As Airbnb has grown from a startup into a global tourism enterprise, CEO Brian Chesky has come to realize that founding a company and managing it are two distinctly different tasks.
Chesky discussed the steep learning curve they faced during the expansion process of Airbnb in the podcast program How I Built This that was broadcast on Monday.
“I feel like I’m almost naturally born to be a great founder, but I’m naturally a terrible CEO,” Chesky said to podcast host Guy Raz.
Chesky indicates that being a founder is more intuitive for him, whereas becoming a CEO requires a completely different set of skills.
“When you were just a child, you were already making things, creating things. You’ve actually been practicing how to be a founder all along, so when you start a company, it’s probably not your first attempt at creating something,” said Chesky.
He said that from a young age, he began to cultivate the instincts of a founder—everything from designing and taking apart toys to persuading friends to buy what he sold.
But he said that when he suddenly had to become CEO, he found this role to be “against intuition.”
The following are the three mistakes that Chesky claims to have made:
1. Obey more experienced executives and delegate decisions.
Chesky said that, as CEO, he is often advised to hire highly experienced executives and then not to interfere too much with them.
He said that later he realized that this approach might not necessarily be the best for a young company: “You have to hire people who are just a bit more advanced, smarter, and more motivated than you, and you must maintain a very close collaboration with them.”
Chesky indicates that he also often ignores his own intuition and instead listens to those executives who have much more experience than him and are usually much older as well.
“For me, the hardest part is that sometimes my intuition tells me one thing, while they tell me another. What should I do when my intuition conflicts with their experience? Usually I end up giving in, and that’s often a mistake,” says Chesky.
He said that executives from much larger companies often find it difficult to apply the practices that are effective in those large companies to the needs of small startups.
“They also come from companies that were not created by them themselves. What they manage are existing companies. And now they must build them from the ground up,” said Chesky.
2. Overly trying to please others
Chesky said that when a colleague's work does not meet the requirements, he finds it very difficult to hold them accountable.
He said that he has always struggled with knowing "when to tell others what to do," and it is also difficult for him to have tough conversations about employees' performance. He mentioned that he "avoids conflicts to such an extent that if someone is not suitable for the job, I won't take any action."
“I’m cautious about becoming a boss,” said Chesky, “I feel like I kind of need to please others. I hope people like me.”
He said that sometimes he would take over the work of his employees himself, without realizing that doing so might either not give them enough room to succeed or be a unsustainable way of covering for their mistakes.
3. Not saying "no" often enough
Chesky said that another mistake he made was not saying "no" often enough, which led to a lack of clear focus within the company.
He compared the situation where executives each pursue different priorities to passengers in a car who all want to go to different places.
"There is only one correct way. And that way must be your way," said Chesky.
He said that if a senior executive leads the team in a direction that CEO does not agree with, then even if this person leaves later, the company may still have to bear the consequences for a long time.
“They’ve been following that path for two years now. What will happen next? They’ve gone down that road. It might take you five or ten years to fix or correct the decisions that person made back then,” said Chesky.
This article is reported by journalist Amanda Goh from Business Insider.
