Posted On: Monday, 25 May 2015 by Rajiv Popat

We live in a culture that celebrates success.

If you want to understand how biased we are  towards success, ask a few candidates you interview these two questions and watch their enthusiasm take a nose-dive after sky-rocketing as they go from answering question one to answering question two:

  1. What were your three biggest achievements in your current organization?
  2. What were your three biggest failures in your current organization?

There is nothing inherently bad or demeaning about failing and yet every time people have to talk about their own failures they either go completely silent or go out of their way to sugar coat their responses. They edit the stories of their failures to either end with it wasn't my fault - or end with - things were out of my control.

But as a culture are we undermining the art of failing and in doing so missing out the remarkable outcomes well planned timely failures can create?

In his book Little Bets - How Breakthrough ideas Emerge from Small Discoveries, Peter Sims talks about the art of failing and why the art is so important:

Chris Rock has become one of the most popular comedians in the world and, while there is no doubt he has great talent, his brilliance also comes from his approach to developing his ideas. The routines he rolls out on his global tours are the output of what he has learned from thousands of little bets, nearly all of which fail.

Peter goes on to describe how Chris picks local small comedy clubs to practice his routines when he starts working on material for a new show. Peter describes how Chris goes from one local comedy club to another trying out new ideas and jokes most of which fall flat on their face and fail miserably:

In sets that run around forty-five minutes, most of the jokes fall flat.  His early performances can be painful to watch.  Jokes will ramble,  he'll lose his train of thought and need to refer to his notes,  and some audience members sit with their arms folded, noticeably unimpressed.  The audience will laugh about his flops laughing at him, not with him. Often Rock will pause and say, "This needs to be fleshed out more if it’s gonna make it" before scribbling some notes.

He may think he has come up with the best joke ever, but if it keeps missing with audiences, that becomes his reality. Other times, a joke he thought would be a dud will bring the house down. According to fellow comedian Matt Ruby, "There are five to ten lines during the night that are just ridiculously good. Like lightning bolts.  My sense is that he starts with these bolts and then writes around them."

What Chris Rock is doing is practicing the art of arriving at success through failure. Chris is failing early and he is failing often so that he would not have to fail on the big event in front of millions of people. Chris like most others who are really good at what they do has mastered the art of dissecting and analyzing his failures. Chris has mastered the art of listening to the stories his failures tell him and learn from those stories.

In his article Malcolm Gladwell talks about a similar method to find out how good surgeons really are:

Charles Bosk, a sociologist at the University of Pennsylvania, once conducted a set of interviews with young doctors who had either resigned or been fired from neurosurgery-training programs, in an effort to figure out what separated the unsuccessful surgeons from their successful counterparts.

He concluded that, far more than technical skills or intelligence, what was necessary for success was the sort of attitude that Quest has—a practical-minded obsession with the possibility and the consequences of failure.

"When I interviewed the surgeons who were fired, I used to leave the interview shaking,” Bosk said. “I would hear these horrible stories about what they did wrong, but the thing was that they didn't know that what they did was wrong. In my interviewing, I began to develop what I thought was an indicator of whether someone was going to be a good surgeon or not. It was a couple of simple questions: Have you ever made a mistake? And, if so, what was your worst mistake?

The people who said, 'Gee, I haven't really had one,' or, 'I've had a couple of bad outcomes but they were due to things outside my control'—invariably those were the worst candidates.

And the residents who said, 'I make mistakes all the time. There was this horrible thing that happened just yesterday and here's what it was.' They were the best.

They had the ability to rethink everything that they'd done and imagine how they might have done it differently.” - What this attitude drives you to do is practice over and over again, until even the smallest imperfections are ironed out.

The interview question isn't just for surgeons. It works for programmers (and most other fields) too. The old proverb that 'failures are pillars of success' is such a cliché. Your failures by themselves say nothing about your success; but they do tell a story that can take your life from the bad side of the line of best fit to the side where amazing outliers sit.

How intently you listen to the story of your failure and learn from it, decides which how quickly you shape a successful story of your work-life. So go on, fail early, fail often. Then reflect on and listen to the stories of your failures (both big and small) and use these to write the story of your success.

Oh and the next time you have to tell your stories of failure, be bold, be open, be unashamed and be elaborate because that will tell us that you're intently listening to and learning from the stories your failures tell you and that, is a good thing.


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