Why 'Best Practices' Are Killing Your Business: Lessons I Learned Observing Brian Chesky

Repurposing conventional PMs and making them Product marketing managers or program managers.

Brian had tried every product org framework until a lightbulb lit one day.

Picture this: It's the end of 2019, and Brian is sitting in his office, staring at a wall plastered with 150 different screens that users interact with on Airbnb. He's got a nagging feeling that something's off. Here's a guy who's a designer at heart, but his company is operating like any other tech behemoth.

Then, inspiration strikes. Brian recalls how Walt Disney storyboarded the entire Snow White movie to keep track of its complex narrative. What if Airbnb had its own "storyboard"? What if they could map out the entire guest and host experience, from start to finish, and align every department around that vision?

Fast forward to the chaos of 2020. COVID-19 hits, and Airbnb loses 80% of its business in just eight weeks. Talk about a gut punch, right? But instead of panicking, Brian sees this as a crucible moment. It's time to rebuild Airbnb, but this time as a designer would.

He scraps the old structure and introduces a functional organization. Marketing, engineering, and design are no longer silos; they're interwoven threads in the fabric of Airbnb's new roadmap. And speaking of roadmaps, Brian becomes the keeper of a single, unified roadmap that he updates every week. No more sub-teams with sub-goals. It's one vision, one mission.

But here's the kicker: Brian doesn't just want to make things look pretty. He wants to make them work beautifully. He introduces design principles that are hypothesis-driven, focused on user flows, and obsessed with simplicity. He even redefines the role of A/B testing, making it a tool for validation, not a crutch for decision-making.

The result? Airbnb emerged from the crisis stronger, more focused, and more aligned than ever before. And it all started with a designer's intuition and a storyboard.

So, what's the lesson here? Never underestimate the power of design thinking. It's not just about how things look; it's about how they work, how they make people feel, and how they fulfill a vision. And sometimes, you have to tear down the old to build something truly extraordinary.

TL;DR

💡 Run the business/org/team however you want based on your circumstances 💡

👉 Best practices are dumb, have no governing body, and are no different than fashion trends. Coming and going from the latest gurus "how to work" book.

Brian said he's "tried everything", I imagine he means best practices, and they didn't work. Why? Because it's not playing Airbnb's strengths. As soon as he leaned into his strengths as a great design thinker, and the taste he brings to the table, that unlocked a pretty amazing performance culture.

👉 All rules are made up, and rules impact culture, if you don't design your own rules, and instead prescribe "best practices" then you don't care nor believe in the power of a good culture.

"Best practices" as an argument for doing something is lazy leadership, and therefore top-heavy management, leading to a vanilla culture. Nobody likes working somewhere that's vanilla.

👉 The rules you design should be based on the team you have on the bus, the hard thing about hard things is that as a leader, you need to evaluate your roster and actually make calls on their responsibilities based on their strengths.

Notice that Brian didn't say anything to the effect of "This is how every company should work". And we shouldn't interpret it that way. Airbnb's model works because of Brian's strong visionary leadership, not because it's the only way to do things.

If you are a PM listening to his talk, I imagine it makes you uncomfortable. If so, don't work for Airbnb, work for Amazon who is definitely not going to work like Airbnb.

This leads to my final insight:

💡It's your career, if you disagree with Airbnb, then don't work there. Work somewhere that has a culture that you align with. Work the way you want to work for people you align with. 💡

For me, and my preferences, I love where Airbnb's going. Why? Because it's my career.

Until next time,

Caden Damiano

P.S. If you're feeling stuck in the "conventional" way of doing things, maybe it's time to grab a pen and start storyboarding your own vision. You never know where it might lead you.

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