How to Drive Your Business Off a Cliff (or Be an Amazing Leader Instead)



As the head of a multi-billion-dollar tech company, Uber CEO Travis Kalanick is in over his head.

For years he delivered explosive growth to his investors. He took an unknown concept – hailing a ride through an app – and spread it across the globe. After making Uber a household name, the company began disrupting other industries.

And yet, like so many cautionary leadership tales, how Travis Kalanick managed to achieve these exceptional results is now the subject of legal and ethical challenges. His win-at-all-costs approach – whereby he flouted safety regulations, capitalized on legal loopholes, and engaged in other questionable practices – has caught up with him.

Former U.S. Attorney General Eric Holder, who once advocated on Uber’s behalf, is now leading an investigation into allegations of sexism and a range of management issues. Company president Jeff Jones has stepped down, citing irreconcilable differences with “the beliefs and approach to leadership” at the company. #DeleteUber has become a movement that has so far cost the company 200,000 riders.

What’s Going On?

I’ve never met Travis Kalanick. So I wouldn’t claim to know the inner workings of his mind. From the outside, though, he looks like plenty of leaders I do know. People driven by ambition, or fear of repeating past mistakes. People who hurt those around them, and either don’t notice, or don’t care. People who “rose to the top” so quickly, their business success eclipsed their dangerously lagging level of maturity. People who haven’t paused in the last decade to reflect on themselves as leaders.

Kalanick likely believed he was a great leader, that his critics “didn’t get it.” He wouldn’t be the first. Maybe colleagues and friends gave him feedback over the years – that he was too cavalier toward his workforce, for example — but he shrugged it off. Maybe he felt too busy, too important, or too strong to engage with the so-called “soft side” of leading.

What’s clear is that for a while his business results were too impressive for questions about his leadership style to matter enough to him or to other stakeholders, such as Uber’s customers. Yet, like many leaders I advise, this looks like an influential person with off-the-dial horsepower, who somewhere along the way to corporate stardom lost track of himself.

How to Avoid the Cliff? or Seek the Extraordinary?

In an opinion piece last week, political commentator David Gergen wrote of the current occupant of the White House, “he needs to see and embrace a central idea for anyone running an organization: leadership starts from within.” I can’t agree more.

For anyone with authority, your capacity for extraordinary leadership rises and falls on your ability to lead yourself. This principle applies equally when you want to steer clear of an embarrassing fail as when you aim to create remarkable results.

Kalanick himself has now heard the wake-up call. Posting a public apology in late February, he wrote “I must fundamentally change as a leader and grow up. This is the first time I’ve been willing to admit that I need leadership help and I intend to get it.” We all need leadership help. Paradoxically, though it might have made him feel weak, asking for help in this crisis is a sign of strength.

One of my passions is to capture and return lost wisdom to leaders. In today’s world, we’re largely cut off from centuries of teaching about the nobility of leadership. In turn, our leaders aren’t living out their true heroic nature. They’re chasing something, but that’s different from pursuing the quest of your life.

Watching Uber implode these past few weeks highlights the consequences of knowing your business but not knowing who you are. The latter requires you to step back and ask bigger picture questions, at a time and place where you can notice hints pointing you in the right direction. Extraordinary leaders understand this.

What are “bigger picture” questions? What should you do if you feel curious about asking them?

Sometime in the next 2 weeks, set aside a quiet hour when you can sit by yourself. Get a pen and some paper. Yes, I know you have your phone or tablet or laptop. But tapping into deeper currents works better when you take a pen in your hand. Trust me.

Yes, you’re busy, and you can also think about these questions while you drive your car to work. Again, trust me on this. You need to tap into a different part of your intelligence. Think and drive means you’re just thinking. Like you always do. Not going to lead to new ground.

Then choose one of these questions, or any ones that come to mind, and without thinking about it, just start writing. As best you can, keep writing without stopping to think through your next thought. Knowledge resides in our intellect: inner wisdom often comes from somewhere else. At a minimum, don’t read over what you’ve already written, and start editing it. Just keep moving forward.

Stop when you feel complete. Leave the pages in a private place. Come back later (an hour? A week? that’s up to you), and review your notes. Then pick a new question and start again. Some questions elicit a “yes or no” answer. Don’t stop there – elaborate. What do you mean when you say “yes” or “no”?

If you do this practice for a few weeks, or months, at some point you sit back and quietly, slowly, read everything you’ve written. You’ll be surprised at the insights you discover simply by truly listening to yourself.

Here Are 10 Sample Questions:

1)   Aside from my job and the roles I play, who am I?

2)   What is the purpose of my life?

3)   Is my life aligned with my purpose?

4)   What quest am I on?

5)   Who are my guides? If I can’t think of any, who could I enlist to help guide my way?

6)   How do I know when I’m lost?

7)   Who are my allies who show me I’m getting lost, and help me find my way back to my quest?

8)   What fears do I need to face to move forward?

9)   What, if anything, am I running from?

10)   What, if anything, do I have to prove? To whom? How will I know when I’ve proven it?

Don’t sit in the back seat of your own leadership. Don’t drive off the cliff. Seek the heroic quest of your life, and then live it. Choose the road to extraordinary.

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