How quickly do you fail? The answer to that question can determine how quickly you become a great leader.
Last weekend I got the opportunity to watch my nephew ski. He’s a twelve-year-old who’s pretty athletic for his age. In the winter, most of his nights and weekends are spent on the ice playing competitive hockey around the state. Summers are spent on the soccer field playing league soccer or on the water when his dad has the chance to bring the boat out.

Conner started out as most kids do, lying on a tube being pulled around the lake when he was seven. He slowly graduated to skis and then to a wakeboard. Last summer, he perfected the slalom, gracefully making it around the lake on one ski.
He would get up on two skis and then drop one in order to slalom. His challenge this summer was to get up starting on one ski. Until this past weekend, he wasn’t able to master it.
Last weekend I received a call from my brother-in-law asking if I wanted to ‘spot’ while his kids went skiing. We went on the river that runs through our town. Being on the river makes it tough to drop a ski and find it again, so that option was out.
“Do you want to try getting up on one,” his dad asked.
“Sure,” came the confident answer, and into the water, he went.
In the next few minutes, I watched this father, Jim, effectively lead his son to victory while I received reinforcement on a great leadership lesson – failure.

On his first attempt, Conner cautiously lifted his frame out of the water while the ski yanked side-to-side. “He’s down. No, he’s got it. Now he’s down. Nope, he’s still hanging on.” For about 15 seconds, which seemed like an hour, Conner fought the ski and the resisting water until his hands slipped off the rope and down he went.
Jim pulled the boat around to him and asked, “Why’d you hang on so long?”
“I was trying to get up.”
“What went wrong?” his Dad asked.
“There was too much spray in my eyes, and I couldn’t see.”
“When did you notice that?” Jim probed further.
“As soon as I started to get up,” Conner responded.
“Well, you gave it a good fight, but ya know, the faster you fall, the faster you get to try again.”
On the next try, Conner got a little further out of the water and almost stood up, but he quickly let go on an attempt that only lasted about 5 seconds.

“What did you learn there,” his dad asked.
“If I lean forward a little, I get less spray and can see better.”
“Okay, you wanna try again?”
On his third attempt, Conner was up and heading down the river wearing a proud smile.
Conner’s father didn’t punish his son for missing the first few attempts, nor did he hold a carrot out, promising gifts if his son succeeded. Instead, Jim calmly asked questions and allowed Conner to think about his mistakes. Jim created a safe environment where failure was not seen as something to fear but something to embrace and learn from.
Very early in my career, I was asked what my greatest fear was. I responded, “Failure.” No wonder it took so long to succeed in that role. As leaders, we need to see failure as just another outcome; a deliverable less desired than the one we envisioned.
It’s the starting point for the next attempt, this time bringing the lessons of failure with us.
There are 4 great lessons that Jim helped reinforce for me:
- We rarely succeed to our standards on our first attempt. It’s in getting back up and trying a new way with the lessons of failure with us that we really succeed.
- Hanging on too long to a lost cause or a bad idea and trying to save it is just bad leadership. Fail quickly, learn, and then try again.
- Forcing ourselves to try can be the best learning experience; otherwise, we tend to shield ourselves from the unknown and hang on to old methods.
- Don’t wait until you’ve mastered a task before you try it. Mastery only comes through experience.
We’ve all heard phrases similar to “you only fail if you don’t try.” What we need to add is “You’re not trying unless you’re failing.”
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