Remember Undercover Boss, that TV show where executives would go undercover at their companies to see what working life was like for their underlings? Uber’s CEO Dara Khosrowshahi did something similar last year, working as a driver and encountering what he called a “nightmare” scenario.


@fortune Uber CEO reveals his “nightmare” moonlighting as an Uber driver. #uber #uberdriver #ubereats #ubers #lyft #taxi #taxidriver #darakhosrowshahi #ceo #driving #sanfrancisco #sanfran #boss #employee #employer #gps ♬ Sunny Drive - Official Sound Studio


Khosrowshahi’s worst experience wasn’t an unruly passenger or an Uber Eats customer who failed to tip — it was navigating an apartment complex. He told the Wall Street Journal, “I was trying to deliver food, and I couldn’t find where to drop it off. Trying to figure out the maze of apartment complexes was a challenge.”


He also spoke about an order that required him to deliver food to a touch football game: “I was like, ‘Where’s the building I’m supposed to be delivering to?’ It was a field. There was a bunch of dudes.”



This wasn’t Khosrowshahi’s first time working as a driver — in 2021, he tweeted about a San Francisco Giants fan “trying to kill” him in traffic. Through all of this, Khosrowshahi has supposedly learned that the company needs to work harder to make its drivers passionate about what they do. He explained to the WSJ, “Anyone who comes to Uber, they’ve used Uber, they’re passionate about the product, but as an eater or rider. I want that same passion and familiarity as a driver, as a courier, as a merchant, because ultimately, we are a marketplace and we’re helping over five million people a year earn part-time or full-time. That’s an important responsibility, and we’ve got to take it seriously.”



One simple way to do so would be to compensate people fairly, but Uber has thus far seemed disinclined to take this route. Last year, the company successfully sued to block raises for Uber drivers in New York City (later implementing raises of about 8.8 percent following strikes), and has found itself embroiled in a number of legal disputes over the employment status of drivers, with Uber and similar companies fighting to continue to treat drivers as independent contractors rather than employees who are generally entitled to better wages and benefits like sick leave. Many drivers have also criticized the company for unfairly suspending drivers’ accounts, leaving them unable to work.


Needless to say, working a couple of shifts hasn’t led to Khosrowshahi genuinely understanding the needs of Uber drivers and couriers, particularly when they conflict with his bottom line. Maybe he should try earning their paycheck for a few months instead.