Underdogs & The Art of Battling Modern Day Goliaths

Strategy Matters

[su_dropcap style=”flat”]E[/su_dropcap]VERYONE loves an underdog. We grew up learning to cheer on the underdog because we see ourselves in them. Yet the power of the underdog is a phenomenon not easily understood. How do underdogs overcome great difficulties, persevere, and defeat stronger opponents? Is this just a fluke or is there some kind of strategy or set of conditions that need to occur? Think back to biblical times when a young shepherd boy named David took on Goliath the giant Philistine warrior. David would have had better odds in winning the lottery than defeating Goliath, who stood close to seven feet tall. Yet, as history records it, David’s spiritual faith and skill in using a simple sling to hurl a small rock to Goliath’s exposed forehead proved to be the decisive factor. This article examines the power of the underdog, to understand where power and advantage really lie. It looks at the modern-day “shepherd and giant” through stories of what it took for the former to outfox, outperform, and outlast the latter.

Being an underdog means that the individual or group is expected to lose in a contest. This could be a sports team, country, or individual up against a formidable force. In sports, history records how “the Dream Team” of professional basketball players from the United States — the best of the best — fell victim to a team of unknown players from the island nation of Puerto Rico in the 2004 World Olympics. In country conflicts, history shows that a band of nomads under the command of T.E. Lawrence (“Lawrence of Arabia”) defeated a heavily fortified and modern Ottoman army at the Battle of Aqaba. With individuals, the likes of Nelson Mandela, Gandhi, & Martin Luther King come to mind in how the disenfranchised took on strong adversaries through non-violent tactics. In explaining what it means to be an underdog, Malcolm Gladwell says:

“The fact of being an underdog changes people in ways that we often fail to appreciate. It opens doors and creates opportunities and enlightens and permits things that might otherwise have seemed unthinkable” — Malcolm Gladwell

The master storyteller and author Malcolm Gladwell offers insight into how underdogs prevail over stronger adversaries in his book “David and Goliath: Underdogs, Misfits, and the Art of Battling Giants” (2013). He challenges how we think about obstacles and disadvantages, while drawing upon history, psychology, and compelling examples to portray a contemporary David. While not a scientific study, Gladwell uses real-life stories to make the reader think differently about being an underdog and what it takes to overcome odds. Clearly not all underdogs win, but there are certain tactics that help compensate for inherent weaknesses to improve the probability of success.

As Gladwell does so well, he shares the following stories as evidence to what an underdog is capable of doing:

  • How the famed physician Jay Freireich overcame the loss of a father early in life and endured family hardship to help children fight cancer.
  • When the civil rights leader Fred Shuttlesworth overcame the fear of white hate groups through courage and tenacity to fight on.
  • How Goldman Sachs President Brian Glazer overcame learning disabilities to achieve success in leading a global investment firm.

In particular with Fred Shuttlesworth and others engaged in social struggles, Gladwell addresses the “Principle of Legitimacy.” He uses the conflict in Northern Ireland over religiou

s differences, social unrest in the United States over perceived authority issues, and the civil rights protests in the Deep South over racial inequality to describe how underdogs function. In each of these cases, legitimacy in the authority figure needs to be met in order for the underdog to acquiesce. Gladwell builds on these stories to elaborate on how legitimacy issues can rally underdogs to challenge modern-day giants.

• Northern Ireland in the late 1960s witnessed how the Catholic minority became disobedient in response to how British “peacekeepers” were allegedly mishandling their authority with prejudice.

• The area of Brownsville within Brooklyn NY in 2003 experienced similar legitimacy issues with the local police in how authority was being exercised.

• Birmingham Alabama in 1963 experienced how Bull Connor and the local Ku Klux Klan misused its power to counter nonviolent protest over civil rights, as covered throughout the world in vivid photographs.

Just as the local Alabama police exercised its authority over civil rights protests in the 1960s, the use of excessive force proved illegitimate to many and made matters worse. This type of scenario can strengthen the underdog’s will to fight. The ongoing crisis in Ferguson Missouri and what happened last year in Baltimore over Freddie Gray’s questionable death comes to mind. Gladwell’s point is that legitimacy needs to exist with the authoritarian figure in order for social obedience to occur. For instance, it was only through the actions of a new leader that the police’s image of illegitimacy with the Brownsville community got turned round. Rather than use more force to respond to civil disobedience, the police opted to address the core problem of mistrust by building bridges into the community to ease tensions and restore legitimacy.

Using unconventional tactics to battle today’s Goliath is not a guarantee for victory, but it can help. Gladwell cites a study that examined the outcomes of international wars over the past 200 years between small and large countries. The results support the claim that when the smaller country uses unconventional tactics to fight, its win probability increases to just over 60 percent. Recent history shows how guerilla-like tactics were used in Vietnam to protract the conflict where the weaker side outlasted a stronger adversary. In contrast, the Tet offensive (1968) proved disastrous for the underdog when it decided to directly challenge the “giant” through conventional warfare. A similar outcome would have certainly occurred if David took Goliath on in hand-to-hand combat. Fighting the giant in his style of battle puts the underdog at a disadvantage.

Being an underdog can also involve physical and mental handicaps when faced with social and career challenges. Consider those who suffer from the learning disorder dyslexia, for instance. Being dyslexic imposes difficulties in being able to hear and manipulate sounds. Many of those inflicted with this condition learn to develop other skills as work-around methods, to cope with limitations in ways that can yield positive results. Gladwell lists several famous underdogs that overcame dyslexia to give hope and inspiration to others with similar handicaps. This includes: Richard Branson, Ted Turner, and Steven Spielberg. In dealing with such handicaps as dyslexia, blindness, and autism, an underdog has various options available from which to decide what to do and how to compensate.

Gladwell uses the story of David Boises, one of the most successful trial lawyers in the United States, to describe these options when faced with a serious learning disorder. Recall what the shepherd boy David did to refine his sling skills to compensate for being physically small. Similarly, Boises exploited other skills out of necessity to cope with dyslexia, such as memorization recall and comprehension. He used these highly developed skills to get through law school and become an expert litigator. Gladwell describes how “compensation learning” is used to fill a void when a capability or skill does not exist, where one is weak in a particular area and aims to fix it. In the case of David Boises, he relied on his core strengths to work around not being able to easily read legal documents due to dyslexia.

Whereas this is an amazing story of how Boises overcame a serious learning disorder, no one wishes dyslexia on themselves, their children, or others. The takeaway is how this type of underdog, despite handicaps, has the potential to overcome significant challenges. Clearly not all who suffer from physical and mental issues triumph like those cited in Gladwell’s book. David Boises and several role models like him “succeeded, in part, because of their disorder — they had learned something in their struggle that proved to be an enormous advantage,” according to Gladwell. Boises the underdog would not have become the same successful trial litigator had he not developed unique skills through compensation learning to overcome major impediments.

In business, innovative startup companies can take on the persona of a modern-day David when challenging industry giants. This can be said for when Airbnb first broke into the lodging industry in 2008. Using social media as a “sling” to hurl disruptive forces, Airbnb employed unconventional methods as part of its business model to survive and ultimately thrive. In dealing with giants, smart business strategy often involves creative ideas, product differentiation, and the use of new technologies to achieve competitive advantage. This is exactly what Airbnb did to challenge the major hotel chains. As the underdog, Airbnb engaged in a series of competitive moves that were difficult for the giants to respond to quickly, much less catching them unaware and flat-footed. Rather than go head-to-head with its adversaries, Airbnb opted to fight an unconventional campaign, using new social media technology to connect with a younger set of customers looking for a different type of lodging experience. As for weapon strength, Airbnb wielded greater flexibility and geographic coverage than what the major hotels could easily provide customers. Having since become a giant in its own right, Airbnb now has over 1.5 million listings in 34,000 cities and 190 countries available for customers to secure lodging.

Many small, innovative firms rely on creativity, invention, and speed to market as their “slings of choice” when taking on industry giants. Similar to what Boises did to battle dyslexia, the underdog needs to compensate for certain weaknesses by leveraging its inherent strengths through different, less conventional tactics. This ability factors into what separates the victors from the losers, what propels an underdog with known deficiencies to persevere, to double down on motivation and resourcefulness in order to survive.

In recalling how Lawrence of Arabia led the underdog camel-backed nomads to victory over the mighty Ottomans, his strategy was about using speed and time — not hitting power — to compensate for other weaknesses. Like Lawrence and many other individuals cited in Gladwell’s book, one needs to understand what to exploit, where the larger opponent is vulnerable to defeat, and how to wield effective force. Lawrence had speed and time, David Boises had a good memory, and David the shepherd boy had his lethal sling.

With all that is cited in Gladwell’s book, in business and in personal life, one begins to understand what it takes to be a stronger underdog, to take on the giants and deal more effectively with life’s many challenges. The stories and lessons learned challenge us to think differently, to realize the type of strategy needed to defeat the modern day Goliath. These key take-away lessons can be summarized three ways:

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  • Never play into the giant’s strengths. Instead, use unconventional means to leverage the underdog’s strength while exploiting the giant’s weakness. One needs to balance the odds through unconventional tactics, to employ smart strategy to outfox, outperform, and outlast the giant. Whereas Goliath was an expert in various types of warfare, he was completely caught off guard by a simple sling. From a 21st century perspective, think how disruptive underdogs can take on industry giants through unconventional means, e.g., innovation, rapid change, and new technologies.
  • Learn to adjust and deal with weaknesses. The concept of Compensation Learning applies to virtually everyone. Each of us is different with varying levels of ability. How weaknesses are recognized and dealt with can directly influence the ability to prevail over the giant, as David Boises did in learning how to compensate for his dyslexia through other, highly developed skills.
  • Pick your battles carefully. Giants who function without legitimacy are vulnerable to defeat over time. In response, underdogs need to chip away at the giant’s perceived strengths to gain a foothold, and ultimately push on to victory while exercising the two bullets above on strategy.[/message][su_spacer]

Perhaps one of the most visible upsets in contemporary sports occurred in ice hockey at the 1980 World Olympics. The underdog U.S. amateur team went up against the odds-on favorite from the Soviet Union. Though not quite as much of a mismatch as when David challenged Goliath, virtually everyone assumed that the giant bear from Russia would earn another consecutive Olympic gold medal. In taking on the modern day Goliath, U.S. hockey coach Herb Brooks placed the following message onto his “troops” as a rally cry for victory:

This is your time! Now go out there and take it![su_spacer]

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