget that if you want to be a good leader, you need to first be a good follower.”


Registration for the Growth Series is still open. Those who register can watch live, or see every episode, including McChrystal, on video replay.


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