Underdog Leadership

The necessity of stacking the odds against you and your organization

Thoughts on Excellence Free E-Newsletter Series
Volume 12, Issue No. 10
January, 2014

By Dan Coughlin



When I was growing up my dad had a variety of sayings that he repeated many times. His favorite was, “I always cheer for the underdog.” If two teams were competing and he didn’t know either one, he would ask, “Who’s the favorite?” After I told him, he would say, “Okay, I’m cheering for the other team.” I suppose since he was born six months before The Great Depression that throughout his childhood and teenage years he felt very much the challenge of having little or no money to achieve what he wanted in life. Consequently, he was always trying hard at whatever he did and cheering for the person or group who seemed to have less going for them.

And that was part of his key to success.


The St. Louis Cardinals have won 11 World Series, which is the second most in the history of Major League Baseball. Most teams would be thrilled to win five or three or even one. Yet somehow the Cardinals always position themselves as being underdogs against all those great big successful teams that they feel honored to just play against. I live in St. Louis, and every year the season starts off with, “We are going to have to work incredibly hard every game just to have the opportunity to have any success at all.” The Cardinals’ fans start hyperventilating on the first pitch of the first game and they don’t stop focusing until the last pitch of the last game.

And that is part of their key to success.


Successful underdogs don’t focus on what they don’t have. They also don’t give in to the temptation to say they don’t have a chance against overwhelming odds. Instead they look for a tiny bit of leverage they can turn to their advantage. Of course, Apple couldn’t beat out IBM in the 1970s, until they did. Of course, IBM the fallen king of hardware could never become a dominant global services company, until they did. Of course, Wal-Mart couldn’t replace the successful retailers of the 1960s so they just kept trying harder and harder at adding value to the people who were attracted to them. Of course, Bill Marriott couldn’t take his company from root beer stands to a successful hotel business, until he did. Successful underdogs focus on their current reality and they leverage what they can leverage to improve a little bit at a time.

And that is part of their key to success.


Individuals and organizations who hang on to the underdog mindset keep on keeping on. They never feel like they’ve arrived or completed their journey. They just keep on digging and working and searching for ways to get better and add more appropriate value to their customers.

And that is part of their key to success.


If you’re running a startup business, you’re an underdog. And that’s good. If you’re running an organization that is number one in the world or in your marketplace, then you need to make sure that you retain or regain the attitude of the underdog. Over the past 16 years I’ve had the opportunity to work with executives at a variety of companies who were number one in the world at the time I worked with them. These included Marriott (hotel lodging), Anheuser-Busch InBev (beer), Coca-Cola (beverages), McDonald’s (quick-service restaurants), and Toyota (automobiles). In every meeting I attended and in every conversation I had with these executives I never once heard anyone say, “We’re dominating the market and I doubt anyone can catch us so we’re just going to take it easy this year.” Instead I heard them say things like, “We have to focus even better this year in order to be successful. We have to work smarter and pay attention better to our customers. The odds are against us so we have to build even better teamwork and create better value for our customers if we want to keep on being successful.”

And that is part of their key to success.


Create a realistic competitive challenge. It doesn’t matter where your organization is relative to your competition. Whether you are at the top or the bottom of the heap, you need to craft a realistic competitive challenge. And then you need to step back and think about how to succeed in the face of that challenge.

An unrealistic competitive challenge means that it is extremely unlikely you will come anywhere near hitting the mark you’ve set for your organization. At the end of the year people aren’t inspired. They’re demoralized. It feels like the boss has lost all touch with reality. A startup company is not realistically going to dominate the world in pizza sales within 12 months. I know, I know, you’re going to tell me about some example of where that happened in some industry. The once in a blue moon examples are intriguing, but not very helpful.

On the other hand, aiming for a big goal can still be a realistic competitive challenge. When John Kennedy said the United States would put a man on the moon by the end of the decade, it seemed impossible at first glance, but was it really? He made that statement on May 25, 1961, which was a month after the Russians had sent their own cosmonaut into space. That meant the U.S. had eight and a half years to send one of their own astronauts to the moon. A difficult competitive challenge, yes. Unrealistic, no.

What realistic competitive challenge can you create for yourself and/or your organization that will cause you to be in the underdog role, where the odds are stacked against you achieving it?

If you’re number one, then maybe the goal is to be number one more times in a row than anyone else has ever done it. Or maybe you can redefine the industry you’re in to expand your competition. Or maybe you can set a challenge to do something that no other organization has ever done before. Remember Apple’s original goal to make a personal computer that would sit on everyone’s desk. If they could get one on one person’s desk, then they could get one on everyone’s desk.

Be the underdog. Stack the odds against yourself. And then work smarter and be cleverer at understanding your current reality than you’ve ever been before. Leverage what you can leverage in order to make progress. Cheer your team on to beat the odds that are stacked against them.

And that will be part of your key to success.


Admittedly I am a huge fan of Malcolm Gladwell. I’ve loved all of his books, but I really think his best effort is his book, David versus Goliath. That book inspired this article. He does a masterful job of explaining why disadvantages are so important to have and why powerful people are not always as powerful as they first appear. I really encourage you to read it and think about how you can apply the ideas in your life and in your work.

Republishing Articles

My newsletters, Thoughts on Excellence, have been republished in approximately 40 trade magazines, on-line publications, and internal publications for businesses, universities, and not-for-profit organizations over the past 20+ years. If you would like to republish all or part of my monthly articles, please send me an e-mail at dan@thecoughlincompany.com with the name of the article you want in the subject heading. I will send you the article in a word document.

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