Brian Chesky’s new playbook

Takeaways

Everyone Must Row in the Same Direction
Clarity beats compromise. Instead of negotiating how to run Airbnb, Brian made a clear call: unify under one roadmap, one set of priorities, and one way of working. Less micromanagement. More detail. Everyone moving together.

In the Details Is Where Leadership Lives
Brian rejects the stigma around micromanagement. He distinguishes it from “being in the details,” which he says is a sign of true leadership. You can’t lead if you don’t understand the work. You can’t evaluate performance if you don’t know what’s being built.

Rebuilt Product Management from First Principles
Airbnb didn’t eliminate product managers. It redefined them. Chesky merged product marketing with product management, offloaded program management, and kept only senior talent. Now, PMs influence instead of control. They shape the story and bring design, engineering, and marketing into one conversation.

Function Over Division
The old divisional model created politics, dependencies, and bloat. Airbnb moved to a functional structure—design, engineering, writing, marketing—mirroring a startup. Every function reports to a domain expert. Less redundancy. More speed.

Rolling Roadmap, Two Releases Per Year
No annual planning. Airbnb runs on a rolling 2-year roadmap, updated every 6 months. They release major features every May and November. Each release is a chapter in a longer story. The roadmap dictates the calendar—not the other way around.

Performance Marketing ≠ Product Growth
They pulled back on paid growth. Performance marketing works like a laser—precise but limited. Airbnb’s new playbook is simple: build something great, tell people about it, and let the product grow itself.

Guest Favorites: Reliability Meets Delight
Airbnb’s winter release introduced “Guest Favorites”—a curated collection of top-rated homes. Powered by AI and 370M+ reviews, it solves Airbnb’s biggest weakness: reliability. The goal is to offer hotel-like consistency without losing uniqueness.

Smaller Teams, Fewer Projects, Faster Execution
Airbnb trimmed the number of projects, reduced layers of management, and shrank teams. One team does one thing well. More people = slower work. A thousand people working like ten is the goal.

Culture Shift: Shared Consciousness, Constant Reviews
Chesky introduced weekly-to-quarterly reviews, run with a program manager scoring every project green, yellow, or red. These reviews aren’t just check-ins—they dictate the tempo. Progress is visible, obstacles are surfaced fast, and accountability is unavoidable.

How Brian Avoids Burnout
Surprisingly, being more involved gives him more time. Less rework. Fewer surprises. He avoids overworking by stepping away, prioritising workouts, eating clean, and staying close to old friends and family. Health, work, and relationships stay in balance.

Always Be Learning (Like a Child)
Brian stays sharp by staying curious. He still feels like a beginner. He reaches out for help without shame, reads constantly, and learns by teaching others. The goal isn’t to arrive—it’s to stay in a state of becoming.

Add a Zero: Push the Team to Think 10x
His leadership philosophy: set goals that feel too big. Not because they’re meant to be hit every time, but because they force first-principle thinking. Big goals change how teams think, not just what they do.

From Artist to CEO: How Design Shaped Airbnb
Before Airbnb, Chesky was a designer. RISD-trained. Obsessed with form, structure, and human experience. That design lens still shapes how Airbnb works—blending art, logic, and storytelling into everything they build.

Top Quotes

💬 There's this negative term called micromanagement. I think there's a difference between micromanagement, which is like telling people exactly what to do, and being in the details. Being in the details is what every responsible company's board does to the CEO.

💬 The story will often dictate the product because ultimately you have to tell the story to people, but a story also is a really helpful way to develop a cohesive product.

💬 The less involved I was in the project, the more spin there was, the less clear the goals, the less advocacy the team had, the fewer resources they had, and then, therefore, the slower they moved

💬 We're not going to have divisional leaders. We're going to have design, engineering, product marketing, marketing, communications, sales, and operations— all the functions of a startup.

💬 If you're a founder, what I would tell you is the problem with finding a negotiation between how you want to run a company and the people you want, is that's a good way to make everyone miserable.

💬 The role of a leader is to see potential in people that they may not even see themselves.

💬 To create a great guest experience, you need great hosts. And to have great hosts, you need great tools.

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