The Deep Dive Leadership Strategy: Brian Chesky's Way

In the corner office of Airbnb, you won’t always find Brian Chesky in a suit behind a polished desk. Sometimes, you’ll find him quietly sitting with a customer service rep, taking notes. Other times, he might be knee-deep in the back-end infrastructure of the platform, questioning how processes work and why. Not to criticize or micromanage – but to understand. To learn. To rethink.

Brian Chesky, the co-founder and CEO of Airbnb, believes in something most CEOs often ignore after their company reaches scale: the deep dive. Every year or two, Chesky plunges into a full audit of a single department, asking everyone to show him the good, the bad, and the inefficient. His goal? To uncover blind spots and push the team to rethink how things are done.

"The only other thing I do is I kind of do deep dives into every function of the company every year or two," Chesky explains. "Beyond checking work, I might do a really deep dive into customer service. And it might be a two to four week audit where I say, hey, no one's gonna get fired. Just show me all the good and bad of the department."

Brian Chesky, Co-founder and CEO of Airbnb Photo: Wired

In this article, we’ll explore why regular, fearless audits can catalyze innovation, examine real‑world examples of companies that swear by the method, and lay out a step‑by‑step guide for implementing your own deep dive strategy.

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Why Every Company Needs a Periodic Deep Dive

Time and again, organizations grow comfortable with “the way things are done.” Managers become gatekeepers of process. Departments evolve in silos. Inefficiencies—like leaky customer support scripts, outdated approval chains, or neglected digital tools—go unnoticed until they become costly bottlenecks.

Most CEOs stop learning once their company hits product-market fit. They start managing from a distance, relying on dashboards, slide decks, and secondhand reports. But companies are living organisms. As they grow, they accumulate complexity, inefficiency, and cultural drift. What worked two years ago might be holding them back today.

A scheduled, company‑wide audit every 12–24 months forces a reset. It’s not about assigning blame; it’s about uncovering latent problems and rethinking systems from the ground up. Chesky notes:

“Every couple years, you need to do a really deep dive on a group because it just needs to be rethought and you can’t defer to managers alone.”

This approach benefits organizations of all sizes:

• Startups get the chance to course‑correct before operating rhythms ossify.

• Mid‑sized firms can reignite entrepreneurial energy.

• Large corporations can capture the agility of smaller teams.

The Starbucks Story: How Howard Schultz Returned to Rescue Culture

Take the story of Howard Schultz, who returned as Starbucks CEO in 2008 during a time of falling profits and declining customer loyalty. Instead of launching a marketing campaign or restructuring teams from afar, Schultz went straight to the stores.

Schultz spent significant time visiting stores, talking to baristas, and understanding their frustrations. Photo: Getty Images

He shut down 7,100 stores for several hours to retrain baristas on how to make the perfect espresso. Yes, he literally stopped revenue to focus on craft. But more importantly, he talked to employees. He listened. He discovered that automation had stripped away the Starbucks magic. So, he reversed it.

This was Schultz’s version of the deep dive. He didn't come back with spreadsheets. He came back with soul.

"Often, organizations need bold, grand gestures to galvanize people towards a new mission or refocus their attention." - Howard Schultz

Creating a Culture of Truth: Safety First

Deep dives work only if teams feel safe to speak up. As Google’s landmark Project Aristotle found, psychological safety ranks highest among factors that predict team success. When employees fear retribution, they’ll cover up mistakes rather than call them out—precisely the opposite of what a deep dive needs.

In most companies, when the CEO comes knocking, people cover their mistakes. They show sanitized versions of reality. But that prevents growth.

Think of Ed Catmull, co-founder of Pixar, who said:

"You are not your idea, and if you identify too closely with your ideas, you will take offense when they are challenged."

At Pixar, they built a culture of radical candor. Film directors regularly subjected their scripts to brutal feedback sessions known as "Braintrust meetings," where anyone could critique anything. Why? Because that’s how masterpieces are made.

Chesky’s approach is similar. He doesn’t audit to criticize. He audits to unlock. To build similar trust in your organization:

1. Set clear ground rules

   • Explicitly state that the audit is a fact‑finding mission, not a witch‑hunt.

   • Ensure confidentiality for candid feedback sessions.
     

2. Lead by example

   • Share your own missteps. When Howard Schultz returned to Starbucks in 2008, he famously admitted, “We lost our soul,” demonstrating vulnerability and resetting cultural norms.
     

3. Follow up transparently

   • Publish a summary of findings and planned actions. Transparency shows that feedback truly matters—and that leaders aren’t simply checking a box.

Case Study: The Pandemic Deep Dive That Saved Airbnb

The most dramatic example of Chesky's deep-dive leadership philosophy came during the COVID-19 pandemic, when Airbnb faced an existential crisis that would have destroyed most companies. Within eight weeks, Airbnb's business dropped 80 percent, forcing Chesky into the deepest organizational dive of his career.

Rather than retreating to the executive suite to strategize, Chesky immersed himself in every aspect of the crisis response. He personally reviewed every single one of the 1,900 layoffs, ensuring that decisions weren't made by algorithm or middle management, but by someone who understood both the human cost and strategic necessity of each cut.

But here's where Chesky's approach differed from typical crisis management. Instead of just making cuts, he dove deep into what the post-pandemic company should look like. The crisis revealed that Airbnb had become "the equivalent of a ten-division company" that needed to be transformed into "a single-division functional organization". This wasn't just downsizing—it was fundamental redesign based on intimate operational understanding.

The deep dive revealed crucial insights that only came from ground-level engagement. Chesky discovered that searches—a leading indicator for bookings—were showing recovery signs by mid-May 2020, but it wasn't the business they'd known before. Traditional business travel and international tourism were gone, but people wanted to gather with family and friends in nearby locations.

This led to the "Go Near" campaign and a complete pivot of the company's focus. More remarkably, Chesky took $250 million from Airbnb's balance sheet and gave it to hosts, despite the company struggling to raise equity at the time. This decision came from his deep understanding that "our hosts are our lifeblood. If they aren't solvent, we are not solvent".

The results speak for themselves. A company that bankers said would never go public that year not only survived but staged one of the most successful IPOs in history just months later. The deep dive hadn't just identified problems—it had revealed the company's true adaptive strengths.

The S-1 Deep Dive: Rewriting Airbnb's Story

Another powerful example of Chesky's deep-dive approach came during Airbnb's IPO preparation. When the company decided to go public in July 2020, Chesky discovered that their original S-1 filing "described a company that no longer existed" due to all the changes made during the pandemic response.

Rather than delegating this critical document to lawyers and bankers, Chesky personally wrote around 14,000 words of the filing. He approached the S-1 not as a regulatory requirement, but as a deep dive into the company's fundamental identity and purpose.

"Writing the founders' letter was, surprisingly, more difficult than the layoff letter," Chesky reflected. "The layoff letter was difficult emotionally, but I just had to tell people what was happening step by step." The S-1 required him to distill Airbnb's essence into three core principles: why they exist, their creative spirit, and their 21st-century approach to stakeholder capitalism.

This deep dive into the company's purpose led to concrete innovations, including the creation of a special stakeholder committee on Airbnb's board and the Airbnb Host Endowment—funded with 9.2 million shares plus $100 million of Chesky's personal equity. These weren't just PR moves; they were structural changes that emerged from his deep examination of what Airbnb should become.

The result was an S-1 letter unlike anything investors had seen before, one that positioned Airbnb not just as a booking platform, but as a community-driven company built for the long term. The market responded enthusiastically, validating Chesky's belief that deep understanding translates to strategic advantage.

The "Love" Letter: A Deep Dive in Crisis Communication

Perhaps the most revealing example of Chesky's deep-dive philosophy came in how he approached the most difficult communication of his career—the letter announcing Airbnb's pandemic layoffs.

Chesky's approach to writing the layoff letter demonstrates his deep-dive methodology in action. He didn't treat communication "like waiters treat food: other people cook it, and the waiter has to serve." Instead, he dove deep into the psychology of both audiences: employees keeping their jobs and those being laid off.

His analysis revealed that traditional corporate communications fail because they prioritize legal safety over human connection. "I would rather say a couple of wrong things and embarrass myself, but at least people know I'm speaking from the heart, than execute it coldly and perfectly," he explained.

The deep dive led to radical departures from standard corporate practice. Chesky ended the letter with a four-letter word he admits "you are not supposed to use in business"—love. He personally reached out to peer CEOs asking them to consider laid-off Airbnb employees. The company converted part of its recruiting team into an outplacement firm and created an alumni directory that helped over 1,000 former employees find new jobs.

This wasn't just compassion—it was strategic thinking based on deep understanding of stakeholder psychology. The approach generated enormous goodwill that proved crucial to Airbnb's recovery, with the letter becoming a case study in crisis communication taught at business schools worldwide.

Lessons from Other Companies

While Chesky’s deep dives are legendary in tech circles, he’s far from the only leader to champion regular audits:

Patagonia

Patagonia, the outdoor clothing company, exemplifies this approach in its environmental and social responsibility efforts. When founder Yvon Chouinard decided to investigate his company's supply chain practices, he didn't just review reports—he and his team visited factories, talked to workers, and examined environmental impacts firsthand. What they discovered led to fundamental changes in how Patagonia sources materials and manufactures products.

Chouinard's philosophy has always been driven by a deep personal commitment to environmentalism. Photo-Campbell Brewer

The key was Chouinard's willingness to confront uncomfortable truths about his company's practices and his commitment to making changes based on what he learned, even when those changes were costly or difficult.

Toyota

"Genchi Genbutsu" (現地現物) is a core tenet of the Toyota Production System and Lean manufacturing. It literally translates to "go and see for yourself." It means that in order to truly understand a situation, solve a problem, or make an informed decision, one must go to the actual place (genchi) where the work is happening and observe the actual things (genbutsu) and facts firsthand, rather than relying on reports, data summaries, or assumptions from afar.

Toyota's legendary production system wasn't developed in conference rooms; it emerged from detailed observation of factory floors, deep analysis of workflow patterns, and continuous iteration based on real-world feedback.

The Competitive Advantage of Organizational Intelligence

In an era where competitive advantages are increasingly ephemeral, deep organizational knowledge represents a sustainable differentiator. Competitors can copy products, poach talent, and replicate strategies, but they can't easily replicate the institutional intelligence that comes from systematic deep diving.

This intelligence manifests in multiple ways: faster problem identification, more accurate resource allocation, better prediction of operational challenges, and stronger connection between strategic decisions and operational reality. It's the difference between managing a company and truly understanding it.

Amazon's Jeff Bezos exemplified this approach throughout his tenure as CEO. Despite Amazon's massive scale, Bezos maintained involvement in detailed operational decisions, from warehouse layout optimization to customer service protocols. His famous annual letter to shareholders often included specific operational insights that could only come from deep engagement with the company's day-to-day operations.

Tactical Deep Dive Blueprint

For those wondering how to implement this, here’s a simple framework:

1. Choose One Department: Pick one area where growth has stalled or complaints are rising.
   

2. Announce the Deep Dive with Safety: Clearly state that this is not a witch hunt. People won’t be fired for honesty.
   

3. Shadow, Don’t Intervene: Spend 2-4 weeks observing, asking questions, collecting stories. Not directing.
   

4. Find the Good, Bad, and Weird: Document what’s working, what’s broken, and what doesn’t make sense anymore.
   

5. Workshop New Ideas: With the team, brainstorm how to reimagine the system. Don’t just optimize. Reinvent.
   

6. Follow Through: Support the implementation of changes. Don’t vanish after the audit.

Final Thoughts: The Courage to Care

Brian Chesky's deep dive philosophy represents more than just a management technique—it's a fundamental approach to leadership that prioritizes understanding over assumption, engagement over delegation, and truth over comfort. In a business world often characterized by distance between leadership and operations, it offers a powerful alternative.

The approach requires courage—the courage to confront uncomfortable truths about your organization, to invest significant time in operational details, and to remain connected to the ground-level reality of your business even as it grows and evolves.

But for leaders willing to make this investment, the rewards are substantial: organizations that are more efficient, more responsive to problems, and more capable of adapting to change. Most importantly, they develop the kind of deep organizational intelligence that can't be easily replicated by competitors.

So the next time your business feels stuck, don’t just launch a new strategy. Do something braver: Dive in. Look around. Listen deeply. And lead from the inside out.

Because sometimes, the best way to grow is to rethink everything you already built.

Ready to harness the power of focus and transform your business? Subscribe to our newsletter for weekly insights, tips, and stories to help you stay focused and achieve your goals!

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Source: Brian Chesky - Founder Mode & The Art of Hiring