When I came across a LinkedIn video of Airbnb CEO Brian Chesky claiming that he avoids one-on-one meetings, my immediate reaction was disbelief. I had just finished reading Nancy Lyons’ article on Mark Zuckerberg’s transformation and the troubling resurgence of toxic bro culture in tech, so the timing couldn’t have been more perfect. I was stunned and, frankly, pissed off, so I quickly shared the video with Greg, voicing my shock. Could this really be true? Or is it yet another example of toxic leadership practices infecting modern workplaces?
Zuckerberg recently declared that corporate culture needs "more masculine energy," and Chesky’s perspective somehow feels eerily aligned. Both reflect a leadership style that devalues empathy and connection in favor of a shallow, outdated notion of "strength." As Nancy Lyons aptly put it: “Leadership in tech must become less about power and control and more about accountability, humanity, and inclusion.”
Here’s the truth: great leadership doesn’t come from shutting people out or dominating conversations. It comes from listening, learning, and creating spaces where all voices can be heard.
This article is a rallying cry to all men in leadership positions: it’s time to stop running from empathy. Practicing empathy doesn’t make you weak; it makes you the kind of leader people want to follow. Empathy creates stronger, more inclusive, innovative, and proactive teams. Avoiding one-on-one meetings? That’s not innovative. It’s an outdated relic of a leadership style that doesn’t value humanity.
Let’s dissect Chesky’s remarks with three quotes from the video, some of the most striking user comments from LinkedIn, and a healthy dose of outrage.
The CEO's stance: "Almost no great CEO in history has ever done them."
Chesky’s claim that one-on-ones are "fundamentally flawed" because employees "own the agenda" is both dismissive and uninformed. He argues that employees bring up topics managers don’t want to discuss. Newsflash: that’s precisely the point! Leadership isn’t about cherry-picking conversations to suit your comfort zone; it’s about tackling the tough stuff.
According to a Gallup study, employees with regular one-on-ones with their managers are 3x more likely to be engaged at work—a big problem in the workplace today as we know from Greg's blog posts from last week and the week before. Avoiding these interactions doesn’t just undermine engagement — it sends a message that employees’ voices don’t matter unless they align with the CEO’s priorities.
The kicker? Chesky doubles down, claiming CEOs historically didn’t do one-on-ones either. Sure, but history also gave us workplace smoking, rampant nepotism, and open-floor office plans. Progress isn’t about clinging to what was; it’s about learning what works and doing better.
"You become like their therapist."
Let’s unpack this gem. Chesky laments that one-on-ones force him to "become like their therapist," as if lending an empathetic ear is beneath the role of a leader. LinkedIn user, Jonathan O., summed up the absurdity perfectly in his reply in the post thread:
"This is truly astonishing and far from the conduct expected of a modern CEO. His one-on-one calls are nothing more than standard conversations between two people, much like the rest of us experience daily. If I were in his shoes, reviewing this piece or observing the body language, I’d be deeply embarrassed."
One-on-ones aren’t therapy sessions! They’re opportunities to build trust, understand challenges, and support your team in meaningful ways. Leaders are meant to listen to their teams. If that means employees share issues or complaints, then sorry not sorry — that’s part of the job. Ensuring a positive employee experience is one of the core responsibilities of a leader.
Dismissing this responsibility as "therapy" is not only insulting but also a glaring sign of a leader who hasn’t created a psychologically safe space. When employees don’t feel safe to voice concerns, it leads to disengagement, resentment, and a lack of trust. Chesky’s comments reveal a fundamental misunderstanding of what leadership entails. Empathy isn’t a weakness — it’s a necessity. If you can’t handle that, maybe leadership isn’t the right lane for you.
"Topics can also arise that would benefit other people at the company to hear."
This argument is almost impressive in its misjudgment. Chesky implies that group meetings are more effective because "topics can also arise that would benefit other people at the company to hear." Sure, because nothing says inclusivity like ensuring only the loudest voices dominate the room.
Amber P., a senior leader on LinkedIn, hit the nail on the head with their reply:
"It’s far too easy in group settings for 1 or 2 voices to dominate the discussion. Too often, female voices go completely unheard as they are overridden, ignored, or because they don’t feel comfortable enough to speak up. If there are never any follow-up 1:1’s, you’re limiting diversity of thought and creating an echo chamber."
Amber’s point is crucial: one-on-ones are the antidote to the echo chamber. By ignoring these opportunities, leaders reinforce a culture where marginalized voices are silenced. This isn’t just a managerial misstep; it’s a microaggression against the principles of diversity, equity, and inclusion (DEI).
While our government actively guts DEI initiatives and silences dissenting voices, leaders like Chesky are setting similar precedents in the workplace. By removing opportunities for one-on-one communication, they perpetuate a culture of exclusion. This behavior isn’t just toxic — it’s dangerous.
The value of one-on-ones
Let’s talk about what Chesky’s missing:
- 71% of employees who have regular one-on-ones report higher job satisfaction (SHRM).
- Managers who hold consistent meetings are 2.3x more likely to identify team members at risk of burnout (Harvard Business Review).
Steven G. Rogelberg, an organizational psychologist, responded beautifully:
"The outcomes associated with effective one-on-ones are amazing. When the worker leads the conversation, it boosts engagement, productivity, and overall happiness."
Avoiding one-on-ones might save you 25 minutes a week, but it costs you invaluable insights and relationships. Great leaders know that time spent listening to their team is an investment, not a chore.
Final thoughts
Chesky’s dismissive stance on one-on-ones isn’t just disappointing — it’s a masterclass in how not to lead. Empathy and humanity are the cornerstones of effective leadership, and refusing to engage in meaningful, one-on-one dialogue shows a fundamental misunderstanding of what it means to connect with your team.
This issue goes beyond Chesky. It reflects a broader trend in leadership, where men like Zuckerberg push for aggressive goals under the guise of "masculine energy," effectively sidelining voices that challenge their worldview. This toxic bro culture cannot become the norm.
As a male leader, I believe it’s my responsibility to stand up against these behaviors. We need to advocate for inclusive, human-centered workplaces. We can have ambitious goals and foster a culture of hard work and performance without making it "masculine." It’s time to lead with empathy, courage, and conviction — because real leadership isn’t about power; it’s about people.
