If life is an adventure, selling in the B2B world is a race to the finish. No one knows that better than these extreme adventurers, who sell for a living and live for a challenge.

“Adventure racing is a lot like business,” says Robyn Benincasa, “small teams trying to make it through an endless series of checkpoints, moving toward a nearly impossible goal under extreme time pressure and constantly changing conditions, and all the time trying to do it better than anyone else.”

Benincasa ought to know. As a pharmaceutical rep for a Fortune 500 company, she became an Ironman triathlete, ultimately trading her business suit for a firefighter’s uniform and triathlons for adventure racing. In adventure racing, teams participate in a nonstop, no-sleep, running, climbing, and swimming competition. As a motivational speaker, Benincasa shares her experiences with business groups (robynbenincasa.com). 

“Human beings crave these chances to test themselves,” she says. “If you just walk through each day with one foot in front of the other, you never know what you’re capable of. We need challenges to help us rise to the occasion.”

“Extreme sports are a microcosm of the sales process,” agrees Jim McCormick (takerisks.com), an MBA, former chief operating officer, and sales manager who holds five skydiving records and has skydived over the North Pole. Coauthor of Business Lessons from the Edge: Learn How Extreme Athletes Use Intelligent Risk Taking to Succeed in Business (McGraw-Hill, 2009), McCormick says, “In business and sports, you have the same three steps: preparation, execution, and outcome. People like to stay in their comfort zones, but leaving [those comfort zones] is when growth comes. A manager might not take the team to the North Pole but does need to find a way to break the team members out of their self-imposed limitations.”

The secret to breaking free isn’t fearlessness; it’s focus. While simultaneously holding leadership positions in several Fortune 500 companies, Susan Ershler and her husband, Phil, became the first couple in history to climb the Seven Summits together, which means they’ve reached the summit of the highest mountain on each of the world’s seven continents. Ershler is also an author and speaker (susanershler.com), and she’s given a lot of thought to why some people give up in the face of obstacles while others persevere. “I don’t consider myself to be exceptionally gifted or unique,” she says. “In order to reach any big objective, whether it’s climbing Mount Everest or meeting a sales goal, you have to concentrate on that vision every day and prioritize around it.” 

If you’re looking for ways to inspire your sales team to new heights, consider the following lessons drawn from the world of extreme sports.

Respect the Challenge


While many people consider extreme athletes to be daredevils and adrenaline junkies, as it turns out, the opposite is true. Eric Brymer, a professor at the School of Human Movement Studies at the Queensland University of Technology, has researched waterfall kayakers, mountain climbers, and big-wave surfers and found that, in general, “they are careful, disciplined, and determined.”

Brymer continues, “To achieve a certain level in these sports, it often takes fifteen years’ dedicated training, which is not something you would associate with a thrill seeker. Even if these athletes are not able to control all the elements of their challenge – such as the weather, for example – they analyze the data and look for ways to minimize the risk.”

While researching for Business Lessons from the Edge, McCormick interviewed more than 40 “executive athletes” and found the same methodical approach. “They all respect the challenge,” he says. “Whether we’re talking skydiving or a sales call, if you don’t prepare, you put yourself at higher risk. Daredevils don’t prepare and often fail. But the people who successfully meet challenges are what I call thoughtful risk takers. They know that if they take on the challenge lightly, it will catch up with them.”

McCormick says that these thoughtful risk takers “identify the most likely outcomes and plan how they’ll respond to them. In sports, this means practicing and conditioning. In business, it’s about research and rehearsal, but either way, they come in better prepared than their competitors. How do you know when you’ve prepared enough? When you and your team can’t come up with a single contingency you haven’t addressed.” Think SEAL Team 6 prepping to catch Bin Laden: every contingency, every possibility taken into account. No shortcuts. No near misses.

Commit, Divide, and Conquer

How do you climb a mountain? One step at a time.    

“Going after a summit like Mount McKinley in Alaska can be overwhelming,” says Ershler. “I remember standing at the base of it and thinking, ‘I just want to go home.’ But my husband, who was at that time a more experienced climber, said, ‘You’re not climbing the whole thing today. Let’s just focus on what it will take to make it to the base camp.’”

Ershler says the first step is to make a commitment to the challenge, and she recalls that the first time she tried to climb Everest, the team spent 63 days on the mountain before having to turn back due to a storm. “We were obviously very disappointed,” she says, “and when I returned to Seattle, it was hard to keep up my level of training. I kept saying I was too busy. But when we signed up for a new expedition two months later, all of a sudden I began finding time to climb on the weekends. It showed me that if I wanted to climb a mountain, I couldn’t wait until I was in shape. I had to sign up for the expedition, pay my money, and work backward from there.”

Redefine “Team”

“In my motivational workshops, I do a keynote about synergy and how we all can fill in the cracks for each other,” Benincasa says, “and then we often go out into the city, divide into groups, and do a challenge that’s a bit like the TV show The Amazing Race. Despite the fact that we’ve just been talking about synergy, most of the participants immediately assume that their team is in competition with everyone else. The course is designed so that it’s impossible for one team to do all the sections, and our hope is that participants realize this and begin to share info, swap resources, and therefore score more points. In one challenge, a guy did figure out what we were going for: the task was about cooperation, not competition, and the team was really all of them, no matter what color shirts they were wearing. He stood up on the table at lunch and said, ‘Let’s split up the tasks.’ You could see lightbulbs going off in people’s heads. In the afternoon, they stopped running around duplicating efforts and easily cleared the course.”

“I know a man who always climbs by himself,” says Ershler, “but I’ve never seen the sense in it. When you get to the top, there’s no one to celebrate with. I never would have been able to climb Everest without my husband and the sherpas, and in business it’s the same way. In sales, my forte was building relationships, but I’ve never been technical. I needed to rely on others for that, to enlist and become a master of utilizing resources, working closely with these people and then rewarding them and tooting their horns when the project was over. There’s no doubt that a team can accomplish more than anyone can individually.”

Have Faith in Your Team

“Climbs are tough,” says Ershler. “You can get sick from the altitude, develop headaches, start puking. It’s up to the leader to keep people going, to motivate them to push past their perceived boundaries. Whether in business or sports, the leader’s job is to believe in people even more than they believe in themselves. You need to have high expectations of them and communicate how much you believe they can meet those expectations.”

“Leadership isn’t micromanaging,” adds Benincasa. “A leader hands out the maps and compasses and tells the team where the finish line is. But along the way there will be times when the players must find their own route and use strength and innovation to get there. Leaders show the way and convey the message that we’re going to get through this process together, but they don’t tell people what to do at every point in the journey. True leaders have faith that their team members are smart enough to figure out some things for themselves.”

Remember, It Gets Easier

The bonus of pushing yourself in one area is that your drive often transfers into another. “Public speaking is not my forte,” says Ershler, “but after climbing Mount Everest, I had this renewed sense of confidence. I thought, ‘If you could do that, getting behind a podium is nothing.’ And that’s what meeting a challenge does. You begin to think, ‘If I can run a marathon, then of course I can make that sales call.’ You begin to push yourself a little more in whatever task you’re facing.”

And eventually, exploring your limits becomes not scary, but fun. “I think people who reach the highest levels in both business and sport are those who love the roller coaster more than the merry-go-round,” says Benincasa. “High achievers are those who have taught themselves not only to tolerate but to actually enjoy the peaks and valleys.” •