What military leadership teaches about team decision-making: John O’Donnell

The clearest lesson John O’Donnell carried from the military into business is that strong decisions are rarely the result of solo acts. Before a cobra attack helicopter ever left the ground, a much larger team had already made the mission possible.

O’Donnell may have been one of only two pilots flying the aircraft during his eight years in the United States Marine Corps, but maintenance crews, planners and other players all played a critical role.

"I realized very early on that you don’t accomplish anything by yourself," he tells The CEO Magazine.

"Once I entered the business world, I took that with me. I try to be as collaborative as I can with my team and across the institution."

The lesson has traveled with him through leadership roles at Goldman Sachs, The Walt Disney Company, GMAC and Allstate. Today, as President and CEO of Pinnacol Assurance, O’Donnell leads Colorado’s largest workers’ compensation insurer, protecting the workforces of more than 45,000 employers.

Empowered to act

Collaboration, however, doesn’t mean waiting for consensus before acting. O’Donnell’s military experience also taught him that even the best-laid plans rarely survive unchanged once circumstances shift.

"Commander’s intent" ensures people understand what ultimately needs to be accomplished even when the original path toward it is no longer possible.

"People have to be equipped to make decisions and take decisive actions on their own," he explains.

"They understand the mission very clearly, but there’s a lot of autonomy, empowering them along the way."

At Pinnacol, such autonomy is possible because the mission is clear enough for teams to respond intelligently to change while keeping the organization moving in the same direction.

"We have a clear and straightforward mission, which is to provide caring protection for employees and their workers in Colorado," O’Donnell says.

"That’s always our north star. When things shift and markets change and when there are different pressures and competitors, we always go back to that."

It’s a foundation that has served Pinnacol well over its 110-year history. And with the company now reaching nearly one million Colorado workers, it carries even greater weight.

"We operate with a strong mission to do well by doing good," he says. "At the heart of that is making sure we’re there for the employers and communities that rely on us.

"That means we provide coverage regardless of an employer’s risk profile. We won’t turn anyone away."

Protection through prevention

Caring for workers after an injury remains fundamental to Pinnacol’s purpose, but O’Donnell firmly believes their responsibility begins much earlier.

"We have, by far, the largest investment in safety programs in the state of Colorado," he points out.

"So with every policy, we offer a free safety inspection to make sure that injuries are minimized in the first place."

The company’s safety consulting and education programs, including specialized services for Spanish-language workers, have contributed to roughly 20 percent reduction in workplace injuries and illness over the past decade.

Fewer injuries mean fewer people facing time away from work – and employers also benefit from reduced disruption and costs. When Pinnacol succeeds in keeping injuries low, its mutual structure allows that success to flow back to its members.

"We’re proud of the value we’ve been able to return to Colorado employers," O’Donnell says.

"Over the past 10 years, Pinnacol has returned more than US$415 million to employers through general dividend payments, which is a powerful reflection of our commitment to shared success with our members."

At the same time, the company has achieved some of the strongest member and injured-worker satisfaction results in its century-plus history and consistently ranks among the top two percent of United States property and casualty carriers according to Ward’s 50.

O’Donnell views those outcomes as interconnected rather than competing priorities.

"We see ourselves as a steward of the community," he says.

Investing in tomorrow

That stewardship, O’Donnell insists, also means looking beyond the workforce Pinnacol protects today and considering who will lead the industry tomorrow.

"Insurance has long had an age problem. There are a lot of tenured people in our field, and we need the next generation of leaders," he says.

"We knew we had to start thinking differently about how we bring young people into the industry."

That thinking led the company’s leaders to look beyond Colorado. Around nine years ago, they traveled to Switzerland to study its renowned apprenticeship system, in which approximately 70 percent of young people participate. They returned convinced Pinnacol could build a version of its own.

Launched in 2017, the resulting three-year apprenticeship gives high school students – often from under-resourced schools – a combination of classroom learning and paid, hands-on experience across functions including finance, marketing, technology and claims.

"Students earn 2,000 hours of paid work experience and graduate with zero debt and a career with a proven track record," O’Donnell says.

The results have been tangible. Since the program began, 65 apprentices have graduated, with 18 going on to join Pinnacol as full-time employees.

"We’re proud to make this investment in these students, the community, Colorado’s educational landscape and the future of the economy," O’Donnell says.

"These students are our future leaders and entrepreneurs. And even when they choose to work elsewhere – we’ve seen them go on to companies like Geek Squad and Meta – we still count that as a success."

The model has even attracted attention well beyond Pinnacol, he points out. Elected officials, cabinet officials, Harvard Business School and overseas delegations have visited to learn from the approach.

Ideas from everywhere

O’Donnell explains this same philosophy also applies to embracing new technologies.

When AI tools became widely available, Pinnacol didn’t leave experimentation solely to its technology team. Instead, the company invested in access for employees throughout the business and encouraged them to explore how technology could improve the way they worked and served members.

"We work very closely and collaboratively, training people to use these tools and empowering them to come up with innovative ideas, which has really helped us to evolve as a business," he says.

"It’s amazing to see how creative people have been in using those tools to develop prototypes that have, ultimately, become mainstream solutions the whole organization can use."

Creating an environment where people are comfortable speaking up – including when they disagree with him – is central to O’Donnell’s leadership style.

"Many times I’ve had my team convince me that I’m wrong about something," he says.

"As a leader, you don’t have to have all the answers. You don’t need to be the smartest person in the room.

"Everybody who works for me knows a lot more about their role than I do. I’m just here to remove barriers and provide the opportunities and tools they need to succeed."

Beyond insurance

Pinnacol extends that sense of responsibility beyond its own walls. In fact, O’Donnell shares that more than US$7.2 million in grants has gone to community projects over the past decade, while the Pinnacol Foundation has awarded US$7.4 million in scholarships to more than 800 students with family members who were injured or lost their lives at work since 2001 – regardless of whether their families were insured by Pinnacol.

Ultimately, O’Donnell sees the company’s role as broader than insurance alone. In his view, it should shape a Colorado that benefits both people and businesses.

"What I would love to see is a safer, thriving workforce, with opportunities for people to build their futures and for small businesses to grow and achieve their goals here in Colorado," he says.

"And we want to be a key partner in helping them turn those goals into reality."