Discover Brian Chesky's unique leadership philosophy—from design thinking to founder mode—that transformed Airbnb into a global hospitality empire through empathetic, hands-on management.
In the pantheon of modern business leaders, few figures have redefined entire industries whilst maintaining such an unconventional approach to leadership as Brian Chesky. The co-founder and CEO of Airbnb has crafted a leadership philosophy that reads like a masterclass in transformational management—one that bridges the gap between artistic sensibility and business acumen. Since 2007, Chesky has overseen Airbnb's growth from a humble air mattress rental service to a community of over 5 million hosts welcoming more than 2 billion guests across 240+ countries and regions. His approach challenges conventional management wisdom and offers a compelling blueprint for leading through uncertainty in an increasingly complex business landscape.
What distinguishes Chesky's leadership style from his Silicon Valley contemporaries? The answer lies in his unique synthesis of design thinking, empathetic decision-making, and what has recently been termed "founder mode"—a hands-on approach that prioritises deep product understanding over traditional delegation. Like a master craftsman who refuses to abandon his tools as his workshop grows, Chesky has maintained an intimate connection with the details of his business whilst scaling it to unprecedented heights.
Chesky's leadership philosophy finds its roots in an unlikely place for a tech CEO: the Rhode Island School of Design. A graduate with a Bachelor of Fine Arts in industrial design, Chesky was influenced by the works of Charles Eames, Ray Eames, and Walt Disney during his studies. This artistic foundation has become the cornerstone of his leadership approach, fundamentally shaping how he views problems, solutions, and the very nature of business itself.
The Designer's Lens in Business Strategy
Chesky brings a designer's point of view to the table, valuing creativity, innovation, and simplicity—all of which are evident in the intuitiveness of the platform and the branding of Airbnb. He firmly believes that good design is not just about looking good; it's about solving problems. This philosophy extends far beyond aesthetic considerations to encompass the very structure of his organisation.
During his keynote at Figma's Config 2023, Chesky posited that design is about creating aesthetically pleasing products and using creative and strategic thinking to solve complex problems. For Chesky, a designer's work extends beyond moving pixels; they are responsible for designing the company from within.
The practical manifestation of this design-centric approach can be seen in Airbnb's office culture. Chesky came up with the idea to design meeting rooms identically to the apartments of Airbnb users. All of their meeting rooms were modeled piece by piece after apartments on their website, recreating the actual rooms so that meeting spaces became homes you walk into. This seemingly quirky decision reflects a deeper understanding of how physical environments shape thinking and culture—a principle that would serve Chesky well during his company's most challenging periods.
In recent years, Chesky has become synonymous with the concept of "founder mode," though he's quick to clarify his perspective on this much-debated management philosophy. Chesky emphasised that he did not coin the term "founder mode" and prefers to focus on the mindset rather than the title. He believes that great leaders are in the details, stating: "The point is this: Great leaders are in the details. That's what founder mode is".
Rejecting Conventional Delegation Wisdom
Chesky's approach directly challenges the traditional management maxim of "hire great people and trust them to do their job." He described this philosophy as "terrible leadership," noting that visionary leaders like Steve Jobs, Walt Disney, and Elon Musk never subscribed to such hands-off approaches. Instead, Chesky advocates for what he calls "presence, not absence"—a leadership style that maintains intimate knowledge of operational details without descending into micromanagement.
His stance on employee autonomy is notably direct: "If you want to be autonomous, start your own company," Chesky has stated. This perspective reflects his belief that coherent vision and execution require centralized understanding and coordination, particularly in rapidly evolving markets.
The Steve Jobs Influence
Chesky has modeled his leadership style after Steve Jobs, who brought Apple from the brink of bankruptcy in 1997. He believes that "the CEO of the company should always be the chief product officer". This philosophy manifests in Chesky's deep involvement in product decisions and his insistence that leaders must understand their products better than anyone else in their organisation.
The parallel to Jobs extends beyond mere tactical approaches. Both leaders share a conviction that exceptional products emerge from coherent vision rather than distributed decision-making, and that the CEO's primary responsibility is to maintain the integrity of that vision through all levels of execution.
Perhaps no aspect of Chesky's leadership style has been more rigorously tested—or more clearly demonstrated—than his capacity for empathetic leadership. The COVID-19 pandemic presented an existential crisis for Airbnb, with travel restrictions causing the company to lose 80% of its business within eight weeks. Chesky's response during this period offers a masterclass in leading with both head and heart.
Crisis Leadership with Compassion
During the pandemic, Chesky had to make difficult decisions, including cutting 25% of Airbnb's workforce. However, he did so with transparency and compassion, addressing employees in a personal, emotional letter explaining the rationale whilst offering attractive severance packages. His approach earned respect even among those affected by the layoffs, demonstrating that empathetic leadership can coexist with difficult business decisions.
Chesky implemented a $250 million relief fund for hosts who were struggling financially, demonstrating that compassion can coexist with business acumen. This not only reinforced trust in the Airbnb brand but also solidified employee loyalty, proving that a people-first approach can lead to sustainable success.
Empathy as Competitive Advantage
Chesky's empathetic leadership style builds trust and loyalty not only within Airbnb but in the Airbnb Global Community as a whole. He considered the emotional outcomes of his decisions and thereby cultivated a respect-and-understand culture. This approach extends beyond crisis management to everyday operations, where Chesky's design background informs his understanding of user experience.
As Chesky explains: "I had to sit in the shoes of the child. And so I had to imagine being a child getting on the operating table. You had to put yourself in the shoes of the patient or the person using your product. If you're only doing A/B tests, you're never designing with empathy".
Central to Chesky's leadership philosophy is an almost missionary zeal for community building. This isn't merely corporate rhetoric—it represents a fundamental reimagining of what business can accomplish when it prioritises human connection over purely transactional relationships.
Mission-Driven Leadership
Chesky often stated that "Airbnb's mission would create a world where anyone can belong anywhere," and this is at the very core of their success. Under his leadership, values shine through in business decisions, guide employee actions, and set strategic priorities. This mission-driven approach has enabled Airbnb to weather regulatory challenges and competitive pressures by maintaining clear purpose.
The community focus extends to product development, where Chesky has championed initiatives that strengthen rather than merely monetise relationships. Take the case of Airbnb Experiences launched in 2016, which allowed users to book activities conducted by locals, giving them an authentic travel experience. Chesky often emphasized, "The best way to create value is to make people feel valued".
Building Tribe, Not Product
Chesky has always been about values and contributing to society. The original idea sought to solve a key problem—insufficient rent money—but simultaneously met a concurrent community need. Chesky continues to see himself in this role by striving to create a product that's both likable and sustainable.
This tribal approach to business building has implications far beyond customer satisfaction. It creates network effects that make competition more difficult whilst fostering the kind of evangelical customer base that traditional marketing struggles to achieve.
One of Chesky's most endearing and strategically valuable qualities is his commitment to continuous learning. Despite achieving extraordinary success, he maintains the intellectual humility of a perpetual student—a trait that has enabled him to navigate unprecedented challenges with grace.
Shameless Learning Philosophy
Chesky advised young leaders to be shameless when asking for help, noting that "you can't be afraid and feel as though you are bothering someone. Once you get to a certain level of success, you have the ability to meet and talk to anybody, so you should be shamelessly resourceful". This approach reflects a growth mindset that prioritises learning over ego protection.
When someone like Brian Chesky might seem beyond needing mentoring, he emphasizes how gaining knowledge from accomplished entrepreneurs remains vital. These early experiences taught Chesky about bold leadership through humility, enabling insights he wouldn't otherwise have gained.
Learning Through Direct Experience
Chesky's commitment to learning extends beyond seeking advice to immersing himself directly in customer experiences. Early on, Chesky famously became an Airbnb guest himself, staying in Airbnb rentals to understand the insider experience. This immersive approach helped him understand and improve the product whilst maintaining hands-on involvement with both hosts and guests.
During Airbnb's early days, Chesky and his co-founders literally knocked on the doors of all their hosts, saying, "Hello, this is Brian, Joe, we're founders, so we just want to meet you." These home visits became Airbnb's secret weapon for understanding what people loved about the service.
Chesky's approach to innovation challenges Silicon Valley's typical "move fast and break things" mentality. Instead, he advocates for what might be called "purposeful innovation"—a methodology that combines ambitious thinking with disciplined execution.
The 10X Rule and Transformational Thinking
Chesky famously uses the "10x rule," which challenges his team to think about how they can improve their offerings by tenfold rather than just making incremental changes. This philosophy has led to groundbreaking initiatives, such as the introduction of Airbnb Experiences, positioning Airbnb not just as a platform for accommodation but as a holistic travel experience.
This transformational approach to innovation reflects Chesky's design background, where breakthrough solutions often emerge from reframing problems rather than optimising existing approaches. The 10X rule forces teams to abandon incremental thinking in favour of fundamental reimagining.
Integrated Team Philosophy
During the pandemic crisis, Chesky advocated for creating products that resonated with their team's passion, stating: "You can't develop products if you can't talk about the products." This approach led to significant shifts in Airbnb's operational philosophy, resulting in record cash flow despite challenging circumstances.
The integration extends to organisational structure, where Chesky has moved away from traditional business unit silos toward functional departments that mirror startup operations even at scale. This structure supports his founder mode philosophy whilst maintaining the agility necessary for rapid innovation.
Not all aspects of Chesky's leadership style have escaped criticism. His public acknowledgment of having "favorites" within his organisation has sparked debate about fairness and team dynamics, yet his approach reveals sophisticated thinking about talent development and strategic execution.
Strategic Favoritism as Leadership Tool
Chesky argues that employee favoritism can spotlight high performers as an example to follow, utilize skill sets more efficiently, and use favored employees in strategic planning decisions. He invites up to 100 employees to biannual meetings where business decisions are made—and sometimes, the same people are invited repeatedly.
This approach challenges egalitarian assumptions about management, suggesting that transparent meritocracy might be more effective than false equality. However, experts warn that favoritism can create dissension within teams and establish unrealistic expectations, potentially leading to a toxic work culture where some individuals feel they matter less than others.
Balancing Individual Recognition with Team Cohesion
The favoritism controversy illuminates a fundamental tension in modern leadership: how to recognise and leverage exceptional talent whilst maintaining team cohesion. Chesky's approach suggests that transparency about differential treatment might be preferable to pretending all contributions are equal, though this requires careful implementation to avoid demoralising team members.
The COVID-19 pandemic represented perhaps the greatest test of Chesky's leadership philosophy, forcing him to apply his principles under existential pressure. His response during this period offers valuable insights into how design thinking, empathy, and founder mode principles function during crisis.
Psychology of Crisis Management
As Chesky reflects: "The hardest thing to manage in a crisis is your own psychology. People look in your eyes, and if you think you're screwed, they see it in your eyes. You need to be optimistic. But it can't be optimism that's delusional. The optimistic mentality is the mentality you need to be creative. And you need to be creative because, in a crisis, you often have no good solutions".
This insight reveals the psychological sophistication underlying Chesky's leadership approach. He understands that leader's emotional state cascades throughout the organisation, making emotional regulation a strategic imperative rather than merely personal development.
Opportunity Within Crisis
Chesky viewed the crisis as an opportunity to restore Airbnb's focus on what mattered. He scaled back ambitious projects and shifted resources to reinforce Airbnb's core business, offering homes to guests. The reflective pivot allowed Airbnb to recover sooner than most competitors.
Rather than simply weathering the storm, Chesky used the crisis to strip away non-essential activities and refocus on core value propositions. This disciplined approach to crisis management reflects his design thinking background, where constraints often generate better solutions than unlimited resources.
Chesky's leadership philosophy extends beyond quarterly results to encompass what he calls "building for 100 years." This long-term perspective influences everything from product development to cultural decisions, setting Airbnb apart in an industry often criticised for short-term thinking.
Century-Scale Thinking
One of the cornerstones of Brian Chesky's leadership has been long-term thinking; he has reiterated that one should build a company that can survive for 100 years, a belief that guides him on questions of culture, innovation, and sustainability. This perspective allows Chesky to make decisions that might seem suboptimal in the short term but create sustainable competitive advantages.
The century-scale thinking manifests in Chesky's approach to community building, where he prioritises relationship quality over transaction volume. This patience has enabled Airbnb to build trust gradually rather than pursuing aggressive growth that might undermine long-term brand value.
Values-Driven Decision Making
Chesky continues to see himself in the role of creating a product that's both likable and sustainable. This value-driven Airbnb leadership approach epitomizes Chesky's focus as a community and social leader. The integration of social responsibility into business strategy reflects a maturity often missing from technology leadership.
Chesky's leadership approach offers several practical lessons for executives seeking to build more effective, sustainable organisations. These principles can be adapted across industries and organisational sizes, though implementation requires careful consideration of context and culture.
Implementing Design Thinking in Leadership
Leaders can adopt Chesky's design-centric approach by prioritising user experience in all decisions, not merely product development. This means considering the emotional journey of employees, customers, and stakeholders when making organisational changes. The key is maintaining empathy as a decision-making filter rather than treating it as a separate consideration.
Balancing Detail-Orientation with Delegation
The founder mode philosophy doesn't require micromanagement but does demand intimate knowledge of key processes and metrics. Leaders can implement this by identifying the critical 20% of activities that drive 80% of outcomes and maintaining hands-on involvement in those areas whilst delegating more routine functions.
Building Authentic Community
Chesky's community-building success stems from genuine commitment to shared values rather than marketing tactics. Leaders can foster similar loyalty by identifying authentic ways their organisations can contribute to stakeholder well-being beyond transactional relationships.
What makes Brian Chesky's leadership style unique compared to other tech CEOs?
Chesky's background in industrial design sets him apart from traditional tech leaders. His approach combines artistic sensibility with business acumen, prioritising empathy and user experience in ways that most analytically-trained executives struggle to achieve naturally.
How does founder mode differ from traditional management approaches?
Founder mode emphasises deep product knowledge and hands-on involvement in key decisions rather than broad delegation. As Chesky explains, it means leaders must understand their products better than anyone else in the company, whether that's ice cream, airplanes, or hospitality experiences.
Can Chesky's empathetic leadership style work in other industries?
The principles of empathetic leadership—understanding stakeholder needs, transparent communication, and values-driven decision-making—translate across industries. However, implementation must be adapted to specific organisational cultures and market dynamics.
How does Chesky balance growth ambitions with sustainable practices?
Chesky's century-scale thinking provides a framework for making decisions that might sacrifice short-term gains for long-term sustainability. This approach requires patience and conviction but often creates more durable competitive advantages.
What can traditional companies learn from Airbnb's design-led culture?
Traditional companies can adopt design thinking principles by prioritising customer experience, encouraging creative problem-solving, and maintaining close connections between leadership and actual product or service delivery. The key is fostering curiosity and empathy throughout the organisation.
How does Chesky handle criticism of his favoritism approach?
Chesky maintains that favorites must be chosen based on fair criteria and that transparent meritocracy is preferable to false equality. However, this approach requires careful implementation to avoid creating divisive team dynamics.
What role does humility play in Chesky's leadership success?
Humility has enabled Chesky to gain insights he wouldn't otherwise have obtained, particularly when dealing with regulatory challenges and community concerns. This openness to learning has been crucial for navigating unprecedented situations like the pandemic crisis.
Brian Chesky's leadership style represents a compelling synthesis of artistic vision, empathetic management, and strategic pragmatism. His approach challenges conventional wisdom about delegation and hierarchy whilst demonstrating that sustainable success often emerges from deeper stakeholder relationships rather than purely transactional interactions. As businesses face increasing complexity and stakeholder scrutiny, Chesky's example suggests that leaders who can combine analytical rigor with genuine empathy may be best positioned to build enduring organisations.
The true test of any leadership philosophy lies not in its theoretical elegance but in its practical effectiveness during crisis. Chesky's navigation of the pandemic, regulatory challenges, and competitive pressures whilst maintaining employee loyalty and customer trust suggests that his design-thinking approach to leadership offers more than mere inspiration—it provides a roadmap for building resilient, purpose-driven organisations capable of thriving in an uncertain world.
Like the finest British explorers who combined meticulous preparation with adaptability to unknown terrain, Chesky has charted new territory in management theory whilst maintaining the practical wisdom necessary for sustainable success. His journey from air mattress entrepreneur to transformational leader offers hope that business can indeed be a force for human connection rather than mere economic extraction—a lesson particularly relevant as we navigate an era demanding both innovation and social responsibility.