WWT's Billionaire CEO Trades Parking-Lot Patrols for Hybrid Trust

World Wide Technology CEO Jim Kavanaugh once joked with his executive team that on a Friday evening, a snow plow shouldn't be able to cross his parking lot without hitting a car. Today, the billionaire cofounder of the $20 billion IT solutions giant says trust—not attendance—is what drives his company.

Kavanaugh built the Missouri-based firm from scratch starting in 1990, scaling it into an IT powerhouse with $20 billion in annual revenue and more than 12,000 employees. Forbes estimates his net worth at $7.7 billion. Along the way, he held a simple creed: greatness requires hours.

"If you want to be great, you can't put in an average or sub-average level of input and work ethic," Kavanaugh told Fortune. "You don't get to great that way."

He learned that mindset early. As a professional soccer player, it meant showing up to practice in the rain. As an entrepreneur, it meant long hours and skipped vacations when the business demanded them. As a boss, it meant expecting top performers to arrive first and leave last—even on Fridays.

"I'm looking at cars in the parking lot, and I would literally joke with the executive team, 'On a Friday if it's not after six, I don't want to be able to drive a snow plow through here and not hit any [cars],'" Kavanaugh said.

The pandemic changed his calculus. After more than three decades of scaling a technology company, Kavanaugh confronted a question that has split corporate America: mandate the office, or adapt?

"I had to think differently about, am I going to come back and mandate all of our employees have to be in the office 100% of the time?" he said.

His answer was no. Unlike Jamie Dimon at JPMorgan and Andy Jassy at Amazon, who have imposed strict five-day return-to-office mandates, Kavanaugh kept WWT hybrid. The company's "dynamic persona" philosophy sets work requirements by role and business unit: some functions suit in-person collaboration, others run flexibly.

"I still believe in work ethic, and putting the time in and doing whatever it takes to get the job done, but at the same time, culturally, we need to trust our employees," Kavanaugh said.

"We treat our people with a level of trust, like adults. And if you need to go run your kids to a doctor's appointment or school or do different things, and you need to work later at night—you do what you need to do, to get the job done."

Flexibility meets the AI era

That stance may prove especially timely as AI pressures companies to move faster and lift productivity. But workplace experts caution that flexibility does not mean abandoning the office—or granting complete freedom over location. The real task, they argue, is defining what in-person work is supposed to achieve.

"When you're forcing people to come in, you're basically telling them that you don't trust them, and a lot of employees are sensitive to that," Kevin Rockmann, a professor of management at George Mason University's Costello College of Business, told Fortune. He added that mandates can make workers afraid to leave their desks even for doctor's appointments.

Kavanaugh frames the challenge as balance: give employees autonomy to manage their work while creating enough urgency to keep them motivated.

"If you could create that urgency and excitement, that can be a very energizing, productive culture and environment," Kavanaugh said. "If you do it to a point where people are paralyzed because of it, that is very counterproductive. So, I think there's an art and science of how you're building that structure."

The pandemic also exposed a flaw in how some companies measure performance. Managers can fixate on inputs—hours at a desk, hours a car sits in the lot—rather than outputs like the quality of the work produced.

Natalia Emanuel, a research economist at the New York Federal Reserve Bank, said remote work has helped workers surface management practices that were easy to gloss over when nearly everyone worked in person. She echoed Rockmann: companies weighing stricter return-to-office policies should start with a basic question—"What are they actually trying to accomplish by bringing employees into the office?"

The answer changes the design. If the goal is mentorship, mentors and mentees need to share time and place. If the goal is creativity, forcing employees to sit at their desks accomplishes little; companies may need to create chances for workers to interact beyond their immediate teams.

The same logic applies to remote arrangements, Emanuel said. A caregiver may gain more from working remotely for an hour or two each day to handle school pickup than from a single work-from-home day per week. Another employee may get more value from a full remote week.

"A clear-eyed understanding of what we're solving for ends up making a much more satisfying in-office policy than just plopping down X/days-per-week," said Emanuel, coauthor of the upcoming book about office work, In Person.

If employees must commute, she argued, companies should make it worth their while. She pointed to research by Nobel Prize-winning psychologist Daniel Kahneman showing commuting ranks among the least enjoyable parts of the workday.

"Commuting into the office only to sit on Zoom calls all day is a truly demoralizing and pointless endeavor," Emanuel said.

For Kavanaugh, location now matters less than attitude. Whether employees sit in the office or join over Zoom, he prizes curiosity, hard work, and a willingness to be part of a team.

"I can tell you the odds of you being recognized and being received when you go into an organization with the attitude of wanting to learn and to want to work hard and to be part of a team—those are things that kind of stand the test of time," he said.

As AI reshapes productivity expectations, WWT's bet is that trust and urgency can coexist—and that executives who keep counting cars in the parking lot are measuring the wrong thing.