Airbnb CEO Reflects on Emotional Messaging During Layoffs

Ethan Bennett
By Ethan Bennett 93 Views Add a Comment

In a recent podcast, Airbnb CEO Brian Chesky opened up about the emotionally charged messaging he used during the company’s 2020 layoffs, which saw nearly 2,000 employees let go. Chesky’s heartfelt language, while well-intentioned, has since been scrutinized and reflected upon, revealing insights into the complex relationship between corporate leadership and employee communication.

In May, Chesky appeared on Adam Grant’s podcast ReThinking, where he discussed the aftermath of the significant layoffs Airbnb executed in response to the global travel restrictions brought on by the pandemic. The company, which prides itself on a culture of belonging and community, had to let go of 1,900 employees, almost a quarter of its workforce. Chesky’s message to those affected was laden with personal sentiment, stating, “I have a deep feeling of love for all of you,” a phrase that has since garnered mixed reactions.

The reason I used the word love is ’cause that’s what I felt at the time.

Brian Chesky

Reflecting on his choice of words, Chesky admitted that he might have fumbled the messaging. “The reason I used the word love is ’cause that’s what I felt at the time,” he explained, acknowledging that the letter was written under significant time pressure and emotional strain. Despite the intention to convey empathy, the use of familial language like “love” and “family” during such a turbulent time came across as misplaced to many.

The contrast between Airbnb’s intended message of compassion and the reality of a business-driven decision became apparent. Chesky noted that, while Airbnb’s culture emphasized collaboration and a sense of belonging, the layoffs exposed the fundamental nature of the company as a business entity, not a family. “How does a company whose mission is centered around belonging have to tell thousands of people they can’t be at the company anymore?” he pondered.

In his podcast appearance, Chesky candidly discussed the dissonance between the company’s culture and the harsh realities of business decisions. He admitted that referring to the company as a family might have been a mistake. “It is true that a company is not a family. In fact, we had to make that pivot,” he said. “We used to refer to ourselves as a family, and then we did have to fire people or they’d have to leave the company and yeah, you don’t fire members of your family.”

This shift in perspective aligns with a broader criticism of the “company as family” narrative, which has been increasingly viewed as a red flag for potentially toxic workplace environments. Leadership expert Joshua A. Luna, in a Harvard Business Review blog post, highlights the risks of this metaphor, pointing out that it can obscure the inherent hierarchies and professional boundaries necessary in a workplace.

Despite backing away from the family-based culture, Chesky maintained that fostering trust and meaningful connections within the team remains vital. He wanted to ensure that those who left felt supported, offering vested equity and leveraging Airbnb’s network to help them transition. “There can be a bond that can be deeper than a typical work contract,” he noted, emphasizing the importance of humane and respectful communication, even in difficult situations.

It is true that a company is not a family. In fact, we had to make that pivot.

Brian Chesky

Chesky’s reflections underscore the challenges leaders face in balancing empathy and professionalism, particularly during crises. His intention was to differentiate Airbnb’s approach from the often impersonal and sterile nature of corporate layoff notices, which he described as “inhumane” and “like an AI prompt.” By contrast, Chesky aimed to convey a more compassionate and human touch, albeit with mixed success.

In retrospect, Chesky’s experience serves as a poignant example for leaders navigating the delicate terrain of organizational communication during difficult times. The lessons learned from Airbnb’s 2020 layoffs highlight the importance of sincerity, clarity, and the need to balance emotional intelligence with practical business considerations.

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Ethan Bennett is a financial expert and lead author at With a passion for finance and technology, Ethan provides readers with the latest insights on banking and investment. He holds a Master’s Degree in Finance from Harvard University. With over fifteen years of experience in top financial institutions, Ethan excels in wealth management and digital banking. At, he ensures all content is accurate and valuable, making complex financial topics accessible and engaging for readers.
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