When you're the CEO of the world's most valuable - and probably most turbulent - private company, something great or downright terrible could happen at any moment.
For example, when the news of Uber's attempt to cover up a data breach of 57 million user accounts in 2016 came out, new CEO Dara Khosrowshahi found himself once again repeating the phrase that seems to be developing into a bit of a mantra: "We will learn from our mistakes."
What Khosrowshahi does have going for him is the fact that he and former CEO Travis Kalanick are strident opposites. The latter founded the company and rode it like a bull for seven years, the former is in his fourth month in office and hopes to repave the broken road ahead.
Below is an analysis of exactly how opposite the Uber leaders are--which is something the global ride-hailing giant is betting on to get it out of the media cage it's gotten itself into.
- Kalanick breaks rules, Khosrowshahi makes rules. Khosrowshahi wrote on LinkedIn that Uber is moving "from an era of growth at all costs to one of responsible growth."
- Kalanick says, "look", Khosrowshahi says "listen". If you watch both men speak in interviews for any length of time, they begin their responses with similar idiosyncrasies, but their word choice illustrates a subtle difference: Kalanick's "look" is like finger-pointing and Khosrowshahi "listen" is more invitational.
- Kalanick has a proclivity for public hubris, Khosrowshahi tends toward humor. Kalanick is known for his temper, while Khosrowshahi isn't afraid to crack a joke. When one Bloomberg reporter tweeted: "General belief is that [Khosrowshahi] has six months of slack until he starts getting tagged with Uber's problems," Khosrowshahi replied on Twitter, "Phew, I can coast a bit until March. Then I gotta get going ..."
- Kalanick is a salesman, Khosrowshahi is a manager. One entrepreneur who has worked with Kalanick described him as "ego personified." Khosrowshahi wrote on LinkedIn, "But I'm different from many of these young CEOs in that I'm not [a] founder... I'm what you'd call 'professional management.'"
- Kalanick is rough around the edges, Khosrowshahi is as straight-edge as it gets. While the former has a dotted past of ignominious incidents, the current CEO is a family man with a clean reputation and a strong business track record.
- Kalanick is an innovator, Khosrowshahi a sculptor. Kalanick came up with the idea for Uber and raised billions - no small task by any means - but lacks the finesse and articulation required to lead an enterprise through messy political and compliance issues.
- Kalanick apologizes for what he's done, Khosrowshahi apologizes for what he's not done. While Kalanick wrote a profound apology for his vitriolic outburst with an Uber driver, Khosrowshahi wrote an apology letter to London regulators saying, "On behalf of everyone at Uber globally, I apologize for the mistakes we've made."
- Kalanick is a disruptor, Khosrowshahi is a stabilizer. Anyone who changes the world is going to step on toes. But Khosrowshahi is correcting Kalanick's example. "For instance, 'toe-stepping' was meant to encourage employees to share their ideas regardless of their seniority or position in the company, but too often it was used as an excuse for being an asshole."
- Kalanick is self-reliant, Khosrowshahi is self-aware. While Kalanick might pull a fast one (like make unauthorized board appointments), Khosrowshahi doesn't take sides, equips his team with positivity, and is honest about knowing what he does and doesn't know.
- Finally, Kalanick has a startup background, Khosrowshahi has an executive background. Kalanick's career before Uber involved creating a couple of peer-to-peer file-sharing startups. Khosrowshahi was an investment banker before he became the CEO of global travel booking brand Expedia and led the company to quadrupled growth.
Uber is no longer a tech startup. It's a global corporation. Managing a global corporation takes a different set of leadership skills than growing a tech startup. Kalanick's "Ready, fire, aim" is out and Khosrowshahi's polished poise and professional repertoire are in. And while it's still too early to tell if Khosrowshahi has what it takes, it seems he might be the type of chief Uber so desperately needs as it heads towards IPO in 2019.