Why Being A Leader Is Harder Than It Looks

Darren Ryan
The Startup
Published in
4 min readDec 3, 2019
Photo by Alfred Aloushy on Unsplash

Lots of people aspire to be leaders. There are plenty who don’t.

For those who are not leaders, it can seem like an easy job. For the leaders, it can often feel like a lonely and thankless existence.

Leadership doesn’t come with a step by step manual. Much of it is based on experience and learning through personal trials and errors. Sure, there are plenty of courses and books on leadership, but they usually only teach the general principles.

The truth is, leadership is personal. Not only to the individual, but also to the environment it takes place in. That’s why, to be a great leader, you need to observe great leaders first. You need to study them in their environments, understand how they operate, learn how they make decisions and take note of how they react to events.

Leaders are no longer the charismatic extroverts who were once the only type of people deemed capable of motivating teams and building successful businesses. Today’s leaders are arguably far more complex than they’ve ever been as they face rapidly changing business landscapes that require innovation, new ideas and more of an understanding of people than ever before. They certainly don’t need to be extroverts. In fact, they don’t need to classed in any way at all. Today, great leaders come from all walks of life and an array of backgrounds.

I’ve been privileged enough to work under some fantastic leaders. I’ve also studied many leaders (both past and present) in the pursuit of understanding what leadership is. I’ve managed teams and led organizations to success, but what I’ve found along the way, is just how difficult the job is.

Here are a few reasons why.

Leaders have responsibility

This may seem obvious at first, but it’s a pretty big deal. When you’re not in a leadership position, you don’t usually need to manage or control many of the organization’s resources. This reduces the amount of risk you’re exposed to. You’re not usually held accountable or responsible for the mistakes or failings of others, which makes it a ‘safer’ place to work.

A CEO, for example, can be responsible for hundreds of people and their families (depending on the size of the company). The CEO’s decisions on how he/she runs the company can have a significant impact on those people. The responsibility is enormous.

Leaders are exposed to risk all the time, and they need to be consistently responsible for managing that risk.

Leaders need to do the opposite of everyone else

While communicating with people is not that difficult, it can be challenging to connect with the people you’re leading.

When there is panic in the room, leaders need to keep calm and diffuse the situation. When the team is demotivated and tired, the leader needs to keep them energized to push on. Even when a team is ecstatic about a particular success, they need to keep them grounded.

It’s a tough position to be in. As humans, one of the most powerful forces we’re exposed to is our emotions. They can be difficult to control. But leaders have a duty to themselves and to their teams to keep them in check. If they don’t, they risk losing the respect of those around them, which in turn can result in failures.

Leaders need to be adaptable

Leaders need to be able to adapt to any situation almost immediately. They rarely have the privilege of focusing on one piece of work at a time or dealing with one problem at a time. They could be talking about resourcing one minute and then marketing the next.

Being able to adapt while remaining focused is an essential skill for a leader, but it can be difficult and tiring.

It’s lonely

When I was promoted to my first management role, I realized quite early on how isolated I was. Although my superiors were supportive, they expected results. On the opposite side, my team had their demands. It was tough learning to juggle the needs of both these stakeholders while also ensuring my development needs were met.

The higher up the ladder you go, the more lonely it gets. Senior leaders, directors and CEOs can find their roles extremely isolating as more people depend on them while they get less and less support. Expectations are high at these levels, and the margin for error narrow.

Decision making

This gets harder as your responsibilities grow. As a leader, you often have the last say in the decision-making process. Signing on the dotted line can be daunting, especially when you are responsible for the whole process in the first place.

Depending on the role, leaders have to sometimes make difficult decisions. Some of these decisions may even hurt others.

There is a great scene in the TV mini-series, Band of Brothers where Donny Wahlberg’s character (Sergeant Lipton) is talking about one of the leaders of Easy company, Luitenant Norman Dike: “ Dike wasn’t a bad leader because he made bad decisions, he was a bad leader because he made no decisions”.

Decision making is a skill that takes time to develop. It comes with experience, but can be one of the most difficult to master.

Leadership means giving of yourself. It means putting yourself last. It means dropping the ego so the team can thrive. That’s what makes it difficult. But get it right, and your organization stands a better chance of overcoming adversity and achieving success.

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Darren Ryan
The Startup

Leader, writer, entrepreneur. History fanatic. Ocean lover.