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Why Your Team Needs to Know You’ve Failed

3 min read

This past spring I facilitated our two-day Leading with Presence program with a group of sales leaders at an engineering firm. They were boisterous, spirited, high energy, witty, and sometimes a little rowdy. They even teased each other about their socks—yes, their socks—with one participant, impish Ned, setting the tone with a colorful and whimsical pair. All that said, these sales leaders were also committed to excellence.

Their jokes and playfulness ceased, however, when Ned told his story during our storytelling module on day two. This group of talkers sat slack-jawed and mesmerized as Ned spoke. When he finished, the room was silent. Edward, a more seasoned sales professional, broke the silence: “You have got to tell that story to your team.” The rest of the group clamored in agreement.

“Oh, I know it’s a great story,” Ned beamed. “But I would never tell it at work.”

“Why not?” I asked, curious why he would pass up the chance to share such a powerful personal story.

“Because I don’t want my team to know I failed.”

Your team needs to know you failed….once

Usually, when a participant tells me they won’t use the story they’ve crafted in our training in an actual work setting, it’s because the story feels too vulnerable. Maybe it’s about the death of a family member, or fleeing war and violence in their home country, or even a touching moment with a young child. And, usually, with some gentle prompting from me and the other participants, they see the value in being vulnerable and decide to tell their story in a work setting.

But, Ned’s story wasn’t tender or sad or horrific. Early in his college career, he had miscalculated the exact ratio of study time to party time, and the miscalculation had just about cost him his spot in the engineering program until he made some different—and better—choices. He turned himself around, graduated, and had been a high performer ever since. To me—and his colleagues—this story felt, well, highly relatable.

Moreover, Ned’s story gave us some context for his management style. Even with his quick jokes, big smile, and zany socks, Ned pushed his team hard and expected the best. With this story of failure, we could understand how he became that way. He knew the true cost of goofing off, so when it was time to get down to business, he wanted his team to work hard.

When you as a leader or manager choose to tell a story about a time in your life when you failed, it impacts your team on a number of levels. First, the story humanizes you and makes you seem approachable and relatable, instead of some flawless idol on a pedestal. Second, the story imparts genuine learning (more on that below). And third, such a story builds trust and connection with the audience because we are vulnerable when we share our struggles, and that vulnerability builds connection.

How to craft a story about failure

When I was in my graduate program in education, we discussed the cruel irony that we only ever learn through failure, yet schools typically punish us for failing. This paradox inspires me as facilitator to create safe learning spaces where my clients and participants can try something out, not do it perfectly (and that’s okay), and try something different to have a more desired impact. I truly believe that we learn through mistakes—there is no other way.

1. Reflect on the key learnings in your life

To craft your own personal story about a mistake or failure in your life, start first with what you’ve learned. Behind the big learnings in your life are your big failings. What are your values? What are the biggest lessons you’ve learned in your life? I can almost certainly guarantee you that you learned those lessons “the hard way.”

2. Beginning, middle, and end

Take that lesson and piece together the story of how you learned it. Boil complicated scenarios down to their essence to keep the story crisp and use tactics like “fast forward six months later” to manage long timelines. Have a clear beginning, middle, and end, and use short sentences and pauses to build suspense. Challenge yourself to tell the story (including what you learned) in two minutes. Yes, it can be done.

3. Bring your story to life with details and expressions

You’re not simply narrating a moment in your life; you’re trying to connect with an audience. Use key sensory details to paint the picture for your audience. What was the weather like? What sounds did you hear? Could you smell anything? Gestures, facial expression, and changes in your voice help to set the emotional tone for your story. Stretch yourself!

4. Practice, practice, practice!

To paraphrase Mark Twain, it takes weeks of rehearsal to appear spontaneous. Practice telling your story in front of the mirror or even in front of a trusted colleague or friend. Ask for specific feedback on things like being succinct, pausing, having a clear message, and being expressive.

5. Don’t be afraid to fail

Enough said.


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