What if you pretended that failure didn’t exist? A review of Robyn Benincasa’s book ‘How Winning Works: 8 Essential Leadership Lessons From the Toughest Teams on Earth’

Book review by Laura Soule

How Winning Works
How Winning Works

Early on in her book, Robyn Benincasa illustrates the similarities between adventure racing and the business world. There are “…teams of men and women working together, struggling through a series of seemingly endless check points, searching for a nearly impossible finish line, in constantly changing conditions, operating under ridiculous deadlines, with each team trying to do it better than any other team in the industry…”

It is so true – especially the part about the nearly impossible finish line.

Many great books and courses on leadership center around some basic tenants, such as:

1) Share the credit
2) Show that you care about something other than numbers
3) Be respectful to all employees, regardless of rank
And so on…

But Benincasa, through the lens of adventure racing, revealed some nuances to these rules that are a little less obvious. Some of them surprised me, in fact. You could almost call these insights the ‘hidden treasures’ of business relations. I don’t want them to remain hidden!

How Winning Works is unique among the business leadership books in that it features remarkable stories of people enduring dangerous and physically-exhausting challenges – the kinds of things most of us will likely never experience. Yet, Benincasa makes us feel like we are right with her as she contends with angry wasps, hypothermia, waterfalls, trench foot, freezing temperatures, and towering ocean waves. (I can guarantee that the unfortunate scene involving an illness in a kayak will stay with you. Luckily, the story ends happily – amazingly happily, in fact.)

But it is also one of the more inspiring reads in that it paints such vivid pictures of all-out optimism, indomitable spirit, helpfulness, and good ol’ fashioned ‘menschness’ that it just might make you sit up and say ’Now that’s the kind of person I want to be!’

Here are a few of the insights that really resonated:

Know what it really means to care
We are told how important it is to learn who our teammates are as people. But it is a different thing to really see things from their point of view, understand their struggles, and be willing to lend a hand. Do you truly care about your teammate or are you concerned with them only as they relate to your own goals? The bottom line is, if you’re self-centered, you’re doomed.

Carry someone’s backpack
We all have some grasp on the differences between constructive criticism, unsolicited advice, and micromanaging. The art of truly beneficial coaching can’t be covered here, as that topic is too complex.

But Benincasa shows us another method of interactive problem-solving that begins with a simple question: How can I help? This not only encourages a person to open up and communicate but also shows your respect for their expertise. Share the suffering as well as the picnics. If you’re feeling pretty good about how things are going, then maybe you should lighten the load for someone else who is struggling.

Keep on the sunny side (especially when you don’t feel like it)
Attitude is another theme in discussions about business and productivity. We know that a good attitude is important. But take that concept even further — what if you pretended that danger and failure didn’t even exist?

Benincasa shares stories about some of her Australian and New Zealand teammates, whom she depicts as the most impossibly positive people you could ever meet. These are the kind of folks you’d really want on your team. In what she calls the ‘Kiwi and Aussie way’, nothing was ever truly lost. In fact, she sees this wildly-confident outlook as a secret, problem-solving weapon: “Confidence begets hope and hope is what keeps us mentally in the game to brainstorm solutions.”

There can be a certain comfort and routine in having a clear pecking-order and chain-of-command. In the best of cases, a hierarchy helps ensure an appropriate and efficient division of labor. In the worst of cases, a hierarchy decrees ‘who is allowed to talk to who’ and gets in the way of productive work.

Benincasa is quick to point out the shortfalls of a too-severe hierarchy. As she illustrates, adventure racing doesn’t mix well with a top-down leadership style because plans constantly change and no one person can be an expert. The dynamic conditions demand what she calls a ‘kinetic’ leadership system where members take turns leading depending on the situation. Also, this allows different leadership styles to emerge when needed.

If you think about it, the world of business is changing so fast that maybe the rotating-leadership method has many advantages. What really makes this system work, though, is absolute trust and respect among ALL team members.

Revise the finish line
When I started this book, I wondered how Benincasa was going to address the dreaded concept of ‘failure’. What happens when defeat is inevitable?

And the answer is: Just avoid losing altogether!

What? How?

Easy – By rewriting the goal!

How Winning Works shows us how great leaders will reframe what a ‘win’ looks like in order to keep the motivation high among their teammates.  This could mean creating a new goal or shifting the focus towards something else altogether.

It is clear that leaders who ‘reframe and refocus’ are trying to keep a vicious monster at bay: the one named Disappointment. We’ve all seen how disappointment in a workplace can affect people’s moods, attitudes, and even their abilities. Not only does it spread like a virus, but it can breed all kinds of other nasties such as blame, fear, and demotivation. Benincasa shares examples of how the wrong mindset can wreck an otherwise highly-talented team, and how the right one can keep a crippled team pushing on over the finish line.

We tend to look at ‘winning’ and ‘losing’ in very stark terms, likely because we are so used to snap judgements made by the public and the media. This is where overcoming our ‘lizard brain’ tendencies becomes tremendously important. How you communicate to your team and how you keep them motivated is just as important as the story you tell externally. The naysayers and critics won’t go away. (And, besides, they can’t help themselves.) But the story is still yours.

It is rare to find an entertaining leadership book that also doubles as a travelogue. Plus, How Winning Works might help you refine all of your interactions – both inside and outside of work. Happy reading!

Robyn Benincasa, world champion eco-challenge adventure racer, CNN Hero, New York Times bestselling author, founder of the 501c3 Project Athena Foundation (Survivors to Athletes!), and full time San Diego firefighter inspires people to grab life with one hand, grab their teammates with the other, and to create that special magic that makes all of us better together than we ever would have been alone.

Robyn is the keynote speaker at the Healthcare Businesswomen’s Association 2015 Annual Conference to be held November 3- 5, 2015 at the Marriott Marquis in Atlanta.


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