Why Ask Why

If you want a high-performance team, you need each team member to know what they’re doing and why they’re doing it. And you need to know that as well.

Adventure athlete Jason Caldwell has become an expert at building successful teams. In 2017 he assembled a four-man crew that broke the world record for the fastest crossing of the Atlantic Ocean by rowboat. In 2021, he broke the record for crossing the Pacific Ocean by nine days. However, these records were only possible because of the lessons he learned from his first failed attempt.

In 2016, Caldwell built a team to enter the Talisker Whisky Atlantic Challenge, widely considered to be the “world’s toughest row.” His chosen teammates were some of the strongest rowers in the United States. They were physically talented, but when a crisis threatened on the ocean, not all were adequately motivated to finish the mission. One team member chose to quit just 600 miles into the 3,000 mile race, taking any chance of victory with him. It was a disaster Caldwell could see coming from the beginning.

Caldwell’s team finished the four-man race with only two men left in his boat. Nick was rescued after falling gravely ill, while Ethan chose to abandon the team, no longer willing to suffer to finish a race they could no longer win. 

“The most serious mistake I made was thinking strong rowers would automatically become a strong team, that just sharing the same space and the same heading would make us a team.”

What Caldwell lacked on that first attempt to cross the ocean was a deep understanding of why each man wanted a seat on the boat. While Ethan showed initiative from the start, reaching out to Caldwell out as soon as he heard about the team he was forming, Caldwell eventually realized his motivation wasn’t enough to sustain him on the ocean for 30 days. Ethan wanted to be part of the first American team to ever win the Talisker, but as soon as that was no longer possible following Nick’s illness, he had no reason to stay in the boat regardless of Caldwell’s intention to continue the race.

Looking back, Caldwell said, “I knew he wasn’t right for the team from the day I recruited him. I saw how he interacted with the other team members, and it wasn’t good. But I didn’t care. He was a good rower, a great rower, even. And I wanted to win a rowing race, so Ethan stayed on the team.” 

In contrast, Tom was exactly the kind of teammate Caldwell needed to finish the race. Despite being the weakest rower of the four, he was “adaptable and the most connected.” He could have easily quit after the departure of Nick and Ethan, but he chose to stay because finishing the race was important to Caldwell, and Caldwell was important to Tom. There was a deep, personal loyalty that motivated Tom. Though the mission changed from winning the race, now to simply finishing, Tom was unmoved. Caldwell took note, he would no longer take his teammates’ motivation for granted.

During our last basketball season, we were fortunate to have Jason Caldwell spend an hour with our team before we entered the postseason (you can listen to our conversation HERE). He talked about this leadership lesson, and it prompted a fascinating discussion on our team afterwards.

Your why's don’t have to be the same, you just have to know what each other’s are. You need to help each other achieve those. We want there to be alignment between the team goal and individual goals. We want to make sure everyone is getting what they want individually while the team is still going toward their desired outcome.

Understand yours. Be honest with yourself. What do you really want out of the team you're on? You should know other people’s why's.

While I have known intuitively that everyone is motivated differently, we’ve never asked that question specifically or had players share their why with each other. I had no idea how diverse their answers would be. Here’s what they said:

  • I think it’s because of my parents, but it could also be wanting to be with this team.
  • To play with my friends. Be around a supportive group of people. See where my basketball career takes me.
  • I owe it to my fellow seniors to come everyday and give it my best. I feel an obligation to my family. Be with some of my favorite people every day. Make connections with people I don’t normally see. Goals I want to accomplish. 
  • Building friendships. The competitiveness. Enjoying the sport. The good memories the sport has given me. 
  • I love playing with the people on this team. They make it exciting every day.
  • Basketball offers fun experiences and memories that I am thankful to be part of.
  • Get another shot at our rivals and go to State. Play with the seniors and my friends one more time.
  • My teammates and the culture we share as a team. Seeing my best friends every day. Good laughs and funny moments. Being on a competitive team where everybody wants to get better.
  • Feel like I’m part of the team. I feel like I’m part of this one even if I have to contribute in different ways. 
  • My why is that I love the sport and I love my teammates. No one on this team has a selfish mentality, and we all play for each other. We are always having fun and are really supportive of one another. I’ve also played basketball my whole life, and couldn’t imagine not playing the sport.

Perhaps the most powerful part of that conversation was the realization that every one of us has a different reason for being - a unique set of aspirations and motivations - yet we were all committed to the same goal. That moment brought our team even closer together.

Like Caldwell, the question of why is one we will no longer take for granted. It allows us to know our players better, and allows them to connect on a deeper level with each other. It’s a question we will ask repeatedly over time as our motivations can change as our circumstances change.

Take a look at your roster. Do you know what each player really wants out of their experience with the team? If you’re not sure, it’s time to ask.

Food for thought.


For those interested in hearing more about Jason, you can listen to our conversation with him on the Coaching Culture Podcast here:


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