Brian Chesky on Hiring

Co-founder & CEO at Airbnb

17 insights8 categories

Co-founder and CEO of Airbnb who personally conducted interviews for the company's first 300 employees. Famous for spending months finding the right person for a role rather than settling, and for asking candidates whether they would take the job if they had only one year left to live.

“You have to hire like your life depends on it. In the early days of a startup, it does. Every single person you bring in is going to define the culture. They're not joining the culture. They are the culture.”

Brian Chesky personally interviewed the first 300 Airbnb employees. It took five months to hire the company's first engineer. People thought he was crazy. But Chesky understood something that most founders learn too late: your first hires are not joining the culture. They are the culture.

"Every single person you bring in is going to define the culture. They're not joining it. They are it."

His most famous interview question sounds extreme: "If you had one year left to live, would you take this job?" But the purpose is practical. It cuts through the polished answers and reveals whether someone is genuinely passionate about the mission or just looking for a paycheck. Chesky wants missionaries, not mercenaries, and he is willing to wait months to find them.

"I would rather have a role open for six months than fill it with the wrong person."

Every Airbnb candidate goes through a dedicated core values interview that is completely separate from the skills assessment. A values mismatch is an automatic rejection, regardless of technical ability. The values interview carries equal weight to everything else, and that is non-negotiable. Chesky learned from Steve Jobs that your first ten employees become your next hundred. They recruit, train, and mentor the next wave. If those first ten are exceptional, the ripple effect is enormous.

"Your first ten employees become your next hundred. If those first ten are exceptional, the next hundred will be too. If they're mediocre, you've locked in mediocrity."

The standard Chesky applies to every hire: would this person be in the top ten people you have ever worked with? If the answer is not clearly yes, he keeps looking.

Philosophy

Core beliefs about hiring and talent

Chesky believes the first hires define the DNA of the entire company. He personally interviewed Airbnb's first 300 employees and spent as long as six months filling a single role. His standard: would this person be in the top ten people you have ever worked with? If not, keep looking.

You have to hire like your life depends on it. In the early days of a startup, it does. Every single person you bring in is going to define the culture. They're not joining the culture. They are the culture.

Chesky personally interviewed the first 300 Airbnb employees. He saw each hire as a permanent cultural decision.

I would rather have a role open for six months than fill it with the wrong person. It took us five months to hire our first engineer. People thought we were crazy. But that person set the bar for every engineer who came after.

Airbnb's first engineer hire took five months of searching. Chesky considered it one of the most important decisions the company ever made.

Your first ten employees become your next hundred. They don't just do the work. They recruit and train and mentor the next wave. If those first ten are exceptional, the next hundred will be too. If they're mediocre, you've locked in mediocrity.

Chesky learned this from Steve Jobs and has repeated it in multiple interviews.

Hiring Process

How they structure interviews and evaluations

Airbnb's hiring process includes a dedicated core values interview that is separate from the skills assessment. Every candidate must pass both. The values interview carries equal weight to technical ability, and a values mismatch is an automatic rejection regardless of skill level.

Every Airbnb candidate goes through a dedicated core values interview that is separate from skills assessment. A values mismatch is an automatic rejection regardless of how technically skilled the candidate is.

The core values interview carries equal weight to the technical evaluation. This is non-negotiable at Airbnb.

In the early days, Chesky personally interviewed every candidate. As Airbnb grew, he transitioned to reviewing every offer. He stayed involved in hiring decisions far longer than most CEOs would.

Interview Questions

Questions they ask candidates

Chesky's most famous interview question asks candidates whether they would take the job if they had one year left to live. It sounds dramatic, but the purpose is practical: it reveals whether someone is genuinely passionate about the mission or just looking for a paycheck.

If you had one year left to live, would you take this job?

Chesky's most famous question. It sounds extreme, but it cuts through the noise. If the answer is yes, that person is genuinely passionate about the mission. If they hesitate, they are probably looking for a paycheck, not a calling.

Why Airbnb? What is it about this company specifically that makes you want to be here?

Chesky uses this to distinguish missionaries from mercenaries. He is listening for genuine connection to the mission, not generic enthusiasm about the brand.

Tell me about a time you did something that everyone around you thought was impossible or a bad idea. What happened?

Tests founder mentality. Chesky wants people who have the conviction to push through resistance when they believe in something.

What They Look For

Traits and signals that excite them

Chesky looks for missionaries who genuinely believe in the company's mission, people who bring a founder's mentality to their work, and candidates who would be in the top ten people you have ever worked with.

Missionaries who genuinely believe in the mission. People who light up when talking about what Airbnb is trying to do, who see the work as a calling rather than a career move.

Candidates who would be in the top ten people you have ever worked with. Chesky applies this bar to every hire and encourages his team to do the same.

Founder mentality. People who take ownership of problems beyond their job description, who treat the company's problems as their own problems.

Dealbreakers

Warning signs that concern them

Anyone who treats the job as just a job, who is primarily motivated by compensation, or who cannot articulate genuine passion for the mission. Chesky has zero tolerance for culture dilution in early hires.

Anyone who treats the job as just a job. If a candidate's motivation is primarily compensation, title, or brand prestige rather than genuine passion for the mission, they will dilute the culture.

People who cannot articulate why Airbnb specifically. Generic answers about 'great company' or 'cool product' signal a lack of genuine connection to the mission.

Signals to Watch

Subtle cues they pay attention to

Chesky watches for whether candidates light up when talking about the mission. The emotional response to 'Why Airbnb?' reveals everything about whether someone will bring founder-level intensity or clock-in-clock-out energy.

Whether candidates light up when talking about the mission. The emotional response to 'Why Airbnb?' is nearly impossible to fake and reveals whether someone will bring founder-level intensity or clock-in-clock-out energy.

Frameworks

Mental models and structured approaches

Chesky's core framework: your first hires are not just employees, they are co-founders of the culture. Hire as if each person will clone themselves ten times, because culturally, that is exactly what happens.

Your first hires are not just employees. They are co-founders of the culture. Hire as if each person will clone themselves ten times, because culturally, that is exactly what happens. The standard they set becomes the standard for everyone who follows.

Interviewer Tips

Practical advice for running interviews

Never compromise on values fit for speed. The time you save by rushing a hire is nothing compared to the cultural damage of bringing in someone who does not share your core beliefs. It took Chesky five months to hire Airbnb's first engineer.

Never compromise on values fit for speed. The time you save by rushing a hire is nothing compared to the cultural damage of bringing in someone who does not share your core beliefs. Keep the role open until you find the right person.

Create a separate core values interview that carries equal weight to skills assessment. Make it non-negotiable. A candidate who passes the skills bar but fails the values bar is a net negative, no matter how talented they are.

Frequently Asked: Brian Chesky on Hiring

Interview questions Brian Chesky is known for asking candidates.

If you had one year left to live, would you take this job?+

Why Airbnb? What is it about this company specifically that makes you want to be here?+

Chesky uses this to distinguish missionaries from mercenaries. He is listening for genuine connection to the mission, not generic enthusiasm about the brand.

Tell me about a time you did something that everyone around you thought was impossible or a bad idea. What happened?+

Tests founder mentality. Chesky wants people who have the conviction to push through resistance when they believe in something.

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