Brian Chesky's Humble Curiosity

Curiosity and wisdom create powerful intergenerational collaboration, especially when older team members embrace their unique value rather than trying to fit a youth-centric mold.

At Airbnb, Chip Conley discovered that being both wise and curious was essential to his success as a 52-year-old executive in a company where the average age was 26. Rather than pretending to know everything, he approached his role with humility, asking questions when he didn't understand tech terminology while offering his hospitality expertise where it was needed.

This approach revealed the power of intergenerational collaboration. As Chip explains, "When you have older brains connecting the dots, thinking broadly, peripherally, and younger team members being really fast and focused, being able to think linearly about how to get things done, that combination can be brilliant." Younger brains excel at fluid intelligence—fast, focused problem-solving—while older brains develop crystallized intelligence that enables holistic thinking and pattern recognition.

For older professionals in tech, success comes from embracing this complementary dynamic rather than competing on the same terms as younger colleagues. The most effective approach is showing up with passionate engagement and curiosity. As Chip notes, "People won't notice your wrinkles as much as they'll notice your energy." This means maintaining both physical energy and positive energy that draws others to you.

This perspective challenges the common tech industry narrative that values youth above all else. Emotional intelligence typically improves with age, and older team members often excel at seeing blind spots and providing institutional wisdom. They can be particularly valuable in helping organizations navigate complex challenges that require pattern recognition from past experiences.

For companies, this suggests rethinking rigid roles and compensation structures. Chip proposes that older employees might consider part-time arrangements: "I'm willing to take a 20% or 40% pay cut to go to 80% or 60% time, and the company is going to get their money's worth." This flexibility allows organizations to retain valuable wisdom while accommodating different life stages.

The most successful intergenerational workplaces create mutual mentorship opportunities where younger and older employees teach each other different skills. While a younger colleague might help with technical tools, an older colleague might share insights on leadership, running effective meetings, or giving constructive feedback—creating a virtuous cycle of learning that benefits everyone.