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Uber’s CEO Conundrum

Uber is getting closer to naming a CEO after a process that has been full of leaks, fiery internal disagreement and at least one top candidate taking to Twitter to say she doesn’t want the job. Throughout it, I’ve often wondered how it is that Uber—already one of the most valuable private companies in history—is struggling to find talent for the job.

Of course, there is all the drama, specifically, the notion that the ride-hailing giant is so damaged that talented leaders are loath to risk their reputations on the top job, even one with a lot of financial upside.   

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I don’t envy the Uber board. Even without the open legal warfare among directors, they are stuck in a hard place. The stunning immaturity of recent years warrants some adult supervision. But there will be a cost to that. I think the best outcome for Uber would be that the culture grows up but that the business gets to stay a teenager a bit longer.

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Uber has to figure out what kind of company it is.