Uber CEO Dara Khosrowshahi’s Undercover Boss Moment Led to a ‘Why We Suck’ All-Hands

Dara Khosrowshahi said the company's leadership team didn't understand the shortcomings of Uber's driver products because very few of them ever drove for the apps.

Uber CEO Dara Khosrowshahi
Uber CEO Dara Khosrowshahi speaks onstage during GE The Lean Mindset: The Pursuit Of Progress Event at Chelsea Industrial on September 06, 2023 in New York City. Ilya S. Savenok/Getty Images for GE

One weekend in June of 2021, Uber (UBER) CEO Dara Khosrowshahi hopped on an electric bike near his home in San Francisco and began delivering food for Uber Eats. His Undercover Boss-esque side hustle, initially inspired by Covid boredom, led to the executive discovering many flaws in Uber’s driver apps and eventually calling a company-wide meeting titled “Why We Suck” to share his findings, he revealed at an event this week.

“I was going frickin’ crazy at home during Covid. And I wanted to get the hell out of the house, and I wanted to find some way to be constructive out of the house, so I got an e-bike and I started delivering food for Uber,” Khosrowshahi said at a leadership conference hosted by GE in New York City on Wednesday (Sept. 6).

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On his first day, Khosrowshashi completed 10 trips and earned $106.71 with tips, he tweeted. But he also found the Uber Eats app difficult to use. He struggled with Uber’s sign-up process, which was different for workers wanting to drive people or deliver food. And during deliveries, the app sometimes booked a new order before the previous one was complete, confusing him with two delivery addresses as a result.

“Once I saw what I believe was a lack of quality with the product as it related to delivering, then I bought a Tesla and I started driving as well,” Khosrowshashi said.

In September of 2022, Khosrowshahi signed up as an Uber driver under the alias “Dave K” and began ferrying passengers in San Francisco in his gray Tesla Model Y.

After experiencing the worker side of Uber’s two core businesses firsthand, Khosrowshahi called the aforementioned company-wide meeting to discuss how to improve Uber’s driver products. He said many Uber employees were customers of Uber and Uber Eats, but very few had experience working with either app, so they were less aware of their shortcomings.

“It wasn’t a pleasant all-hands with the company, but it set a tone and we set that expectation,” the CEO said at the conference. “We started celebrating employees going out there delivering, employees driving. It is a point of pride for employees now, when they drive they get a little badge on their corporate profile.”

Khosrowshahi has encouraged several of his lieutenants to go out and drive, too, because “the higher up you go in a company, the less you actually know what’s happening on the ground.”

Uber CEO Dara Khosrowshahi’s Undercover Boss Moment Led to a ‘Why We Suck’ All-Hands