4 Things This CEO Learned From Airbnb CEO Brian Chesky

Embrace the chaos

While workplace chaos typically strikes most people as terrifying, Loktev said it “actually feels great.”

“Sometimes you want to create chaos in an organization to force them to think creatively and actually make leaps in product development,” he said.

He recalled Chesky telling him, “Hey, I just don’t feel right. Something’s wrong.” Although Loketev noted that their bookings were up and things seemed to be going smoothly, the CEO responded, “It’s just too quiet. I don’t like it.”

He then selected an important project whose design and implementation process would take many weeks.

“He said, ‘Yeah, I don’t care. We’ll design it in 24 hours,’” Loktev said. “And I was just blown away.”

Despite the disruption to the originally planned, tidy flow of time, they managed to complete the project in just over a day. Loktev said he learned from Chesky strategically introducing a bit of chaos into the otherwise calm process.

“This chaos forced us, under an artificial time constraint, to sharpen our intuition and think a little more creatively than we had in the past,” he said.

How to continue developing

Starting as a product manager, Loktev held several positions over his ten years at Airbnb, from chief product officer to vice president and general manager of Airbnb Plus.

“The truth is that every three to six months my job changed,” Loktev said.

He said that once he gets comfortable in a position, everything familiar “will crack.” From different projects and hiring processes to how he spends his time, Loktev said he will have to “reinvent himself” with each new development.

“One thing I’ve learned is that you have to ask for help,” he said. “It takes a village, right? You can’t get there alone.”

He learned this from Chesky, who according to Lokteve was expected to continually improve.

“It was a different person every six months,” he said. “And a lot of his secret sauce is that he’s not afraid to ask for help from experts in the field he’s trying to learn.”

“My motto is: ‘Ask for the impossible and sometimes you will be surprised,’” he added.

Top-down leadership

The negative connotations of top-down leadership can often conjure up an image of a leader making all the decisions “in an ivory tower” while everyone else sits powerless below. Loketev said that — at least at Airbnb — this is a common misconception about top-down organizational structures.

“It’s not really a top-down reality,” Loketev said. “In that room where we were making a lot of tough decisions with Brian, the reality was that he was asking a hell of a lot of questions.”

The former vice president said Chesky refrained from immediately pushing his own views, but instead listened and often changed his mind.

“As the leader of Airbnb for so long, I never felt like I wasn’t being listened to or that I was making these random decisions,” he said. “I always had the ability to influence and articulate where I thought the company should go.”

Chesky’s hands-on approach has recently drawn criticism of a Silicon Valley modus operandi known as “manager mode,” in which startups grow while their founders delegate tasks and create separate layers of management that isolate them from everyone but the people they directly report to. Paul Grahamthis founding partner of the startup accelerator Y Combinatorattributes to Chesky in his blog post about the alternative “founder mode” – that is, very practical involvement in the company’s affairs.

“The less hands-on I was, the more I got into problems,” Chesky once said on a podcast. “And once I got into a problem, it was about 10 times more work.”

Graham said that instead of running startups like managers, founders should adopt “founder mode” and get even more involved.

Chesky said he decided to follow in Steve Jobs’ footsteps and not let Apple do more than he was capable of doing.

“We will be completely integrated — one road map,” he said. “I will do very few things and I will be involved in every detail.”

And the team members could feel his commitment, as well as their own. Loketev said that although Chesky made many decisions, “he was aware of those decisions.”

He added: “A lot of us contributed all the information he needed to make a decision.”

It’s not about hitting the target

Loketev said that when it comes to thinking big, Chesky taught him how to think big.

He found that employees often feel intimidated by how they will achieve these ambitious goals — and the consequences if they fail.

“The truth is, it’s not about achieving the goal, it’s about thinking about how to achieve the goal and going through this creative journey of what does the world have to look like for this crazy goal to be real?” he said.

Lokotev said these huge goals can force people to consider extreme options — whether everyone would act a certain way or no one would act at all.

“Usually when you start testing extremes, you start to realize this is the route we should actually take,” he said.