Success and Short-Term Embarrassment

Suneel Gupta’s life has been transformed, for the better, by an association with failure.

Several years ago, the now best-selling author, founder of a healthcare service that became One Medical and Silicon Valley venture capitalist, received a phone call from an event planner, asking him to speak at “Fail Con” — a conference about failure.

This resulted in an article in the New York Times about failure, with a photograph of Gupta’s face illustrating the story.

“The story goes viral, and then for several months you could have googled ‘failure,’ and my face would have come up at the top of your search,” Gupta told the Gartner IT Infrastructure, Operations, and Cloud Strategies conference in a keynote address last week.

“But then someone suggested I should make it a positive, so I started to email people I hadn’t met before and say, ‘as you can see, I don’t know what I’m doing, could you give me some advice.’”

The result, he says, was some incredible conversations with a range of people, from Oscar-winning film directors to celebrity chefs, military leaders, and founders of iconic companies.

“From these conversations, I realized that when you are a leader, your job is not new ideas, but how to sell them,” said Gupta.

Hidden Step

Innovation, he said, is typically considered a two-step process: there is the idea, and then there is the execution. But these conversations showed Gupta there was a “hidden step,” which is where you get others to believe in your idea and “move people to action.”

“We make ourselves backable,” said Gupta, quoting the name of the book he has published with Harper Collins.

“That will make you a better leader, and you’ll be more effective.”

This is the first of ideas to follow in creating backable leaders.

“This is where you turn outsiders into insiders so that when your idea reaches the execution stage —you arrive together,” said Gupta.

We place up to five times the amount of value on something we build than on something we buy. Researchers call this the “IKEA effect.”

“Remember that long-term success comes from short-term embarrassment”

Finding ultimate success also means being vulnerable and open to criticism. Leaders are often required to show their ideas are bulletproof. But when they do that, they put up barriers and can give people more to disagree with.

“Instead, try lowering the guard and asking the backer what she or he thinks about one or two areas where you don’t have full certainty,” said Gupta.

“Tap into her or his expertise. When you do this, you make your backer feel like less of an outsider. Instead of hiding the holes of your idea, bring them to the forefront and use them as ‘catalysts for collaboration.’ You’ll earn trust and turn everyone on the team into problem solvers.”

Low stakes practice

The second idea was to play what Gupta describes as “exhibition matches.”

“Use low-stakes practice sessions to prepare for high-stakes moments,” he said.

“Remember that long-term success comes from short-term embarrassment. And with enough practice, you can do what Charlie Parker says is the key to incredible stage presence – ‘forget yourself and just wail.’”

To receive insightful feedback, leaders much ask specific questions.

Instead of “what do you think?” ask “what stood out to you the most?”. Or ask, “how would you describe this to a friend?”

“You might find that their description is more compelling than your original,” said Gupta.

Thirdly, Gupta’s advice is around the management of time and energy.

In growth mode, leaders can be almost obsessively focused on productivity.

They are in “constant hustle and grit mode,” which can also lead to burnout. High-performing leaders manage their time, but they also learn to manage their energy.

“Science tells us the top performers take between seven to eight mini-breaks each day,” said Gupta.

“One easy way to implement this is through the 55: 5 model. For every 55 minutes of work, take five for a focused, recharge session. As leaders, we can call for 55-minute meetings, giving ourselves and others five minutes to reset in between.”

Trusted circle

The fourth idea is networking, or “building your backable circle.”

“Backable leaders surround themselves with a trusted circle of people,” said Gupta.

“We often look for a single mentor who can coach us through all aspects of our career. Instead, surround yourself with a circle of people who can each play a different role in your success.”

These are the “four C’s:” the collaborator, the coach, the cheerleader, and finally the “cheddar,” the person who will poke holes in your idea to make you fully prepared.

Ultimately, Gupta’s message is that long-term success comes from “short-term embarrassment.”

“The most backable people in the world understand that failure is a “pathway” to success,” he said.

“But if you’re going to fail, you might as well stumble in front of your trusted circle through “exhibition matches” before the main event.”

Lachlan Colquhoun is the Australia and New Zealand correspondent for CDOTrends and the NextGenConnectivity editor. He remains fascinated with how businesses reinvent themselves through digital technology to solve existing issues and change their entire business models. You can reach him at [email protected].

Image credit: iStockphoto/Gearstd