Revenue Operations Chief Revenue Officer

Building Better Teams, Just Like a General

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Anne Miller
Managing Editor



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Banner image with headshot photograph of General (Ret.) Stanley McChrystal
Banner image with headshot photograph of General (Ret.) Stanley McChrystal

Revenue operations and sales teams sometimes liken themselves to soldiers on a battlefield. General (Ret.) Stanley McChrystal takes that analogy a step further, based on his experience as the commander of U.S. forces in Iraq and Afghanistan at the height of America’s involvement there. 

During his service, with enemy forces shifting to small, fast, decentralized, flexible, and disorganized guerrilla units, McChrystal realized the top-down sign-off and approval machine of a traditional military structure no longer fit the situation on the ground. As a civilian, he sees parallels with the demands of modern hyper-growth technology and revenue fields. 

“Every organization is now operating in that environment, which means we've got to have a different set of qualities since instead of predictability and efficiency, we've got to be really fast and we've got to be very adaptable,” he says. 

McChrystal spoke at Generation Revenue 2021, Clari’s virtual conference focused on the future of revenue operations. McChrystal, a retired four-star United States Army general, helmed the Joint Special Operations Command in the early 2000s. He is a founder and partner of the McChrystal Group, which advises executives on managing change and building better teams. He wrote the book “Team of Teams,” about organizational structures and leadership that maximizes independent yet cross-functional decision-making and empowers teams outside of hierarchies, reducing systemic friction and leading to increased success.

Clari’s Chief Revenue Officer Kevin Knieriem, led the conversation with McChrystal.  GenR2021 was a must-attend event for sales and operations leaders who are leading change by committing to transparency and rigor. They believe in transparency and accountability, and they seek to break down silos, collaborate with peers and have productive, data-driven conversations that drive real outcomes for the business—beliefs McChrystal’s work emphasizes. 

“Traditional militaries were designed to get large groups of relatively young people do something that was unnatural, go in harm's way and do it in a tight group,” McChrystal says. “That required a lot of discipline. That required a lot of efficiency. That required a process. All of those things with somebody in charge that was brilliant.”

But then came Iraq, where the other side might seem disorganized, but they were lethal, fast, and constantly adapting. 

“We walked away with a hypothesis that what we'd gone through, was it unique to a war? It wasn’t,” he says. “It was a reflection of a modern environment. And that modern environment says that things are faster. There are more variables, and it increases the complexity, and that's not limited to any single organization. 

Building Trust, Removing Checklists

First, McChrystal says, his teams needed motivation—a shared purpose. Then, they needed trust. Of course, men and women in combat learn to trust their teammates in ways that only life and death situations can generate. At the same time, those teams didn’t operate in silos, yet sometimes acted like it. Beyond the confines of those small teams, trust, teamwork, knowledge and support could fall off a cliff. 

“In our forces, familiarity doesn't breed contempt. It actually breeds trust, but they didn't know each other. So we started by taking really effective operators who were influencers in their own world and cross attaching them to other organizations, not for a day, but for months at a time.” 

Not everyone liked the plan, but after their rotation, the cross-pollinators would return and say—those other folks? They’re just like us. 

“Trust extrapolated,” he says. “When you match it with a common purpose, they're all trying to get the same thing done and they trust the intentions and the capability and the other. Then you start to see real progress.”

Take a football team, he says. A coach can set the plays and send the players onto the field, but the opposing side doesn’t always do what you plan for. And the coach is sidelined. But if the coach has empowered their players to lead and respond in the moment on the field, everyone doing their jobs and working with each other, they can react quickly and as one. 

Manage for the Blinks

In the military, McChrystal developed a cycle called find, fix, finish, exploit, and analyze, for projects and reviews. But just as there’s a comma between each word, there’s breaks, or what the General calls blinks, between each step. The solution was radical communication. 

“We brought all of that organization into the same ecosystem. We shared the information all the time. We connected them diagonally and talked about everything. And what happened was as everyone understood the context and what mattered, you start to build trust.” 

And you close the blinks. 

Take, for example, intelligence material. McChrystal spoke about bags of papers and other material his troops would risk their lives to collect from the field. Sometimes those goods sat for days before anyone started reviewing the information. Some of the information would already be stale. By pushing the cycle, reducing top-level reviews, empowering staff to power through quickly, the time from find to finish and exploit could diminish radically. 

Another step that helps: collective intelligence, or pushing the ability to make decisions much closer to the point of action.

In the military, soldiers cycle out of posts every few months or years, so they’d approach their jobs with a narrow frame of reference. When McChrystal asked them how they’d handle the work if they weren’t going to leave, their perspective changed. No longer about short wins, they started viewing the whole picture, and laddering up to that.

Layer on top of that a leader who empowered them to make their own decisions, and they felt more ownership, while reducing response times. For McChrystal, that meant removing himself from the decision process sometimes, and trusting his own people. 

“Their answers were sometimes very different from what I was seeing 300 miles away in the headquarters in Kabul (Afghanistan). I had to recognize that I've got a lot more experience, but they were close to the problem. And they are pretty bright people.”

The benefits of building a network of well-trained, trusted teams empowered to make smart decisions on the battlefield is that you’ve also built a system that can pivot and flex as opportunities change. 

“If at one moment we figured something out, we pat ourselves on the back, we got promoted, we start to think that we've got the right answer— we're wrong because the problem keeps shifting,” says Clari’s Knieriem. “Every day you go to work to lead, you're leading a slightly different organization against a slightly different problem. And so if we think that we've figured it out and everybody's got to fall in line to our leadership pronouncements, we are probably incorrect.”

If leaders force themselves to constantly evolve and adapt, just like their teams, everyone is likely to emerge victorious. That’s something all sales teams can strive for. 

Read more:

Generation Revenue: Leading Into the Future