Lessons from Dara Khosrowshahi

Dara Khosrowshahi, the CEO of Uber, is known for his transformative leadership and insightful perspectives on business and life. Since taking the helm of the ride-sharing giant in 2017, he has navigated the company through significant cultural changes and towards profitability.

On Leadership and Management

On the Core Role of a Leader: "You are telling us what to do. You're not telling us where to go. If you tell us where to go, we'll do it because we believe in you.” This was feedback Khosrowshahi received early in his career at Expedia, which he says "really rung a bell for me." He learned that his job wasn't just to give orders, but to "plant a flag" and provide a vision. [1]
On Leading Through Tough Times: "It's the job of the leader to some extent to go against the grain... the good times are when you've got to be the asshole." [2] He clarifies that during good times, leaders should be tougher on their teams to avoid complacency, and during tough times, they should be supportive. [3]
On Decision-Making in Crisis: "During tough times, I'm much more hardcore... you've got to be top down and you've got to solve for speed and you've got to solve for decisiveness." [2]
On Authenticity: After trying to "manage by walking the halls" and finding it awkward and ineffective, Khosrowshahi concluded, "whatever you do whatever advice you choose to take whatever fits in with you. you've got to be authentic." [4]
On Empowering Employees: "Put the right people in the right places, and then you trust them to do the right stuff." [5][6]
On Employee Empowerment and Choices: "You have to empower your employees to make their own choices and trust that they will make the right choices." [6]
On Listening: When he first became CEO of Uber, one of his priorities was to meet with employees, including women engineers. An employee noted, "He didn't come in guns blazing. He came in listening." [7][8]
On the CEO's Blind Spot: "The singular rule of CEO life, is that the higher up you move in a company, the less you really know what's going on." [4]
On Long-Term Vision: Khosrowshahi's management approach is "focused on long-term growth and sustainability. He believes in making strategic investments that will drive future success, rather than pursuing short-term gains." [9]
On Leading with Empathy: "Understanding the needs of employees, customers, and stakeholders fosters trust and loyalty, even in difficult times." [10]

On Company Culture

On Cultural Transformation: "We do the right thing. Period." This simple philosophy was central to transforming Uber's culture from one of "always be hustlin'" to one of accountability and collaboration. [11]
On Evolving Company Values: Khosrowshahi believes that company values are not set in stone. "I think a lot of companies are people view as values are forever they never change i personally think that's BS like companies should be constantly adapting." [2]
On Avoiding Weaponized Values: He noted that a value like "be toe-stepping" at Uber was meant to encourage challenging ideas but was often "weaponized into it's okay to be an asshole." This highlighted the need for a cultural reset. [2]
On Crowdsourcing Culture: To create new cultural norms at Uber, Khosrowshahi and his team "crowdsourced from Uber employees what they thought the best norms cultural values should be." [1][2]
On Diversity and Inclusion: "We celebrate differences. We want to be a different company but we also celebrate differences and background and where you come from and religion and sexuality, et cetera." [4]
On the Importance of a Safe Workplace for Women: When asked how important it is for Uber to be a place where women can feel safe, he replied, "It's 'game over' if we don't." [12]
On Repairing a Toxic Culture: Khosrowshahi understood that "repairing a toxic workplace culture was critical to rebuilding trust and morale." [12]
On Integrity: In establishing new cultural norms, employees "wanted to make clear that we will put integrity at the core of all our decisions." [1]
On a Healthy Organizational Culture: "A healthy organizational culture is the cornerstone of sustainable success. Leaders must foster environments where ethics and collaboration are prioritized." [10]
On Continuous Cultural Work: "I think the cultural transformation, it is hard. It continues. It takes a long time... I'm not comfortable at this point." [4]

On Strategy and Innovation

On Desperation and Innovation: "Desperation sometimes drives innovation." [5][6]
On Speed and Failure: "Failure can teach you something, and as long as you're moving very, very quickly, you're going to start piling up the wins. Speed gives you the luxury to be able to fail." [5]
On Combating Bureaucracy: "As companies get bigger, they tend to slow down. It's a universal law. Our response has been to keep breaking up the company... They don't have to come to me to ask for permission to do something. They just do it." [3]
On Customer-Centricity: Khosrowshahi's leadership style is "deeply rooted in a customer-centric approach. He believes that understanding and meeting customer needs is essential for business success." [9]
On Product and Technology: "If you get the product and technology right, then the rest usually falls into place." [5]
On the Future of Transportation: "We want to create the network around those vehicles so that regular people can take these taxis in the air for longer distances when they want to avoid traffic at affordable prices." [12]
On Autonomous Vehicles: While acknowledging the challenges and the need for safety, he has affirmed that Uber will resume its autonomous vehicle program, stating, "we want to be safe when we get back on the road." [12]
On Competition: When asked for advice for entrepreneurs in the mobility space, he joked, "Don't build anything like Uber because we'll kick your ass." [13][14] He also identified Rapido as a tougher competitor in India than Ola. [13][15]
On Focus: "If some of our competitors are distracted by... love shiny new efforts. and you know IPOs. that's great because I am undistracted. and completely focused on the mobility business here." [16]
On Supply-Led Growth: Khosrowshahi has learned that Uber is a "very supply-led as a company," a realization that has shaped their strategy. [17]

On Life and Career

On His Immigrant Experience: "My family had to flee Iran... the revolution, and we were very, very lucky to come to America and have opportunities presented to us. And that's... one of the things that makes America great." [5][6]
On Gratitude for His Parents' Sacrifices: "When you see the sacrifices that your parents make for you, you want to do well for them." [5]
On the American Dream: "What some Americans don't appreciate is how strong the brand of the American Dream is around the world. I'm an example of how powerful that product is." [5]
On Curiosity: "I have gotten unbelievably lucky in my career, but I've gotten lucky because I'm very, very open to anything... Be curious about meeting new people, be curious about interests that are outside of your immediate field of education. That curiosity will open you up to the world and open you up to opportunity." [18]
On Overplanning: "My advice for young people is don't overplan. You never know what opportunities are going to come up... Being open to possibilities, being open to opportunities, and then when you get that opportunity, going all in." [19]
On Change: "Any time there's significant change, there's going to be some people who embrace the change and others who are against the change."
On Resilience: His early life experience of fleeing the Iranian Revolution "taught young Dara the importance of adaptability and perseverance—qualities that would later define his career." [10]
On Facing Messy Situations: On taking the CEO job at Uber, he said, "It looked messy. And it was messy." [7]
On Travel's Resilience: "We found that travel, especially online travel, has been quite resistant to economic cycles." [6]
On His Personal Life: "My wife and I got married on 12/12/12 in Las Vegas, and she was wearing a Slayer T-shirt. That tells you what kind of woman I'm lucky enough to be with." [6]

Additional Learnings and Insights

Embrace Change: "Life and business are filled with uncertainties. Adaptability and resilience are essential for navigating challenges and seizing opportunities." [10]
Prioritize Culture: "A healthy organizational culture is the cornerstone of sustainable success." [10]
Think Long-Term: "Balancing short-term pressures with long-term goals is crucial for driving innovation and creating lasting value." [10]
Lead with Empathy: "Understanding the needs of employees, customers, and stakeholders fosters trust and loyalty, even in difficult times." [10]
Regain Trust Through Transparency: Khosrowshahi recognized the importance of repairing Uber's reputation by shifting towards ethical practices and accountability.
Data-Driven Decision Making: A key aspect of his leadership is a "focus on data-driven decision making." [9]
Cultivate a Culture of Innovation: He "encourages a culture of experimentation and continuous improvement." [9]
Engage with Stakeholders: A crucial part of his strategy involves engaging with regulators and governments cooperatively. [9]
The Power of Going All In: "If you're going to be in something, go all in, do what's required of you and then 50% more." [19]
On the Importance of a Stable Policy Framework: "In order for businesses like ours to continue to invest etc... we're we need to understand any investment requires us to have some kind of forecast of what's going to happen the next 2 to 5 years. so I think for us the most important part is stability." [16]

Learn more:

Lessons from Dara Khosrowshahi

On Leadership and Management

On Company Culture

On Strategy and Innovation

On Life and Career

Additional Learnings and Insights

Written by Antoine Buteau

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