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Successthe future of work

‘We need to trust our employees’: This billionaire CEO went from counting cars in the parking lot past 6pm to embracing hybrid work

Preston Fore
By
Preston Fore
Preston Fore
Success Reporter
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Preston Fore
By
Preston Fore
Preston Fore
Success Reporter
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October 3, 2026, 5:00 AM ET
Jim Kavanaugh headshot
As Jim Kavanaugh built World Wide Technology into a tech giant, he was once a believer that being in the office equals work. The pandemic changed his mind. Courtesy of World Wide Technology
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Jim Kavanaugh isn’t afraid to admit it: He probably hasn’t always been everyone’s favorite boss.

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The former pro soccer player-turned entrepreneur began building out World Wide Technology in 1990, growing the Missouri-based firm into an IT solutions giant with $20 billion in annual revenue. But along the way, he held a simple view of what it takes to succeed: You have to put in the work.

“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.”

Kavanaugh, who has an estimated net worth of $7.7 billion, learned that mindset early in his career. As a soccer player, that meant showing up to practice in the rain; as an entrepreneur, it meant being willing to put in long hours or cut back on vacation when the business needed him.

But as cofounder and CEO, that philosophy extended beyond just performance goals. He wanted to see employees putting in the hours, with an expectation that top performers would be among the first to arrive at the office and the last to leave—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.

But after more than three decades of scaling a technology company, Kavanaugh learned the importance of not getting too comfortable with any one way of doing things. The pandemic, in particular, forced him to rethink what he considered a sign of a strong work ethic—and how much of it actually required employees to be in the office. 

“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. 

Unlike Jamie Dimon at JPMorgan and Andy Jassy at Amazon, who have embraced strict five-day return-to-office mandates, Kavanaugh’s answer was ultimately no. Today, WWT takes a hybrid approach, with specific work requirements based on its “dynamic persona” philosophy: Certain roles and business units may be better suited to in-person collaboration, while others can operate more flexibly.

Kavanaugh said above all, he’s learned to put faith in the over 12,000 employees on his payroll.  

“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,” he 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.”

A flexible work schedule is paramount in the AI era

That philosophy may be especially relevant as AI puts new pressure on companies to move faster and increase productivity. But that doesn’t necessarily mean always giving employees complete freedom over where they work—or abandoning the office altogether. Instead, workplace experts like Kevin Rockmann, a professor of management at George Mason University’s Costello College of Business, say companies should be more deliberate about what they are actually trying to accomplish by bringing people together.

“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,” Rockmann told Fortune. He added that it can make workers afraid to leave their desks for even things like doctor’s appointments.

For Kavanaugh, the answer isn’t to choose between flexibility and accountability. It’s about finding a balance between giving employees the autonomy to manage their work and creating enough urgency to keep them motivated and productive.

“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 broader reality with how some companies measure performance. Some managers can become overly focused on inputs—such as how many hours someone spends at a desk or how many hours their car is spotted in the lot—instead of outputs, like the quality of the work they produce. 

According to Natalia Emanuel, a research economist at the New York Federal Reserve Bank, remote work has been a tool for workers to identify management practices that might have been easy to gloss over when the world was almost all in person.

Instead, she echoed Rockmann saying companies thinking about enforcing a stricter return-to-office policy should start with a basic question: “What are they actually trying to accomplish by bringing employees into the office?”

If the goal is mentorship, for example, mentors and mentees need to be in the same place at the same time. If the goal is creativity, simply requiring employees to sit at their desks may not accomplish much; companies may instead need to create opportunities for workers to interact with people beyond their immediate teams.

The same thinking should apply to remote work, Emanuel said. A caregiver may benefit more from the ability to work remotely for an hour or two each day to handle school pickup than from a single work-from-home day each week. Another employee may get more value from having the flexibility to work remotely for an entire 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, who is coauthor of the upcoming book about office work, In Person.

And if employees are going to make the commute, she said, companies should make sure there’s a good reason for it. She pointed to research by Nobel Prize-winning psychologist Daniel Kahneman that found 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 today, though, the location of work is ultimately less important than the attitude employees bring to it. Whether they’re sitting in the office or joining over Zoom, he believes curiosity, hard work, and a willingness to be part of a team remain qualities of utmost importance.

“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.

Fortune Daily breaks the traditional barrier between audience and newsroom. The show transforms Fortune’s trusted reporting into actionable, conversational, and entertaining insights for an emerging class of business leaders. Watch here.
About the Author
Preston Fore
By Preston ForeSuccess Reporter
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Preston Fore is a reporter on Fortune's Success team.

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