Taking it to the streets — Uber CEO finds out what it’s really like to be an Uber driver

Rita McGrath
6 min readApr 27

CEO’s make a lot more money, have a lot more autonomy and enjoy a lot more control, than the people working for them. The danger is that they can develop incredible blind spots, lose the trust of their people and generally look like the A**holes my buddy Bob Sutton talks about. One antidote? Take some time on the front lines of your business.

Uber — best of startups, worst of startups

Over the years, I have had my quibbles with Uber’s business model. Their use of massive amounts of free money to subsidize both riders and drivers, their bullying localities into depriving licensed cab services from income and their notion that network effects will give them a lasting advantage have all led me to question its business model.

But, hey, here’s a place where Uber’s CEO, Dara Khosrowshahi, gets major brownie points in my eyes. He took a page out of the playbook of the worlds’ most successful retail leaders and decided to put himself on the front lines of the customer experience. He decided to become an Uber driver! Wow, that’s taking a major step forward into understanding what’s going on at the ‘edges’ of his business.

Project Boomerang

Post-pandemic, attracting and retaining drivers has been one of Uber’s biggest challenges. Riders were back, ready and willing, but drivers? Not so much.

As Khosrowshahi told the Wall Street Journal, “I think that the industry as a whole, to some extent, has taken drivers for granted,” He hadn’t driven on Uber before because it wasn’t his biggest priority — drivers had always been in abundant supply. The pandemic-fueled labor shortage forced a companywide introspection, he said, to “re-examine every single assumption that we’ve made.”

Carol Chang, Uber’s head of driver operations, is credited with coming up with the idea of having executives at the company, beginning with the CEO, experience first-hand, what their drivers were going through. In a mind-blowing 227 page presentation, she pointed out that the company was its own worst enemy. As the Journal reports, she outlined how the company’s three competing objectives of keeping costs low, avoiding legal…

Rita McGrath

Columbia Business School Professor. Thinkers50 top 10 & #1 in strategy. Bestselling author of The End of Competitive Advantage & Seeing Around Corners.