Failure is an option

When my children were young, I realized that teaching them how to lose was every bit as important as encouraging them to put their whole selves into winning. Whether their first baby steps, swinging a baseball bat, trying an advanced math class or acquiring a new skill, only through failure did they eventually master their successes.

Losing and failure are one and the same, teaching us all compassion, grace and the way forward — vital lessons for young minds, as well as for leaders.

Failure is a tremendously powerful teacher. In fact, successful people fail early and often before they go on to soar. Accepting this and teaching an understanding of this principal are the responsibility of every leader.

Encourage and understand

Jeff Bezos, one of the world’s most successful businessmen, talks about failing early and often. He believes failed experiments are prerequisite to successes, calling them “inseparable twins.” Bezos embraces, and even encourages, failure, which is woven into Amazon’s culture.

To exhibit this, a friend used a fun way to demonstrate to a high potential, but somewhat timid colleague that it is OK to fail. Giving her three get-out-of-jail-free cards gave this team member the freedom to try new things and to grow. She used all three in a span of six months, but her initiative grew leaps and bounds, as did her contributions to the organization.

Be bold

Wise leaders embrace the risks associated with the rewards and use failure as teaching moments. Bezos also says, “Nine times out of 10, you’re going to fail. But every once in a while, you’ll hit a home run.” Most organizations encourage invention but too often don’t realize or cannot tolerate the chain of failures needed to fulfill the promise that invention can yield.

When failure is an option, the rewards — when they come — are ever so much sweeter.

Gain perspective

The best leaders have an entirely different, perhaps unconventional, view of failure. Thomas Edison once said, “I haven’t failed. I just found 10,000 ways that didn’t work.” He only had to find one way to make a working light bulb out of those thousands of failed attempts. It’s all in how you look at it. He also stated, “Many of life’s failures are people who did not realize how close they were to success when they gave up.”

Evolve the culture

Bezos says, “Failure comes part and parcel with invention. It’s not optional. We understand that and believe in failing early and iterating until we get it right.”

Sometimes leaders and teams want to get every little thing in place before trying an idea. In the rapidly changing landscape, this is often impossible to do quickly. Explicitly talking about embracing failure as a part of the culture is a leader’s responsibility, as is an emphasis on recognizing what knowledge or skills were gained through the process.

Will Smith put it a little differently in a YouTube video: “Fail early, fail often and fail forward.” If leaders only allow for things that are proven to work, opportunities may be missed.


Aradhna M. Oliphant is president and CEO of Leadership Pittsburgh Inc. LPI strengthens regional leadership by connecting current and emerging leaders and high-potential veterans with each other and with people and issues that shape communities. Under her leadership, demand for LPI programs has grown exponentially. A graduate of LPI, Aradhna is deeply committed to the region including through service on boards and commissions. She is invited frequently to speak and write on leadership.