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

Jim Kavanaugh, the billionaire CEO of World Wide Technology (WWT), has evolved from being a strict, long-hours proponent to championing flexible work arrangements. Kavanaugh, a former soccer player and entrepreneur, built WWT into a $20 billion IT solutions firm with an estimated net worth of $7.7 billion. He once demanded employees be at the office until after six in the evening on Fridays, but after three decades of growth, he questioned whether this was truly the best approach.

The COVID-19 pandemic forced Kavanaugh to reevaluate his stance on mandatory in-office work. Unlike some CEOs who mandated strict five-day return-to-office policies, Kavanaugh embraced a hybrid work model. WWT now tailors work requirements based on a "dynamic persona" philosophy, allowing some roles and business units to collaborate in-person while others operate more flexibly.

Kavanaugh believes in the importance of trust and work ethic, but he also acknowledges the need for flexibility in the AI era. Remote work has exposed how companies measure performance, often focusing too much on inputs like hours spent at a desk rather than outputs like the quality of work produced. Natalia Emanuel, a research economist, suggests companies ask what they're actually trying to accomplish by bringing employees into the office.

Depending on the goal—mentoring, creativity, or focused work—a clear-eyed understanding of needs will lead to a more satisfying office policy.