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In a business world often dominated by delegation and high-level strategy, Airbnb co-founder and CEO Brian Chesky stands apart with a leadership philosophy that challenges modern conventions. Chesky advocates for a hands-on approach that keeps executives deeply connected to their company's products and people—a perspective that might feel counterintuitive in an era of remote leadership and extreme delegation, yet has proven remarkably effective for some of the world's most innovative companies.
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The Chief Editor Mindset
"You have to be in the details. You have to be close with them. You have to, as a CEO, set not only the vision but the rhythm"
Chesky explains this with the conviction of someone who has learned this lesson through experience rather than business school textbooks.
This isn't just philosophical musing—it's a practical approach Chesky employs daily at Airbnb.
"I review all the work now before it ships. I am the chief editor of the company"
This level of involvement might sound excessive to those trained in contemporary management theory, but Chesky sees himself as part of a lineage of visionary leaders who maintained close connections to their company's output.
"This flies in the face of everything we're taught about modern leadership, except when you go through history, many of the best companies in history, from Steve Jobs to Walt Disney to today with Jensen, Elon, or many others, they're people that are in the details."
Beyond Micromanagement: The Detail Distinction
The immediate objection to Chesky's approach is predictable: Isn't this just micromanagement dressed in founder's clothing? Chesky anticipates this criticism and draws an important distinction.
"A lot of people, they hear this, they say, wait, isn't that like micromanaging? There is a difference. You can be in the details of people without telling them what to do, working through problems with them."
This distinction might be best illustrated through a story that circulated within Airbnb's design team a few years ago. During a crucial redesign of the platform's review system, the team had prepared multiple options for displaying host and guest feedback. They were confident in their recommendation but brought all versions to a review meeting with Chesky.
Rather than simply approving or rejecting options, Chesky asked questions that revealed genuine curiosity: "What problem were you trying to solve with this approach?" "How did users respond in testing?" "What were the tradeoffs you considered?" The team didn't leave with direct orders but with deeper insights about the product's goals and user needs.
As one designer later reflected, "Brian wasn't telling us what to do—he was helping us think better about what we were doing. There's a world of difference in how that feels on the receiving end."
The Accountability Paradox
Chesky presents a logical challenge to leaders who claim they simply hire great people and get out of their way:
"And by the way, if your argument is you hire great people and you empower them to do their job, how do you know they're great if they're not in the details? Why are you not in the details but the board is auditing you? If you're not in the details, you have leaders not in the details."
This reveals what might be called the accountability paradox of modern leadership. CEOs are ultimately responsible for a company's performance, yet many operate at such an abstract level that they have limited visibility into the actual work being produced.
Consider the contrast between two hypothetical CEOs facing a product delay:
CEO Adam runs a software company with a traditional delegation approach. When a major feature falls behind schedule, he receives a high-level report with sanitized explanations from his executive team. The true causes—an architectural decision made months ago, growing technical debt, and communication gaps between engineering teams—remain obscured from his view.
CEO Briana takes Chesky's approach at her comparable company. Because she regularly reviews work-in-progress and participates in key product discussions, she spots concerning patterns weeks before they become critical. When the same potential delay emerges, she can ask informed questions that help the team address root causes rather than symptoms.
Presence vs. Absence: The Leadership Equation
At the heart of Chesky's philosophy is a fundamental belief about what leadership should be:
"This is about a mentality of belief that great leadership is presence, not absence. And most CEOs of most companies are not present. They're fairly absent."
This distinction between presence and absence may be Chesky's most profound insight. Leadership presence isn't simply about physical location or calendar time—it's about mental engagement with the substantive work of the organization.
The CEO as Chief Product Officer
Chesky takes his philosophy to its logical conclusion with a bold assertion about the CEO's role:
"I believe the CEO should be the chief product officer of the company. Why? Because the purpose of a company is to make a product. And so why wouldn't the CEO be the expert of the product?"
This perspective might seem radical in companies where CEOs come from finance, sales, or operational backgrounds with limited product experience. Yet Chesky's argument has historical weight. From Henry Ford's obsession with manufacturing details to Steve Jobs' legendary product reviews, many iconic business leaders have maintained intimate connections with their company's offerings.
The story of Reed Hastings at Netflix provides an illuminating example. Though Hastings had a technical background, as Netflix grew he faced the common pressure to "elevate" into a more removed leadership role. Instead, he continued participating in product and algorithm discussions, maintaining enough technical fluency to engage meaningfully with engineering teams even as the company expanded globally.
When Netflix was developing its recommendation system—a core competitive advantage—Hastings didn't simply approve budgets and timelines. He engaged with the technical approach, understood the algorithms being deployed, and could articulate how these systems connected to the company's broader strategy. This wasn't micromanagement but rather informed leadership that ensured technical decisions aligned with Netflix's vision.
Applying the Chesky Principle
What might Chesky's approach look like for leaders who want to implement this philosophy without creating bottlenecks or undermining team autonomy?
Create Visibility Mechanisms
Effective "in the details" leaders create systems that make important work visible without requiring their constant presence. This might include regular product reviews, rotating project deep-dives, or "skip-level" sessions with team members several layers below them.
Ask Better Questions
The goal isn't to direct every decision but to understand how decisions are being made. Leaders can develop questioning techniques that reveal thought processes without imposing solutions.
Develop Domain Expertise
Being "in the details" requires actual knowledge. Leaders should invest time in understanding their company's core technologies, methodologies, and creative processes—not to become practitioners, but to be informed evaluators.
Create Feedback Loops
Chesky doesn't just review work—he participates in a dialogue about it. This means establishing clear channels for teams to respond to leadership input and explain their rationale.
Model the Behavior
If the CEO is engaged with product details, other leaders are more likely to follow suit. This creates a culture where meaningful engagement with the work becomes the norm rather than the exception.
A Return to Fundamentals
What makes Chesky's perspective particularly valuable is that it represents not a new management fad but a return to fundamental principles that have produced extraordinary results throughout business history.
"This is not about being a founder," Chesky clarifies. "It turns out this is the natural way for founders to run it. But this is not a this versus that. This is not about non-founders."
In other words, the principles of engaged leadership transcend founder status or company stage. They apply whether you're running a five-person startup or a global enterprise with thousands of employees. The mechanisms and systems will differ, but the core philosophy—that leadership requires presence and engagement with the details—remains constant.
In an age where leadership is often discussed in terms of vision statements and culture decks, Chesky offers a refreshingly concrete alternative: Get in the details. Know the work. Be present, not absent. It's a philosophy that challenges contemporary wisdom but may ultimately produce more innovative, aligned, and successful organizations.
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