Luck and Leadership

What factors play a role in leaders that are lucky?

I wrote an article a while ago about the Fallacy of Self-Made. In that article, I argue that many of the most successful people, whether in business or any other endeavor, have a large amount of luck to thank for their success. By luck, I was referring to timing, location, other people, etc. My main point was that often successful people mistakenly think it was solely their skills or hard work that made them successful and therefore others should blindly follow everything they say or do. We’ve seen plenty of these pontificators lately and with social media, I suspect we’ll see plenty more. 

In this article, I want to explore the idea of luck a bit more and specifically with regards to leadership and the intersection of these two phenomenons. Are great leaders luckier than others? Do they make their own luck? Many great leaders have weighed in on luck and usually their words focus on how preparation can help someone become luckier. For example, Green Bay Packers football coach Vince Lombardi said, “Luck doesn’t favor the lucky; it favors the prepared.” Thomas Jefferson, the 3rd U.S. President, supposedly said, “I’m a great believer in luck, and I find the harder I work, the more luck I have.” although there is no attributable source. Even the Stoic philosopher of Ancient Rome, Seneca wrote, “Luck is what happens when preparation meets opportunity.”

However, we all know of many examples where despite plenty of preparation, luck was not present. In the late 1950s a band called The Quarrymen were playing an opening night gig at a Liverpool cafe called the Casbah Coffee Club that was owned by Mona Best. The band needed a drummer so they asked the owner’s son, Pete, to sit in. This led to a series of gigs in Hamburg, Germany where Pete drummed and the band found their trademark blues-infused sound. They also began to amass crowds of giddy fans. Despite Pete feeling like he became close to the other young men in the band, when they returned to London, he was sacked. The band became The Beatles and the drummer they replaced Pete Best with was Ringo Star. Now, before you think that Ringo was probably a better drummer than Pete and therefore preparation was the key luck factor, John Lennon famously quipped, “Ringo wasn’t the best drummer in the world… Let’s face it, he wasn’t even the best drummer in The Beatles.” There have been a lot of theories on why Pete was replaced by Ringo but it’s likely that John, George, and Paul just bonded better with Ringo, who they met in Hamburg when he was performing with Rory Storm and The Hurricanes. 

So, if luck doesn’t always favor the prepared, what other factors might be involved? In a 2008 Military Review article, Major David Cummings of the Jamaica Defence Force, developed an equation for luck. He based this on his study of military leaders in history and published works, such as FM 6-22 the U.S. Army's field manual for leadership. His proposal is that there are four factors that play into creating luck – preparation, control, confidence, and opportunity. 

Luck = ∑(preparation + control + confidence + opportunity)

Major Cummings states, “Luck, then, appears to be influenced by a combination of confidence (desire, belief, and experience), control, preparation, and opportunity. Therefore, my definition of luck is successful or unsuccessful outcomes that appear to result from the convergence of confidence, control, preparation, and opportunity…Where and when these factors converge is usually where and when ‘good luck’ occurs.” Developing this concept further, he postulates that luck is a curve where preparation, control, confidence, and opportunities all combine to deliver better luck…to a point. Beyond some point, these factors can actually decrease ‘good luck’ and instead drive an increase in ‘bad luck’. What Major Cummings is implying is that with each of these factors, too much is not a good thing. When there is too much preparation there might be a failure to execute, which can obviously be a real problem. Too much control can lead to micromanagement. Overconfidence can lead to leaders and teams being sloppy in execution. Too many opportunities can lead to a diffused impact or confusion over which one to seize. Let’s take a look at these from a product and engineering perspective.

Preparation

In modern product development we have both a discovery and delivery cycle that are nearly constantly in process. One can think of the discovery as preparation for delivery. If our teams get infatuated with discovery and only focus on that phase, we will slow down or even stop the delivery phase. Too much preparation in terms of research or hypothesis creation can actually be detrimental. 

Control

While control is usually a good thing, over control of our product development processes can lead to micromanagement which is exactly the opposite thing we want with empowered teams. In modern product development our teams should be empowered to make their own decisions about what features they are going to try to achieve a particular customer or business impact. For example, if the team is tasked with a goal of improving conversions from the search page, they should be encouraged to develop hypotheses based on the available data about what changes might best achieve their goal. While the product and engineering directors and VPs should pay attention to what the teams are working on, if they get too involved and begin dictating product ideas, they are starting to micromanage which stifles innovation and takes away empowerment from the teams. 

Confidence

How many companies have we seen taken down by smaller, more nimble competitors because of overconfidence in their market position? Just because you’re on top, doesn’t mean you are destined to stay there. In fact, the higher you are in your particular market or industry, only means you have that much larger target on your back. As Andy Grove, the third CEO of Intel Corporation, said, “Success breeds complacency. Complacency breeds failure. Only the paranoid survive.”

Opportunity

In any interesting industry or business, there are always more opportunities than you can go after. The power of focus is worthy of an article or two in its own right but for now suffice it to say that spreading your resources out in order to tackle too many opportunities will only guarantee that you don’t succeed on any of them. Warren Buffet said, “The difference between successful people and really successful people is that really successful people say no to almost everything.” And, Steve Jobs said “People think focus means saying yes to the thing you’ve got to focus on.But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully. I’m actually as proud of the things we haven’t done as the things I have done. Innovation is saying no to 1,000 things.” Saying ‘no’ is hard but that’s what leaders do. 

The exploration of luck in leadership uncovers a complex interplay of factors that extend beyond mere preparation. Major Cummings' equation of Luck = ∑(preparation + control + confidence + opportunity) highlights the multifaceted nature of luck, emphasizing that it's not solely a product of being prepared, but also a result of how well one manages control, exudes confidence, and seizes opportunities. However, as we've seen through various examples, an excess in any of these elements can lead to diminishing returns or even adverse outcomes. The parallels drawn from product and engineering perspectives further illustrate this delicate balance, demonstrating how overemphasis on one aspect can hinder progress, innovation, and success. Leaders, therefore, must strike a fine balance, not just in preparing and controlling, but also in maintaining confidence, discerning opportunities, and most importantly, knowing when to say 'no.' This equilibrium is what often differentiates those who experience 'good luck' from those who don't. Ultimately, while luck plays a role in leadership and success, it's the leader's ability to navigate and balance these critical factors that often determines the extent of their fortune.