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, 2023

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

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Rita McGrath

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