Chip Conley

The most effective way to find and learn from mentors is to admit what you don't know, regardless of your seniority.

"Brian would go to experts and say to the expert, 'I don't know what the hell I'm doing.' He did that with me when it came to hospitality. I appreciated that a guy who had a lot of hubris... could also..."

Mentorship is less about giving answers and more about providing the confidence and questions that help a mentee find their own path.

"Maybe that's what a mentor can be is a confidant, someone who gives you confidence and helps by asking questions, helps you as the younger mentee find your roadmap to success."

Modern mentorship should be intergenerational and reciprocal, where both parties exchange different types of knowledge (e.g., technical vs. management).

"One of the things I loved at Airbnb... where I had something to teach them and they had something to teach me... mutual mentorships."

When transitioning roles, focus your resume on problem-solving narratives rather than just job titles.

"What I love to see is not so much what roles you've had... Give me, in a paragraph, a thorny problem you faced. What was the problem, and what skills you used to actually accomplish it, and what was t..."

A successful career transition requires a mindset shift where the candidate evaluates the company's culture as rigorously as the company evaluates them.

"When you're interviewing, you're also interviewing them. When you're interviewing, it's not about you having to prove yourself. It's also for them to actually prove themselves as a company."

Alignment is often achieved through 'process knowledge'—understanding the underlying motivations of different departments to navigate the org chart.

"Process knowledge allows you to understand, how do you deal with an org chart and get things done partly because you understand the motivations of different groups?"

In the AI era, generalists who can think broadly and solve diverse problems are becoming more valuable than narrow specialists.

"We are moving out of the era of the specialists and into the era of the generalists... I would also say, are they a generalist when they're a problem solver?"

Evaluating a company's culture during an interview requires asking pointed questions about endemic problems and alignment.

"What are three to five adjectives that define this culture? What's the biggest problem in this culture... Is it ever going to get fixed? How could I come in and maybe help that?"

Culture serves as a decentralized decision-making guide, especially in remote or distributed teams.

"Culture is what happens around here when the boss is not around. The more distributed a company, the more culture is important."

Focusing on 'culture add' rather than 'culture fit' promotes diversity and prevents the exclusion of 'aberration' candidates.

"I like to say culture add, because culture fit to me can actually be quite negative toward somebody who is the aberration... A culture add suggests that actually having some diversity on the team is h..."

Employee satisfaction is a hierarchy where meaning and recognition differentiate great cultures from those focused solely on compensation.

"The employee model is really simple. It's money or compensation at the base, recognition in the middle, and meaning at the top."

Founders often assume employees share their extreme work pace, requiring boundaries and clear communication.

"Brian assumed everybody else was going to work at the same pace and duration... His point of view is like, 'Hey, we're having a meeting in the office tonight at 10 o'clock. Be there.'"

Managing up effectively requires balancing your own expertise with humility when reporting to a younger or less experienced leader.

"I was mentoring Brian on leadership, but he was also my boss... It required me to have a certain amount of humility as well as to be reporting to a guy 21 years younger than me, Brian."

Start meetings with high-intensity founders by explicitly aligning on intentions and success metrics to prevent the session from going off-track.

"I would say, 'Lenny, let's do a little pep talk, you and me before the meeting.' I want you to start the meeting with the following as you present and Brian's in the room. 'Brian, let's talk about wha..."

When dealing with unpredictable founders, use minimal slide decks to maintain flexibility in the conversation.

"I always wanted to really limit the deck as much as possible, because I didn't know where the meeting was going to go. I wanted the decks helpful at the start, at the very start, to just set principle..."

Anxiety in uncertain environments can be managed by breaking it down into what is known vs. unknown and controllable vs. uncontrollable.

"Anxiety equals uncertainty times powerlessness... 98% of anxiety comes from two sources. One is what you don't know, and number two is what you can't control or influence."

A powerful product vision moves beyond the functional 'what' (home sharing) to the emotional 'why' (belonging).

"Ultimately, we came up with the idea that we were in the belong anywhere business. Airbnb was not in home sharing, we were in belonging anywhere."

True product innovation comes from identifying and meeting the needs customers haven't yet articulated.

"The customer pyramid, briefly... is meeting expectations is the base, meeting desires is in the middle, and then meeting unrecognized needs."

Setting 'ridiculous' or impossible goals can be demotivating and stressful if not balanced with emotional intelligence.

"Brian had that he had to maybe create ridiculous goals, because even if we hit half of that goal, it was very encouraging. What he missed in that was the fact that when you miss a goal... you're setti..."

In tech, the 'product' is often the digital interface and platform, but for the user, the product is the real-world experience.

"Isn't the product the homes and the apartments? Jobot said, 'Nope. Product in the tech industry is something different.'"

User research must include diverse demographic segments to prevent biased product decisions (like going mobile-only).

"I just said, 'Listen, let's get some older people who are hosts in here to see how well they will be versed in managing their listing purely on mobile.'"

Direct, in-person observation of customers in their own environment provides credibility that data alone cannot offer.

"I actually went into the homes of these hosts all around the world... I think I was lucky because Brian did less of that than he did with other people."