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3 Things Failing Miserably Teaches You About Leadership

Skip the painful process of falling flat on your face, and learn these important lessons from one CEO who has stumbled badly.
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You've no doubt been told countless times to stop fearing failure and accept it as a growing experience and precondition of innovation and accomplishment. It's a popular mantra, but in a world filled with corporate CYA and zealous reputation management, examples of it in practice are pretty light on the ground. But there is one standout example: meet James Altucher.

A serial entrepreneur who has started 20 companies (17 of which failed), Altucher has built a massive following by admitting in detail all the incredible ways he's screwed up. But reading Altucher's work isn't all about reveling in another's missteps. He's also a generous giver of advice on what all that failing has taught him.

Take, for example, a recent in-depth answer he wrote to the question, "What is the most important thing you have learned about leadership?" on question-and-answer site Quora. In his response he once again admits his shortcomings. "They fired me as CEO. Then they fired me as a board member," he writes. "The reason? I was a bad leader. Here are some things I didn't know about my own company: I didn't know what our product did. I didn't know any of the clients. I didn't know how much money we made. I didn't know how much we lost. And I had crushes on the secretaries and maybe two or ten other employees."

But he doesn't stop there. Altucher also goes on to share what his failure actually taught him about leadership, offering up 10 lessons he took away from these experiences. That's handy as a practical illustration that all those touting the educational value of failure might be on to something, but better yet, it offers entrepreneurs hard-won knowledge without actually having to walk Altucher's painful path. Here are a few examples:

1. Yes, and...

Saying no is easy. Far more difficult than shooting down ideas is encouraging creativity and drawing out better ones. In order to do this you need to take a page from improv comedians and learn to tame your knee-jerk, "No!" response to innovative suggestions. You need to get better at fielding ideas and improving them. You need to develop the habit of responding with "Yes, and..." Altucher lays out his bullet-pointed suggestions for a better way to give constructive criticism:

  • "Yes, and"
  • List what's good
  • How you would improve
  • Figure out the vision that is the base of the idea that you are talking about.
  • Connect the "Why" of what you are suggesting to the initial vision. Does it work better than the initial idea?
  • Be open to the fact that you might be wrong. ALWAYS ALWAYS you might be wrong.

2. Be the Storyteller-in-Chief

There are limits to how many people any individual human can build meaningful connections with (your 600 Facebook friends notwithstanding). Altucher calls this the 30/150 rule: below 30 people you're a tribe; from 30 to 150 you can know of everyone by reputation at least; after 150 forget about personal connections entirely. So what ties together organizations as they grow past this 150-person barrier? Stories.

"We united with each other by telling stories," Altucher writes. "If two people believe in the same story they might be thousands of miles apart and total strangers but they still have a sense they can trust each other." Leaders need to leverage this truth by telling visionary stories such as "we are delivering the best service because... We are helping people in unique ways because... A good story, like any story ever told, starts with a problem, goes through the painful process of solving the problem, and has a solution that is better than anything ever seen before."

When you're past the point of listening to and taking care of every employee individually, telling these sorts of unifying stories is essential for a leader. "Companies live and die on this," Altucher insists.

3. Lead Yourself

Altucher isn't the only leadership expert who makes the incredibly essential but all-too-frequently overlooked point: You're unfit to lead others until you're pretty good at leading yourself. So before you develop lofty aspirations of guiding others, make sure you've done the necessary work on yourself.

"Before I can lead anyone I have to lead myself. I have to read. I have to try and improve one percent a week. I have a handful of interests and I have a lot of experience. I have to get better at the things I'm interested in. I have to understand more deeply the painful experiences I've had, I have to every day practice the health: physical emotional mental spiritual, that I suggest to everyone else," he writes.

What leadership lessons have you taken away from your failures?

Last updated: Aug 6, 2014

JESSICA STILLMAN

Jessica Stillman is a freelance writer based in London with interests in unconventional career paths, generational differences, and the future of work. She has blogged for CBS MoneyWatch, GigaOM, and Brazen Careerist.




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