4 things an executive learned from reporting to Airbnb CEO Brian Chesky

Vlad Loktev previously reported to Airbnb CEO Brian Chesky before becoming a VC. He says he learned a lot from his time under Chesky.

During his decade at Airbnb, Vlad Loktev picked up some pointers from CEO Brian Chesky.

Loktev, who previously was a senior product manager at Zynga before joining Airbnb, rose from a growth PM to ultimately managing over a thousand people within design, engineering, and other operations while reporting directly to Chesky as a VP and GM.

Though he eventually left in 2022 and is now a partner at Index Ventures, Loktev revealed in a new episode of “Lenny’s Podcast” four things he learned from Chesky as one of his “most trusted partners.”

Embrace the chaos

Although chaos in the workplace usually reads as scary to most people, Loktev said that it “is actually great.”

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

He recalled Chesky telling him, “Hey, I just don’t feel good. Something feels off.” Although Loketev noted that their booking numbers were up and things appeared to be running smoothly, the CEO responded, “Things are just too calm. I don’t like it.”

He then picked an important project that was scheduled for a multi-week design process and building timeline.

“He said, ‘Yeah, I don’t care about any of that. We’re going to design this in 24 hours,'” Loktev said. “And I was just mind blown.”

Despite the eruption of the neat time flow originally planned, they did manage to complete the design in a little over a day. Loktev said he learned from how Chesky strategically inserted some disarray into an otherwise calm process.

“That chaos forced us, with our artificial time constraint, to dial up our intuition and to think a bit more creatively than maybe we would have in the past,” he said.

How to continue growing

After starting as a product manager, Loktev held several roles during his decade at Airbnb, from director of product to VP and GM of Airbnb Plus.

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

He said that as soon as he got comfortable in a position, everything familiar would “break.” From different projects and hiring processes to how he would spend his time, Loktev said he would have to “reinvent” himself in each new development.

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

And he learned it from Chesky, whom Lokteve said would continuously grow.

“Every six months, it was like a different person,” he said. “And a lot of his secret sauce is not being afraid to ask people for help who are experts in the thing that you’re trying to learn.”

“My motto is, “Ask for the impossible, and sometimes you’re going to be surprised,” he added.”

Top-down leadership

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

“That’s not actually a reality of top-down,” Loketev said. “In that room where we made many of the hard decisions with Brian, the reality was he asked a shit ton of questions.”

The former VP said Chesky would refrain from immediately advocating for his own opinions but rather would listen and often change his mind as a result.

“So as a leader at Airbnb for so long, I never felt like I wasn’t listened to or like he was just making these random decisions,” he said. “I always had an ability to influence and an ability to voice where I felt like the company should go.”

Chesky’s involved approach has even inspired recent critique around Silicon Valley’s modus operandi of “manager mode,” when startups scale up and their founders tend to delegate tasks and create distinct administrative tiers that isolate them from everyone but their direct reports. Paul Graham, the founding partner of the startup accelerator Y Combinator, credited Chesky in his blog post about the alternative, “founder mode” — or being highly hands-on across the company.

“The less hands-on I became, the more I got sucked into problems,” Chesky once said in a podcast. “And by the time I got sucked into a problem, it was like 10 times as much work.”

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

Chesky has said he decided to follow Steve Jobs’ approach of not letting Apple do more than he could focus on.

“We’re going to be totally integrated — one road map,” he said. “I’m gonna do very few things, and I’m going to be involved in every single detail.”

And team members were able to feel his involvement, as well as their own. Loketev said that though Chesky made many decisions, “he was informed in those decisions.”

He added, “Many of us were contributing to all the information he needed to make the decision.”

It’s not about hitting the goal

When it came to thinking big, Loketev said Chesky taught him how to rethink big goals.

He said that workers tend to become intimidated by how they’ll be able to achieve these ambitious objectives — and the consequences if they cannot.

“The reality is, it’s not about hitting the goal, it’s about thinking how to hit the goal, and going through that creative journey of, what does the world need to look like for this crazy goal to be true?” he said.

Lokotev said that these massive targets can push people to consider the extremes of different possibilities — if everyone operates a certain way or if nobody does.

“Usually, it’s when you start testing the extremes that you begin to realize, ‘This is the path that we should actually take,'” he said.