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Overconfidence in High Stakes Situations: Why Inferior Products Sometimes Win

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As a society, we place value in confidence. Confident people are consistently rewarded with higher pay, better relationships, and greater influence and control over their circumstances. They lead happier lives.

And this makes sense: Humans value certainty, so it follows that we’d prefer to associate with individuals who appear to be more certain of themselves and their beliefs because they appear to have more control over their lives and surroundings than those who don’t. Confident individuals seem to have greater insight into how the world is, and how events will turn out, and we’re attracted to that certainty.

One would think that as our world becomes more transparent, and knowledge about the world becomes more readily available, an individual’s confidence would become proportionally less valuable to others. In other words, as it becomes easier to independently determine the truth about what someone is confident about, (e.g. is San Francisco really the capital of California? Let me check Wikipedia. Are the Ravens really more likely to beat the 49ers? Let me check the Vegas line), using human confidence as a shortcut to determine what’s really going on should become less important.

What is peculiar, however, is that this is not true. Not at all. As a matter of fact, society continues to reward overconfidence. For the purpose of this post, I define overconfidence simply as “a level of confidence that is miscalibrated to the level of confidence appropriate to the circumstances” (for example, I am twice as good at Greg at ping pong, but I behave as if I were 10X better).

The idea behind why overconfidence is advantageous is that “it serves to increase ambition, morale, resolve, persistence or the credibility of bluffing, generating a self-fulfilling prophecy in which exaggerated confidence actually increases the probability of success.” 

In other words, overconfidence, on its own, can help the overconfident individual win. A self-reinforcing pattern emerges in these individuals’ minds, and overtime, they actually begin to use overconfidence as a tool.

If you have spent time with a star salesperson or athlete, you can likely attest to this phenomenon’s existence. The sheer energy those individuals emanate makes those around them feel secure. Teammates push themselves harder. Adversaries become riddled with doubt. As a buyer, you find yourself wanting to agree with them and associate with them -- even if you don’t have anything in common, find them to be slightly arrogant, or don’t even like them as a person.

While overconfidence can be an asset in business, it can also lead to problems -- especially with respect to decision making. Overconfident “experts” --not only salespeople, but Wall Street executives, doctors, and military leaders --  routinely make impaired decisions because they end up believing their own bullshit. And society suffers as a result: economic recessions, malpractice, military defeats -- have all happened as the result of overconfidence. 

Take for instance, the Battle of Gallipoli.The Battle of Gallipolli was the Turks' greatest victory of WWI. 

To set the stage, Britain at this time was at the height of its power. An unrivaled colonial superstar. Winston Churchill, then Britain’s First Lord of the Admiralty, had a brilliant idea to knock Turkey out of the war by launching a naval and land campaign to open up the Dardanelles straits, which was heavily defended on its western shore. From there, the Brits could have used Gallipoli as a base to attack Constantinople -- knocking Turkey out of the war. They could have also used that base to launch an attack on and on Germany and the Austro-Hungarian Empire’s less protected underbelly. If they had been successful, they could have ended the war 2-3 years earlier.

By just about any measure, the Turks were no match for British forces. While this campaign was not going to be a cakewalk for the Brits, they were a clear favorite by most accounts. They were not only a superior fighting force, they also initially outnumbered the Turks 10 to 1. 

The problem was, the Brits knew this.

Before the attack, Sir Ian Hamilton, the highly decorated Allied Commander leading the campaign, wrote in his diary 

“Let me bring my lads face to face with Turks in the open field, we must beat them every time because British volunteer soldiers are superior individuals to Anatolians, Syrians or Arabs and are animated with a superior ideal and an equal joy in battle.”

The Brits’ overconfidence prevented them from accurately reading the situation on the ground and adapting to it. While they outnumbered the Turks initially, this quickly changed as the Turks brought in reinforcements. Because of their initial advantage and misreading of the proportion of advantage, the Brits brought far fewer reinforcements than they needed. Fewer guns. Less water. And they took their sweet time doing it all. By some accounts, the British forces were barbecuing and sunbathing on the beach instead of preparing for battle for days on end. Even Sir Ian Hamilton was posted up on an island about an hour away from the action until news reached him that the battle was going awry. But by then it was too late. 

Map of Europe during WWI, arrow points to Gallipoli

Map of Europe during WWI, arrow points to Gallipoli

The Battle of Gallipoli turned out to be a disaster for the Allies. After eight months of fighting, no real progress, and an estimated 250,000 casualties, Britain decided to abandon the campaign. 

So what happened? Were Winston Churchill, and Sir Ian Hamilton incompetent in their management of this initaitive? 

No.

They were not incompetent. They were overconfident

Incompetence is certainty in the absence of expertise. Overconfidence is certainty in the presence of expertise.

And the Brits weren’t overconfident in Gallipoli because the battle was unimportant; they were overconfident because of how important the battle was. Because it was so high stakes, and because they were so good, they likely resorted to overconfidence as a mechanism to aid in battle. The problem is, the existence of overconfidence as an actual standalone tool does not exist. It is a phenomenon that humans relate to success in a sociological sense, giving it the power to affect change. But overconfidence cannot change the terrain in a battle. It cannot turn the weather in your favor. And most importantly, overconfidence is not enough to make up for lack of preparation and complacency. 

Overconfidence happens in highly competitive conditions, complex conditions, or conditions of real stress. It becomes a problem when people get older or more experienced, when they are doing things they feel very strongly about, or when things are very difficult.

Andy Grove knew this, writing in Only the Paranoid Survive, “Complacency often afflicts precisely those who have been the most successful.”

If you look at the “Closed Lost Reasons” in your CRM today, you will not find “Overconfidence” as an option. But if you were to think through the cause of the losses you or your team has suffered, overconfidence is likely at the root of some of them:

The prospect went with a competitor because you thought your product was so good you did not need to prepare as much as your competitor did for that key meeting. 

Your product was deemed “too expensive” because you failed to properly explain the value of your product, as you thought that value was evident. 

You didn’t think it was imperative to develop a relationship with the new CFO because the results of the value assessment should be enough.

The fine line we must walk as sales professionals is one where we embrace confidence, even overconfidence. We must not only display overconfidence: we must actually be overconfident. But we must not allow overconfidence to make mistakes of preparation or underestimation. 

Show up prepared. Multithread the deal. Get a second opinion on everything. And most importantly, never underestimate the competition.