Many times I wish I was a fly on the wall. Like in Kennedy's quarters during the Cuban Missile Crisis, or in the Knowles house after Beyoncé learned of Jay-Z's transgressions.

I'd now add during a secret meeting between two titans of industry, a meeting recently disclosed by the New York Times.

It was one for the ages because Uber CEO Travis Kalanick got taken out behind the woodshed by Apple CEO Tim Cook. Cook threatened to take the Uber app out of the Apple App Store (a fatal blow).

Why?

Because Cook became aware of a ludicrous risk that Kalanick took, one that violated Apple privacy policies.

Turns out Uber had been combating account fraud, where unscrupulous drivers would buy stolen iPhones and hail and accept rides from the phones to increase earnings. To stop this, Uber engineers had been tagging iPhones with code to give it a permanent identity, a practice known as "fingerprinting" (and against Apple policy that a wiped iPhone should leave no trace of the former user's identity).

But the plot thickens.

Inconceivably, Kalanick had his engineers geofence Apple's Cupertino, California, HQ--a way to digitally see who on Apple's team was reviewing Uber's software, and then obscure the fingerprinting Uber was doing.

The high-tech hi-jinx got spotted though by Apple engineers outside the Cupertino area, leading to the Cook v. Kalanick showdown.

Kalanick has a track record of taking outrageous risks that have disregarded regulatory rules, exploited legal loopholes, or promoted questionable competitive tactics.

Despite all this, I'm not encouraging you not to take risks.

Kalinick's methods are way out of bounds, no question. But nobody can question the man's passion for the fact that the biggest risk is not to take any.

He exemplifies risk gone too far, but what about risk-taking in general?

The truth is, an equally big Travis-ty (see what I did there?) is happening in companies across the country on this front.

A study conducted by Blessing White found that 41 percent of employees said their manager never encouraged them to take risks, while another 33 percent said their manager only sometimes encouraged them to take risks.

The vast majority of us work in a culture of caution, versus courage.

Yes, I'm using an example of a ludicrous risk to encourage you to take more risks in general--to be inspired by the passion Kalanick has for risk-taking while rejecting the way he plays that passion out.

Here are 5 ways to encourage more risk-taking gone right:

1. Get clear on the rules of risk-taking

Risk-taking seems scary because we don't understand the "rules of the game". Find out what they are by asking questions like, "What constitutes a smart risk or a dumb one?", "Who needs to approve a risk?" "What happens in the face of failure or success?".

Frame your questions as wanting to understand the rules of risk-taking. This initiates conversation in a non-threatening way and illuminates degrees of freedom you have.

2. Start a small brush fire

We're often faced with a conservative chain of command that doesn't value, reward or even punishes risk-taking.

Change attitudes towards risk-taking by starting small and slowly fanning the flames. Request to do some experimentation, just to get risk-taking more familiar and in the DNA of the place.

Be clear on the business case for the experiment and set clear rules, budgets, and timelines. Celebrate and share the results if the risk pans out, and if it doesn't, be enthusiastic about what's been learned, talking about it to management as a process of paying tuition.

3. Create risk pools

Form a small cluster with peers and get empowered to take risks. The common experience of navigating unchartered territory will yield bonding, a spirit of figuring things out together, and will improve the chances of success. The shared experience will make risk-taking less scary.

4. Get the math right

Research indicates that we consistently overestimate the consequences of taking a risk, while we discount the cost of status quo. So be realistic in your assessment of what can go wrong and the associated pain, including an honest assessment of whether or not what could be lost is in truth superficial.

5. Think of risk-taking as a skill that must be built

No different than visioning or strategic thinking, risk-taking is an essential skill required for success.

Sara Blakely, the billionaire founder of Spanx, says she learned to appreciate the value of risk-taking because her dad asked her and her brother the same question every Friday at dinner - "What have you failed at this week?" (I, instead, was asked, "What haven't you failed at this week?")

So let Uber's passion (not practices) for risk-taking inspire you to uber success.

Published on: May 4, 2017
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