How Leaders Can Survive the Dangers of 'Uber' Success

Failure is painful, but at least starting over is straightforward. Big success can be bewildering.
How Leaders Can Survive the Dangers of 'Uber' Success
Image credit: Chris Ratcliffe | Bloomberg | Getty Images

It’s been a tough year for Uber -- executive resignations, accusations of unaddressed sexual harassment , the massive Waymo lawsuit and, of course, February’s YouTube video of CEO Travis Kalanick berating one of his own drivers. 

The usual response is to frown at Kalanick’s missteps, post a few emoji-laced reactions, and move on.

In truth, Kalanick is far from an aberration. For leaders -- especially those who experience high-profile, uber success -- winning can be far more damaging than failing. “The most dangerous poison,” said Swedish billionaire Ingvar Kamprad, “is the feeling of achievement.”

The only way to overcome the dark side of success is to face its challenges head-on.

Related: 11 Qualities of Super Successful People (Infographic)

Stay sensitive to problems.

In the wake of success, hubris descends. Where responsiveness to small problems was once acute, pride numbs us. Believing our own hype is just one symptom. Feeling invincible -- what Harvard Business Review calls “overconfidence bias” -- is far more precarious. Rather than deal with issues as they arise, we ignore or brush them off as something we used to worry about, but not now.

Unfortunately, success not only amplifies old problems, particularly those left unaddressed, it also brings along a host of new ones. Struggles with customer acquisition are compounded by service and retention. On top of marketing and sales come 3PLs, supply chains and distribution. And while chasing PR consumed your time prelaunch, figuring out who to say no to becomes its own burden.

The good news, as Merchant Machine founder Ian Wright told me, is that “leading a thriving business is not necessarily about being a polished perfectionist or having years and years of experience already behind you. It’s more a matter of evolving with the enterprise as it grows.”

In other words, the solution to old and new problems isn’t to have all the answers. The point is to know you don’t. Sensitivity, curiosity and humility are far more vital.

Related: Why Business Is Not Just About Dollars

Create a culture of accountability.

It’s a leader’s job to not only establish goals and boundaries but let others know when they’ve crossed the line. Just as pride clouds us as individuals, so too it clouds organizations.

As Nicole Cuellar, an operations and logistics manager at Uber, explains: “For the first several years, we had to just focus on executing our operational goals, and that was kind of the be-all, end-all. There was never the need to think about our culture like that. And I don’t think it sunk in until we all had this really gut-wrenching experience.”

Launching a brilliantly designed product is one thing. Keeping it on a steady course and navigating the inevitable rocks is another. In the words of LinkedIn Youth Editor and recipient of the UN’s Outstanding Youth Leadership Award, Manu Goswami, “Creating a culture of accountability means connecting every facet of the overall system, from operations to HR to marketing. A healthy dialogue between all departments can ensure that employees feel part of a bigger mission.”

Communicating a vision beyond growth, and holding others responsible, is uncomfortable work. But it’s one of the few ways to fight back against the entitlement success brings with it.

Get brutally honest feedback.

Naturally, the bubble of success envelopes more than our own minds and organizations. Outsiders -- both known and unknown -- are quick to supplement our egos with accolades. Not all feedback is created equal.

Speaking truth to power is difficult. Speaking truth to success, even more so. Much of Uber’s recent criticism has surrounded the “bro culture” endemic to Silicon Valley. A Dan Lyons New York Times article explains, “A ‘bro co.’ has a ‘bro’ C.E.O., or C.E.-Bro, usually a young man who has little work experience but is good-looking, cocky and slightly amoral -- a hustler. Instead of being forced by investors to surround himself with seasoned executives, he is left to make decisions on his own.”

A number of years ago, Circuit Court Judge and Brigadier General Dan Bunch spoke to one of my college classes. “There are three phrases,” he said, “you want to hear from the people who really care about you: ‘Stop it. You suck. But we can fix that.’”

In business, finding people who love us enough to give brutally honest feedback should be a top priority. This means going against the grain of both our egos and most leader’s own optimistic bend. Pessimists, naysayers, and -- most of all -- critics should be our closest teachers.

Related: Tell It Like It Is: Radical Candor Is the Feedback Method Your Startup Needs

Overcoming success.

While Kalanick’s future is uncertain, Uber show no signs of slowing down, at least when it comes to growth. However, rather than pass judgment on a CEO who’s beginning to look more and more like Icarus, let’s learn from him. Sensitivity to problems, a culture of accountability and brutally honest feedback are three ways we can ensure that success doesn’t become an invitation to failure.

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