In today’s tech-driven culture, the term CEO is often synonymous with Founder.

And both terms possess the power to inspire a cult of personality verging on hero worship.

So when the understated dark horse Uber CEO candidate Dara Khosrowshahi was chosen to succeed Travis Kalanick, it was unexpected news.

But perhaps it was welcome news from another cultural angle:


In a recent LinkedIn post, leadership and culture expert Andrew Mikhail likened this summer’s cultural unraveling at Uber to a blooper reel: sans the humor but with a massive dose of toxicity tossed in for drama.

And, as Mikhail points out, “toxic cultures will eventually bring organizations down.”

And indeed the same day Dara Khosrowshahi’s appointment was announced, The Department of Justice (DOJ) had an announcement of their own: an early-stage investigation into whether Uber violated the Foreign Corrupt Practices Act — a law prohibiting bribery of foreign officials in the pursuit of global business expansion.

This, in addition to a major lawsuit from driverless car company Waymo, a recent settlement with the FTC around user privacy, and another allegation from the DOJ that Uber drivers have access to software enabling them to hide from the police.

Truly, toxicity spreads like wildfire – especially if it starts with the CEO.

So for Khosrowshahi, the urgency to reboot Uber’s culture is palpable…but how to begin such a daunting task?

If you were in his shoes, what would you do first?

To answer this overwhelming question, we sought insight once more from Andrew Mikhail. Together, we’ve summed it up into three steps.


While urgency is critical, Mikhail feels that—given the severity of the cultural wounds within Uber—intention matters more than sheer speed:

“Being intentional about establishing culture requires you to sit down and imagine how the company would look if it were operating at its very best and then spending the time identifying the behaviours and values that are required to get there.”

Unfortunately for Dara, or for any CEO, there’s no way to achieve cultural evolution without doing the hard foundational work.

Drinking from the proverbial fire hose will only allow the fires to burn brighter.

The good news?


Example: In 2013, Ernst & Young named him entrepreneur of the year.

In this video he admits that he wasn’t a very good CEO early on at Expedia. As the story goes, eighteen months into his 12-year stint there, a young engineer said,

“Dara, you are telling us what to do. You’re not telling us where to go. If you tell us where to go, we’ll do it because we believe in you.”

Khosrowshahi credits that engineer with shifting his view of what a CEO should do.

Hmm, this sounds like someone who has experience building a culture. I don’t know about you, but I can’t imagine Travis having that same kind of reaction.


Mikhail describes it this way:

“Once a culture has been established and (crucially) communicated Khosrowshahi must embody the associated behaviours and values. He needs to make a decision to live them each day. For employees, drivers, government and the community to truly believe in the culture they need to see leadership live it.”

Earlier this year, Brad Stone published The Upstarts—a book about the cultures and CEOs of Uber and Airbnb.


Stone references the dictionary definition: an upstart is either “a newly successful person” or “someone who does not show proper respect to the established way of doing things.”

In his view, these two startups broke the mold cast by the first wave of internet companies. While leaders like Bill Gates and Mark Zuckerberg were heads-down and able to avoid the press, Kalanick and Chesky had to tackle their regulatory battles early on.

Because of that, the stakes that upstart CEOs face are much higher.

According to Stone, the most effective tech CEO in 2017 is “extroverted, a good storyteller, a politician, and someone who has the charisma to rally customers to their cause.”

Obviously, in Uber case, he was referencing Kalanick—not Khosrowshahi.

And perhaps just as obvious, it’s employees, not customers, that Khosrowshahi needs to rally right now.


Dara is inheriting a leadership team that is dramatically thin on executives—including but not limited to a CFO, COO, CMO, General Counsel, SVP of Engineering and SVP of Global Operations.

Mikhail feels that this is a unique opportunity for Khosrowshahi to hand pick leaders “whose values reflect that of the culture he is seeking to establish.” This reinforces Andrew’s initial message of cultural embodiment:

“Employing the right leaders that will, alongside Khosrowshahi, embody the newly established values and behaviours is critical to his and Uber’s success.”

So yes, hiring the right leadership team is paramount.


From my past life in corporate recruiting, I happen to know an Uber recruiter in San Francisco.

Uber has scads of open jobs in all levels, in all disciplines. And, no surprise, prospects are asking endless incisive questions about the future of the company culture.

Since it’s such a tough time to be bringing talent into Uber, I had the opportunity to personally ask Andrew Mikhail what advice he had for these potential new Uber-ites.

Naturally, his sage advice rings true not just for Uber applicants. But for anyone who is seeking a career change to a fast-growing, tumultuous organization:

Take the time to know and understand the people you will potentially work for. Don’t be afraid to ask questions, such as:

  • What is your philosophy in work and life?
  • What would you say you stand for?
  • Who has helped you get to where you are today?
  • Is there someone you have helped get somewhere they wanted to be?

The responses to those questions will give you the answers you need to make an informed decision.


Next, I asked Andrew if he had any advice for current Uber employees, who no doubt have the jitters.

He equated the feeling to his first Uber ride: That unsure sensation of jumping into a stranger’s car and trusting that you’ll get to your destination safely.

But now, Andrew is a die-hard Uber rider and looks forward to having amazing conversations with their drivers every day.

“For Uber employees, what they are going through now is no different. They might feel a little nervous, unsure and scared but by embracing the uncertainty and trusting the direction Dara is setting, theirs and Uber’s best days may well be ahead.”


The leadership lessons we’ve all learned from watching the Uber drama unfold are priceless. No doubt, as we watch the leader that is Dara Khosrowshahi come into his own, the gratis CEO training will continue.

And for that, I only have one thing to say.

Thanks, Uber, for the fascinating ride.