Brian Chesky at Config 2023: 8 Lessons For Product Designers

Brian Chesky is an industrial designer mostly known for co-founding and being the CEO of an American San Francisco-based company operating an online marketplace for short- and long-term homestays and experiences, Airbnb.

Founded in 2008 by Brian Chesky, Joe Gebbia, and Nathan Blecharczyk, Airbnb revolutionized the way people travel and find accommodations around the world. Airbnb has become synonymous with design-led thinking, leveraging the power of creativity to redefine the hospitality industry.

Chesky’s passion for design and unique approach to running a company garnered attention and admiration from designers and aspiring entrepreneurs. His deep understanding of the impact that design can have on every aspect of a business enabled Airbnb to transcend its near-collapse, reclaiming 80% of lost business and generating a remarkable $4 billion in free cash flow.

At a recent conversation with the CEO of Figma, Chesky offered valuable insights into his philosophy of running a design-led company. During Config 2023, an industry event, he shared his lessons on replacing traditional product roles, the power of hypothesis-driven strategies, and the genius approaches that have shaped Airbnb's success story through a design lens. 

Many companies nowadays treat design just as a service, while Chesky as a designer has a profound understanding of that field that allows him to build a design-led company that continues to push boundaries, challenge conventions, and create unforgettable experiences for millions of travelers. And here you can read more about the importance of design that helps Airbnb scale its business and build culture.

What’s profound about Chesky conversation with the CEO of Figma, Dylan Field, is the wide perspective on design that goes beyond the narrow and simple view of the design as a service.

1. Background

Brian Chesky, during the conversation at Config 2023, shared that he realized he was doing things in a very conventional way, despite his design background, which led to many problems and stagnation in Airbnb’s growth.

“I started noticing the more people we added, the more project we pursue, the less our app changed, and the more cost went up. And I don’t know what to do.“

The co-founder of Airbnb decided to enlist the help of two legendary designers associated with Apple, Hiroki Asai and Jony Ive. The first was Apple's creative director from 1998 to 2016, while Jon was in charge of design and was responsible for designing devices such as the iPhone or MacBook. Here you can read more about Johny Ive’s powerful philosophy and principles behind his designs.

After the conversion with Jony Ive and Hiroki Asai, Chesky remembered the magical Renaissance of Steve Jobs' era at Apple. They described how design stood at the core of that remarkable period in Apple's history. The CEO of Airbnb realized:

“It was totally different way of running a company than everything I was taught“

Then, Chesky hired Hiroki, and became the biggest client for Ive’s design studio. The co-founder embraced his newfound designer spirit and unconventional thinking by boldly expressing:

“I realized that for 10 years I was apologizing for how I wanted to run the company as a designer but I just didn’t have the nerve“

Their mission was to figure out how to run the company better by placing design at its very core.

2. Principles

Brian Chesky is the only CEO designer in Fortune 500. At Config 2023, he shared lessons on how he rebuilt the company from the ground up and how pushing design-driven strategies allowed Airbnb to go from a simple business unit organization to a functional organization.

“There are two types of people that never become CEOs. Designers and heads of HR never become CEOs. And I think it’s because design in some way is fragile. Companies are organized around scientific method and the creative process is something that requires nerve.“

Elon Musk once said that all managers in a technical area must be technically excellent. Chesky agreed, saying that this rule applies to the design as well. In his opinion, design leaders should be highly technical and spend a large amount of their time designing and reviewing work.

So, here are the lessons for all the designers who want to level up their expertise and get a deeper understanding of product, design, and operating company.

1) Design is much more than a department. It’s a way of thinking about the world.

"Design is much more than a department. It’s a way of thinking about the world. And I think there’s a whole new generation of designers that aren’t just going to work for engineers. They’re going to sit alongside engineers. They’re not just going to be told what to do by product managers. They are going to help drive the product. And some of them are going to choose to drive companies. Because ultimately what everyone wants is to have a product people love."

Design is much more than just moving pixels around, for example, a designer can design not only a user interface but also a company to have fewer parts, how people work, or a vision behind the company.

2) Simplifying is not about removing things but distilling them to their essence. And this requires a profound understanding of a product. 

“Designers should be trying to simplify every single thing they do. And I was thinking that simplifying was removing things. It’s distilling something to its essence. And to simplify, you have to deeply understand it. It’s physics. It’s first principles. And I think there has to be a sense of craft. Obsessing over every single detail.“

The power lies in simplicity.

3) Designers should only ship things they’re proud of. Airbnb focuses on shipping things that they're proud of.

“[Designers] only should ship that you’re proud of. Don’t test something until after you’re happy. Because artists, first and foremost, should make something for yourself, and when you love it, and you are proud of it, now you’re ready to put it out to somebody else.”

At Airbnb, the rule is simple: if you're not proud to put your name on your work, don't ship it.

4) When faced with a choice between two options, the right answer is often the third option - this needs creativity and a heart.

“You ever see like there are two bad options and you’re not trying to pick between two-bit options. Sometimes the right path is the third path. And that third path requires creativity. I think that a lot of business needs more heart and more imagination. And that is what everyone in this room can provide. So I would just encourage designers to have a nerve.”

Creativity is where designers excel.

5) If you are going to do an A/B test, it should be hypothesis-driven. If it works, you should be able to say why, not just what.

“We not going to do A/B testing unless you have a hypothesis that B is better than A and you can tell why you think that way.“

Have a hypothesis and think by the first principle.

6) Engineering and Product Management should be paired with Design from early on

“I would like to often tell engineers, the best thing for you is to pair you with design. Because otherwise it’s like running and one of your legs is shorter than the other. You’re not going to go very fast. And the best thing for engineers and the best thing for PMs is to pair them with great design from the beginning. Because a lot of companies’ design has become service organization. Design should not be a service organization unless that is explicitly the intention of the CEO.“

Design challenges technology and technology inspires art.

7) Design is not just a service

“Designers should not be just focused on services, they should be focused on user flows“

By understanding the intricacies of user journeys, designers can create intuitive and efficient interactions that elevate the product.

8) Combine data and research to get the best user experience

“Combine data and research, they are equally important. And research means not only users but historical references. I think being a designer is like holding 5,000 ideas in your head, some of them contradictory, and we tend to call this intuition and we get really nervous. Because it seems somehow not systematic. But I actually think a lot of great design comes from a deep understanding of a problem. And so you’re trying to absorb as much information as possible.”

When Airbnb made Airbnb Rooms, they designed an animation that reminds the opening of a passport to make people familiar by giving them a point of reference, so they better understand the product.

Additionally, Brian sees designers very much as architects and made them equal to product managers. He got rid of the classic product management function. And what’s interesting Apple didn’t have it either.

“Who’s the product manager when you designing a building? The architect“

At the end of the conversation, the co-founder of Airbnb shared his advice on how to start something and how a profound understanding of design allows you to possess the most important skill in the 21st century:

“I think of myself maybe as a designer, but I’m not a designer the way most of you are. But I designed a business model. I designed our expense base. I helped designed an organizational chart. Our business. How we work. Our story. I think that design is not just how something looks, it’s how it fundamentally works. And I think it is one of the most important skills that we’re going to need in the 21st century.”

Steve Jobs once said that the most powerful person is the storyteller and it seems that Brian took his words to heart because the way he was talking about making Airbnb a design-led company by simple analogies and clear messages struck me. And if you learn more about mastering the art of storytelling, read my previous article on that topic.

Summary

“Just know that designers can run companies, they can build things, they can ship things, and ultimately make something people want. Well, who knows what people want as well as designers? Not many other people. I think that is a core value that we have to the world and I just think more designers should rise up and start companies.”

Finally, it is worth mentioning that according to Chesky, designers should be more courageous in talking about things and creating an opportunity to discuss the product. If you're in charge of a design team, make sure that the whole company is embracing your philosophy or at least willing to have a conversation about it.

If you find it interesting, get in touch with me on Twitter!

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