The 4 Best Leadership Books To Read in Your 20s

Your twenties are an important time in your life. Some people even argue it’s the defining decade of your life.

If there’s one quality you should master as a young adult, it’s leadership. And one of the best ways to learn how to be a leader is reading books.

In this post I’ll share my top four books—the best leadership books, if you ask me—to read in your twenties. 

Why these particular books?

They’ll help you as you rise in your career. They’ll help you if you decide to go into business for yourself. They’ll help you navigate all the different roles of leadership you might take on in your life—from manager to CEO to parent to community leader and more.

One of these leadership books is nearly 100 years old.

Another has lessons from life-and-death situations.

There are different leadership roles, styles, and circumstances covered in each of the books, but they all share this common thread: You’ll become a much better leader after reading and implementing the strategies they teach.

 

“How To Win Friends and Influence People” by Dale Carnegie

This book is the best leadership book on this list because the principles are timeless.

Dale Carnegie was born in 1888 and his principles are just as relevant now as they were back then because (spoiler) people haven’t changed. Even though technology and modern life have evolved, human nature remains the same.

“How to Win Friends and Influence People” has one core philosophy that runs through the entire book:

Everyone’s favorite person in the world is themselves.

It’s a book about having empathy for others, meeting people where they’re at, and influencing them by making a real effort to know and understand them. This leads to the first core concept of the book:

 

Take a genuine interest in other people

When it comes to your friends, your community, or the teams you’re leading as a manager or boss, showing actual concern for the feelings and perspectives of others is one of the easiest ways to influence people because, above all else, people want to feel understood.

 

Practice praise and honest appreciation

Of course, you can still help others correct their mistakes and encourage their growth. But this means providing constructive feedback in private and praise in public. If you’re going to “criticize,” do it one-on-one, sharing strategies and practices for improvement instead of criticizing people for who they are. 

Also, don’t provide faint praise. Praise people when they do things worthy of praise. Instead of constant (emptier) praise, recognize others when appropriate. It will mean more because it’s sincere.

 

Be a good listener

If you want people to feel like you’re a great conversationalist, spend more time listening than talking. People love to talk about themselves. Being fully engaged and not distracted, mirroring back what they say, and showing them you know where they’re coming from is the way.

This is true in sales, management, or influencing people in general. There’s a concept called “pacing and leading,” that is considered a form of conversational hypnosis because it involves mirroring the person you’re talking to and understanding them deeply. Those two combined are quite persuasive.

 

 

“Wooden on Leadership” by John Wooden

John Wooden is one of the most successful basketball coaches of all time.

His UCLA Bruins won 10 NCAA National Championships. They also had an 88-game winning streak that lasted from 1971 to 1974. This remains the longest winning streak in NCAA Division I basketball history.

He wrote a book about the principles he used to help his teams win, and it’s one of the best leadership books because it has principles that can teach you how to lead at any time.

 

The Pyramid of Success

John Wooden created a framework for building blocks of personal and professional excellence. It’s a pyramid with 15 traits.

The foundational qualities:

• Industriousness
• Friendship
• Loyalty
• Cooperation
• Enthusiasm

The middle layers:

• Self-control
• Alertness
• Initiative
• Intentness

Near the top:

• Condition
• Skill
• Team spirit

The crown jewel:

• Competitive greatness

Surrounding the pyramid are 12 additional traits, including integrity, reliability, and adaptability.

You don’t have to copy John’s exact frameworks, but having frameworks will help you guide your team. If everyone on your team has a set of principles to follow, then you don’t have to constantly tell them what to do. The principles guide behavior. All someone on your team has to do is measure themselves by the principle, and they’ll know what to do. 

 

Focus on the process, not the results

Wooden wasn’t concerned with the results of the game. He did not care whether or not the team won or lost. He cared that the team did everything possible to prepare and gave 100% effort in both practice and games. His practices were meticulous.

Every minute of practice was accounted for. He iterated the practice schedule constantly. He even went so far as to teach the players how to tie lace their shoes to avoid blisters, which meant they’d be more agile on the court because their feet wouldn’t be as sore.

He tried to think of every variable.

After that, he and his team could go into the game with full confidence knowing they gave everything they had, which was the goal, not winning.

Far too many leaders and managers are results-oriented. It’s counterintuitive, but if they were more process-oriented, their teams would get better results. 

 

Become a learning machine

Every single day is an opportunity to be better. As you, the leader, learn more skills, you pass them on to your team and they get more skilled in the process.

It didn’t matter how many games in a row Wooden’s teams won or how many championship banners they hung. He never assumed he knew it all and always kept a “beginner’s mind.” Many leaders get set in their ways, think they know everything, and they resist change. This is why most leaders don’t last. The minute you think you know everything is the minute your path to mediocrity begins.

 

 

“Extreme Ownership: How U.S. Navy SEALs Lead and Win” by Jocko Willink and Leif Babin

This is one of the best leadership books to read because it’s written by leaders who took the most extreme form of leadership possible—leading a group of soldiers into war. Jocko and Leif fought in the Iraq war, mainly the battle of Ramadi, which was one of the most intense and bloody fights in the entire war.

They led a navy seal team, which is the team of the best of the best elite soldiers. You can imagine the type of egos that needed to be managed with a group filled with alpha, type-A, dominant, and aggressive personalities. Also, they had to partner with and train the Iraqi forces, who were unskilled, to fight the Taliban.

On top of this, the Seal team had to deal with urban warfare, fighting in cities with tons of places for enemies to hide. It was hard to tell who the enemy was. A 12-year-old child could be an innocent civilian or a killer (who either wanted to kill U.S. troops or was forced to). In an environment like this, it’s safe to say that top-tier leadership was required.

Jocko went on to teach his leadership principles to businesses. If they’re effective in life-and-death scenarios, imagine how effective they could be in the boardroom.

 

It’s the leader’s fault, always

This is the core premise of the book. If you are the leader of the team, you must take responsibility for the outcomes of the team no matter what.

If there was a miscue that led to one of the troops being killed, Jocko had to own it. Even if the troop himself made the mistake, it could be tied back to a lack of proper training or direction.

If you’re going to lead a team, you have to realize the buck stops with you—always. In corporate settings, there can be a lot of office politics where managers will throw their subordinates under the bus to save themselves. Real leaders, in any setting, fall on their sword.

 

Keep plans simple, clear, and concise

This was essential.

For example, there was a time they planned to clear a territory building by building to find insurgents. Their first plan was to have multiple teams clear multiple buildings at once, but they scrapped it because they realized this could lead to friendly fire.

They refined the plan to make it easy to follow. One team would clear each individual building one by one while the rest of the soldiers would cover that single team’s back.

As a leader, your team needs clarity. Too many leaders make instructions too complicated for no reason. Maybe it’s to appear smart. Maybe it’s because companies and people in general mistake complexity for intelligence, which makes leaders want to show off.

Real leaders don’t care about how they come across. They only care about the team’s performance. They keep plans clear, simple, and easy to understand.

 

Believe in the mission

Teams, and people, want to know where they’re going. They want to know the point, the “why” behind the thing they’re doing. Without it, they won’t give it their all.

A lot of people have criticized the war in Iraq, but as Jocko tells it, the citizens were glad they were there. The mission in Ramadi was to liberate them from an oppressive regime.

Some of the seal team wasn’t enthused about having to train the “lazy” Iraqi soldiers, but Jocko reminded them that training them was part of the broader mission. This inspired them because they were no longer training lazy soldiers; they were doing their part to liberate and stabilize a country in desperate need of both.

 

 

“The Motive” by Patrick Lencioni

This is a book about the difference between real leadership and fake leadership. It’s a book about why most leaders aren’t leaders at all because they like the title of leader more than they embrace the responsibility of leading.

“The Motive” is presented as a business fable, following the story of two CEOs: Shay Davis and Liam Alcott.

Shay Davis is the CEO of Golden Gate Alarm, a home security company. He’s struggling with his role, feeling overwhelmed and unsure about how to lead effectively. His company is underperforming, and he’s considering stepping down.

He seeks advice from Liam Alcott, a successful CEO in the same industry. Liam challenges Shay’s understanding of leadership, pointing out that Shay has been avoiding crucial responsibilities because he’s more motivated by status than he is by responsibility.

Liam introduces Shay to the concept of responsibility-centered leadership, emphasizing the importance of embracing all aspects of the role, not just the ones he likes. Shay changes his ways and the company starts to perform.

You could replace Shay with the vast majority of leaders. I even thought of myself and my company. I lead a small team and a group of students. After reading the book, I saw the ways I was doing only the things I wanted to do, like marketing and content creation, but I was avoiding important tasks like creating SOPs, improving product quality, and doing the deep market and student research required. This book changed my life and my business for the better.

There are many core concepts in the book, but the differences between reward-centered leadership and responsibility-led leadership are enough for an aspiring leader to chew on.

 

Reward-Centered Leadership

• Motivation: These “leaders” are motivated by the benefits of leadership positions—status, power, money, or recognition.
• Behavior: They do the tasks they like and avoid the ones they don’t.
• Focus: They care about their personal success more than the success of the team.
• Approach to work: They delegate critical leadership tasks they dislike, even when they should be the ones doing them.
• Impact: This approach leads to disengaged teams, a lack of accountability, and underperformance.

 

Responsibility-Centered Leadership

• Motivation: These leaders are motivated by duty and a desire to serve.
• Behavior: They take on all aspects of leadership, including the difficult and uncomfortable tasks.
• Focus: The success and well-being of their team members and the overall health of the organization matter more to them than anything else
• Approach to work: They take on the challenging tasks that must be done by them, even if they don’t like them.
• Impact: This approach creates engaged teams, a culture of accountability, and high performance.

 

Responsibility-centered leaders are more effective because they:

1. Develop their people through coaching and feedback
2. Manage subordinates who need to be managed
3. Run great team meetings
4. Communicate constantly and repetitively to employees
5. Place themselves in uncomfortable situations when necessary for the good of the organization

Responsibility-centered leaders view leadership as a duty, not a reward. They understand that their role comes with both privileges and obligations, and they’re willing to embrace both aspects fully.

 

 

The best leadership books teach invaluable skills—use them

Too many people are take a passive role in society. We need more leaders. We need you.

The good news? There’s never been more room at the top.

This doesn’t mean you should seek leadership roles to stroke your ego. It means you should seek them because you have a duty as a human being. 

Don’t let your age prevent you from stepping into roles of leadership. Age doesn’t automatically equal wisdom or the ability to lead. The only skills required are the skills of leadership, which can be learned by anyone at any time at any age.

Now’s the best time to start.

 

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