Uber's CEO became an undercover boss in a used Tesla and was surprised by how rude some riders can be

• Uber's CEO moonlighted as a driver last September to better understand why recruitment was an issue.
• Dara Khosrowshahi told The Wall Street Journal he encountered problems that discouraged drivers.

Uber's CEO moonlighted as a driver to find out why the company was having trouble signing up more drivers. He was surprised to find out just how many issues there were — and how unpleasant some riders could be.

Dara Khosrowshahi, the CEO of Uber, told The Wall Street Journal that he secretly signed up as a driver in September last year to better understand the Uber-employee experience amid a slowdown in recruitment.

The company had traditionally focused on the rider experience, but he said it also needed to win the "hearts and minds" of drivers to maintain its lead over rivals such as Lyft.

He bought a secondhand Tesla Model Y to ferry riders around San Francisco and make deliveries using the alias "Dave K."

While there were several operational issues that made using the app difficult, some customers' behavior unpleasantly surprised Khosrowshahi.

The Journal reported that some experiences — such as riders discussing personal problems or confidential corporate information as if they were the only people in the car — made him feel slighted.

When Khosrowshahi made food deliveries using an electric bike, he often encountered a practice called "tip-baiting," where customers entice a courier with a big tip when they place the order, before reducing it after delivery.

Another passenger who recognized the CEO on one of his Uber shifts asked him for advice on his startup.

Khosrowshahi told the Journal he had a five-star rating for the roughly 100 rides and deliveries he'd completed around town.

However, he said he'd go to bed anxious about maintaining his perfect rating the next day.

Khosrowshahi said he would try to keep customers happy by offering them charging cables and making Spotify playlists featuring artists including Taylor Swift and The National.

Five Uber drivers recently interviewed by Insider said they frequently encountered rudeness, no tips, late arrivals, and requests for stops at drive-thrus or convenience stores.

Khosrowshahi's moonlighting was part of a bigger operation called "Project Boomerang" that aimed to get more drivers back on the app.

The findings prompted Uber to create a single sign-up for both rides and deliveries, to allow drivers to see drop-off locations before pick-up, and to give drivers hundreds of millions of dollars in bonuses.

Khosrowshahi told the Journal that some drivers had returned in response to economic uncertainty, which, at the time, did not have an impact on rider demand.