Leadership: Easy to Say, Simple to Define, Almost Impossible to Pin Down

Leadership. According to Merriam-Webster’s dictionary, this means the office or position of a leader, a capacity to lead, the act or an instance of leading.

Gee, thanks. That really helps, doesn’t it? Okay, so let’s try ‘lead.’

To lead. To guide on a way especially by going in advance, to direct on a course or in a direction, to serve as a channel for.

Okay, not a whole lot better, but it’s getting us there, right? I really like the first definition for lead: “to guide on a way, especially by going in advance.”

As an entrepreneur, you are, almost by definition, a leader. You are going ahead of the people who will eventually be following you and, hopefully, assisting and supporting you in this venture.

Leadership, then, is the act of going in advance, showing others how it’s done, and helping people find and stay on a specific course.

Story Time!

I want to tell you a quick story. You might have heard this before, or maybe I mentioned it in a previous blog or podcast, and that’s okay. It’s simple and to the point.

A couple wanted to sail across the Pacific Ocean. They were planning on leaving from San Diego. Their destination: Japan. More specifically, Tokyo.

They weren’t the most seasoned sailors, but they had been practicing for many years. Nothing like this, though. So, knowing how important it would be to have an experienced captain guide them, they hired somebody to lead the way.

They didn’t want this captain to pilot their ship, though. They wanted to follow behind another boat. The captain agreed. As long as communication was strong, he didn’t foresee any issues in leading them across the ocean to their destination.

What this couple failed to realize, however, was that their captain, even though he was fully licensed and had been sailing for most of his adult life, had never crossed the ocean before. The farthest he had ever gone was from San Diego to Los Angeles. Maybe Catalina Island, too. That was it.

So, unbeknownst to them, this couple was following their captain, maintaining at least  thousand yards’ distance between their boat and his. They met some choppy seas and some incredibly calm, blue waters along their journey.

They saw some whales, dolphins, and the occasional shark fin break the surface. It was simultaneously thrilling and terrifying. For the couple, it was an absolutely wonderful trip. Once in a lifetime.

After several weeks, they finally spotted land in the distance. Exciting. They approached and kept following their captain. By the time they reached shore, things weren’t adding up. This was no bustling city. Nothing like the Tokyo they imagined.

‘Maybe he brought us to a town on the outskirts,’ they thought.

No, that’s not what happened. Their captain, because he wasn’t a true leader, because he wasn’t honest and didn’t ask for any advice or counsel, ended up drifting by one simple degree. Instead of sailing right into the heart of Japan, they cruised through the East China Sea, up through the Yellow Sea, and landed on the coast of North Korea.

Before long, armed North Korean soldiers came out to meet them. They were arrested on the spot.

Now, this story is complete fiction, but my intention is to highlight a very important point about leadership. You can define it, understand the basics of it, but a true leader is one who is not just going to show the way, but is going to make sure he or she helps those following to reach their destination.

How can you ensure that?

By understanding the responsibility you carry as a leader. By honing your skills and admitting you can’t do everything on your own. By accepting you don’t possibly know everything you will need to know to successfully run a business.

People define leadership in many different ways. Just because you have a dictionary to give you some basic counsel doesn’t mean you’re going to achieve consensus. In fact, reaching consensus about what leadership is, the best type of leadership, the right ‘style’ or how to develop those skills is almost impossible.

Most people tend to define leadership as a process. In other words, it basically talks about a person’s skills, actions, or decisions. We hear terms like ‘leadership style’ and assume that it characterizes certain traits.

Essentially, all of this talk about leadership is very similar to mythology. We elevate the men and women who exhibited exceptional leadership skills in the past and achieved enviable results. They become idols.

However, that doesn’t mean we can simply study the actions and decisions of an exceptional leader and emulate it and expect the same results. (Honestly, how often does that actually happen?)

A great leader is not always (or even mostly) about a person who does the right thing at the right time. It’s about the entire system, the organization, the relationships that connect people to those leaders and how they support one another.

Yes, there are certain people who have incredible skills as leaders and can essentially achieve desired results time after time after time in one environment after another.

But don’t fall into the trap of assuming that people who are venerated as some of the best leaders in history always got it right.

George Washington is often venerated as one of the best leaders in history, yet he was a miserable failure most of the time. He was a mediocre colonel who took on the unenviable task of trying to drive the British out of Boston.

The only way he could foresee achieving this goal was to take Bunker Hill, and the only way to take Bunker Hill was by doing the impossible in one night. He managed to motivate his men to move enough cannons into place and dig the proper trenches, all in one night, which everyone, including the British, assumed was impossible.

So, when the British looked up the next morning toward Bunker Hill and saw Washington and his soldiers peering down on them with cannons ready to fire, they knew they had lost. Strategically, they understood retreat was the only reasonable decision.

But let us not forget that after this victory, Washington led his men to one defeat after another, losing Manhattan then Yorktown and being chased down through New Jersey in the middle of winter, with many of his soldiers unpaid and shoeless, trudging through the snow and ice with bare, frostbitten feet.

Abraham Lincoln is another great example. His entire life before he became President of the United States was one series of failures after another. Lost elections, failed businesses, having to pay back a massive debt to a friend after a failed business venture (and it took him well more than a decade to pay all that debt back).

He lost almost every single election he ran in, from local to state to national levels. Yet, he is remembered as one of the greatest leaders of the United States because of his actions during the Civil War.

Be Willing to Lead, Not Rule

Perhaps one of the best pieces of advice anyone could offer when it comes to discussing leadership, leadership skills, leadership styles and so on is to just say, “Be willing to lead, not rule.”

When you run a business, it’s your baby, your prized possession. It’s something that you put more time and energy into than almost anything else in your life.

It’s a source of pride. It’s a financial investment. It represents perhaps life savings, hundreds or even thousands or tens of thousands of hours of your time and effort.

It might represent sacrifice, giving up time with your family, missing your kids playing in sporting events, their school play, or even being there when they were born.

There is so much that entrepreneurs give up as they pursue their goals of being business leaders. As a result, there is a sense of ownership to that business. After all, you do own it (so long as you don’t have a team of partners).

Let’s assume that you own this business yourself (or maybe with one other person). It is still yours. You want things done the way you want them done.

Suddenly, you can start drifting. It might not seem like a lot when you’re in the middle of the ocean, but one small degree can move you from landing at your destination to being in the worst place you could possibly be in the world.

Abraham Lincoln had to make some incredibly difficult choices during his presidency. One of the toughest was when Fort Sumter was surrounded by Confederate soldiers in 1861. They had effectively cut off food and other supplies to the Union soldiers at the fort.

Yet, Lincoln understood he could not fire the first shot, not if he wanted to get the rest of the Union behind this effort against the Confederate South. When the Confederates opened fire, Lincoln had the support he needed to go into this war and press on to victory.

That is a leader. Knowing that there were men begging for help, but that he decided whatever sacrifice was made there was for the betterment of the nation long-term.

Washington had to make difficult choices, too. At one point, farmers who had joined the revolution with a promise of money they could send home (because they weren’t there to farm the land) were becoming frustrated without any payment for almost 2 years.

Two of Washington’s soldiers made the decision to leave, but they were caught before they got too far. He knew these men on some personal level, and had to decide their fate. He had them executed, not because he wanted to, but because he understood if he let them go, then others would soon follow and the war effort would be lost.

It’s not pretty, but leaders do have to make difficult choices. There will be times when you’re faced with struggle and strife among your team because one of your most talented or intelligent workers is abrasive to others. Sometimes you have to cut the best players to build the team up.

Keep in mind that it’s not you that defines the totality of quality leadership, but the entire system.

Those two men under Washington’s command were simply worried about their wives and children back home who weren’t getting the (promised) money they needed to survive. According to Washington’s own hand in his diary, they were good men, good friends. It wasn’t a decision he came to lightly and was one that haunted him the rest of his life.

Yet, the system, the revolution in this case, the birth of a nation was Washington’s primary focus.

Having strong leadership skills doesn’t really depend on the style you choose, but your understanding that it’s about the system. It’s about the business you’re building, which includes its success, but also the team you surround yourself with.

You can read countless articles on leadership, but it really comes down to one simple thing: is this business really all about you or about something just a bit bigger than you? When you can answer that question honestly, you will determine who you really are as a leader.

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