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Brian Chesky’s Lessons on Trust and Management

In the early days of Airbnb, Brian Chesky and his team were trying everything to get the company off the ground. The young startup wasn’t the household name it is today, and the team was hustling to figure out what strategies worked best. One bold move Chesky made was hiring remote contract salespeople to help find potential property listings through Craigslist. Their mission was to reach out to property owners and get them to list their homes on Airbnb.


Chesky’s instructions were vague, though—he simply told the team to look for interesting properties. This lack of clear direction would lead to some unforeseen problems.


Brian Chesky, CEO, Airbnb
Brian Chesky, CEO, Airbnb

Photo: Getty Images


The Downside of Loose Guidelines

Without much supervision or defined rules, the contract salespeople began contacting property owners who weren’t interested in listing. As Chesky puts it, they “took things a little too far.” It wasn’t until much later that the team became aware of this issue, and by then, the strategy had already started to falter.


What’s worse is that the salespeople weren’t particularly effective in their role. Their impact was minimal, which is probably why Chesky hadn’t been keeping a closer eye on their work. The strategy quietly unraveled in the background, and eventually, it was terminated altogether.


The Importance of Hands-On Management

This experience taught Chesky an important lesson: no matter how much autonomy you give your employees, you must still maintain a close connection and provide consistent oversight, especially when your company is still young and growing. Trust is essential, but it must be earned through communication and shared understanding of goals.


Chesky realized that if you give people too much freedom without knowing them well, things can easily go off course. This is particularly true for remote workers, where physical distance can add an extra layer of difficulty in maintaining control.


Building Trust Without Micromanagement

Brian Chesky’s story is a prime example of the delicate balance leaders must strike between trust and management. On one hand, you don’t want to micromanage your team; autonomy can empower creativity and innovation. On the other hand, if you don’t provide enough guidance or structure, things can quickly spin out of control.


For Chesky, the solution was clear: if he wanted to give his team independence, he needed to know them deeply and trust them completely. This level of trust comes from constant communication, shared values, and a clear understanding of the company’s mission.


A Lesson in Leadership for Startup Founders

Chesky’s experience offers a valuable lesson for all startup founders and leaders: growth requires experimentation, but it also demands hands-on leadership. Being too distant or giving too much autonomy too early can backfire. Instead, leaders should stay involved, guide their teams, and ensure that everyone is aligned with the company’s vision and values.


This story serves as a reminder that as much as autonomy is celebrated, it must be paired with trust, and trust is built through consistent management, especially when navigating the turbulent early days of a startup.


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