Uber CEO's most nightmarish experience as a driver came when he was delivering food and couldn't figure out the 'maze of apartment complexes'

• Uber's CEO Dara Khosrowshahi told The Wall Street Journal that the worst part of Uber driving was food delivery.
• Khosrowshahi said he got lost driving through a "maze of apartment complexes" during a delivery.

Now that he's tried it out for himself, Dara Khosrowshahi, the CEO of Uber, may have a better understanding of what it's really like to be delivery driver for his company.

When asked the most nightmarish rider experience he had as an Uber driver, Khosrowshahi said that it wasn't the riders that gave him issues — it was delivering food.

"I was trying to deliver food and I couldn't find where to drop it off," Khosrowshahi told The Wall Street Journal. "Trying to figure out the maze of apartment complexes was a challenge."

Navigating large apartment complexes has been a pain point the company, an Uber spokesperson told Insider, adding that the company has tried to address this by providing users with more accurate drop-off pins.

Uber Eats wasn't all bad, though.

"The most fun was delivering food to a touch football game," Khosrowshahi said. "I was like, 'Where's the building I'm supposed to be delivering to?' It was a field. There was a bunch of dudes."

Still, Khosrowshahi seems to be aware that Uber drivers face a series of challenges during their shifts.

Improving the company's working conditions for its drivers starts with corporate Uber employees "using our products" and "getting in the shoes of a driver," he added.

Khosrowshahi moonlighted as an Uber driver last September to understand why the company was seeing a slowdown in recruitment for drivers around that time.

The CEO previously told the Journal that he was surprised by what he encountered on the job.

When he made food deliveries using an electric bike, Khosrowshahi said he often faced a practice called "tip-baiting": customers would lure couriers with big tips only to reduce them after the delivery was made. Tipping, drivers say, is imperative to earning a livable wage.

When driving riders to their destinations, Khosrowshahi said there were times when his passengers would discuss their personal issues, expose confidential corporate information, and even ask him for advice, the Journal reported.

Uber drivers have also complained about riders being loud and obnoxious, slamming doors, leaving crumbs on the seats, and running late.

In terms of wages, certain local governments have taken matters into their own hands. Last month, New York City passed a law that would require delivery drivers to earn at least $18 an hour, and Minneapolis recently advanced a bill that would raise the pay of rideshare drivers.

While Khosrowshahi has encountered the issues of being a driver, the recent experience of a passenger surprised him. He was floored to learn a 2.95-mile Uber ride from downtown New York City to the city's West Side cost $51.69.