6 of the best leadership books to help you get ahead

Leadership. The topic everyone knows a little about but can’t quite agree on. We’ve all had a great boss at some point in our lives, but pinning down what it was we liked about them can be a challenge. To complicate matters, great leaders come in all shapes and sizes, meaning that leadership skills don’t always translate to Fortune 500 notoriety.

The scholarship surrounding good leadership isn’t particularly vast, but there are a few constants as to what makes someone easier to follow. Leaders are good communicators, positive in their outlook, and willing to compromise when necessary. They have at least some emotional intelligence. But are these traits innate?

Can entrepreneurs expect to succeed if they don’t already possess these skills, or can anyone learn to be a good leader? According to the most renowned leadership authors, the answer to the latter question is yes. If you’re willing to put in some time and effort, you can become a great leader.

Let’s take a look at six of the best leadership books of all time that can help you develop the skills you need to better lead a team.

Dare to Lead – Brené Brown

If you’re not familiar with bestselling author Brené Brown, she is a researcher at the University of Houston whose work focuses on self-empowerment, and she has been immensely influential in the discourse of self-love and courage in the business world. Dare to Lead is a must-read that takes readers on a journey to get honest with ourselves and really ask what each of us needs to show up and do the work.


Brown argues that great leadership means proactively acknowledging and addressing the fears and feelings that come with change, without spending too much time simply managing problematic behaviors, which can lead to a loss of trust and connection in the process.

Brown encourages readers to focus on becoming more emotionally vulnerable (eek!) by identifying what they value in relationships and entrusting others with that information. Only real, profound interhuman connection can foster loyalty and commitment.

The book is laid out into four sections:

  • Rumbling with Vulnerability. It’s natural to protect oneself—especially in positions of leadership—but the unwillingness to be genuine, sincere, and vulnerable can create a culture of defensiveness and fear. Brown provides a dictionary of emotionally protective mechanisms that get in the way of gaining your teams’ trust. It also offers suggestions for how business leaders can take inventory of themselves and improve.
  • Living Into Your Values. Do you know who or what actually matters to you? How much are your decisions influenced by what you think others expect? In this section of the book, Brown encourages readers to trust themselves with difficult decisions and embrace the power of knowing what’s right for them personally.
  • Braving Trust. You can’t be an effective leader without delegating to others from time to time. Readers apply the same lessons they learned about themselves to others, giving them the space they need to exercise strength and find answers. This mutual environment of vulnerability creates teams that want to support each other.
  • Learning to Rise. Keeping a cool head when everyone else is losing theirs is a hallmark of the best leaders. Theory is great and all, but rational thinking isn’t exactly the first thing that comes to mind when you’re drowning in the throes of fear. Brown tackles this by helping readers identify their own fear triggers so they can practice stepping back and thinking constructively when things get rough.

Brown’s business books are available online, but her website has some free resources to explore if you can’t wait to buy the book. Let’s get vulnerable.

Start with WHY – Simon Sinek

leadership-books-450x350px-1No list of the best leadership books would be complete without Simon Sinek. His book titles are microlessons in themselves—Leaders Eat Last, Together Is Better, Find Your Why—so it’s no wonder that Start with WHY is considered one of the great books on how leadership roles lead teams to success.

Sinek has a fairly binary view of most issues surrounding leadership styles: micromanage to get a result or step back to let everything fall into place, inspire carrots or manipulate sticks, limbic system or neocortex, etc. For those looking for a foundation, these black-and-white comparisons help to illustrate a concrete understanding of what great leaders do.

In essence, Start with WHY is about personal development: What is it that truly motivates us at a base, reptilian level? Once we know why we’re working for something, the how and the what come naturally.

Successful leaders follow a natural pattern without expecting unreasonable results. One example Sinek uses is Volkswagen, which got its start in consumer cars by being the people’s car—an affordable, reliable product built to last. At one point, however, VW decided to dabble in luxury cars with their expensive Phaeton model. Because they lost their why, Sinek says, they sold nothing and (wisely) returned to their original business model.

Companies that understand why they are in business are more stable and grounded, placing heavy emphasis on the creation of a meaningful mission statement. Teams that understand the importance of what they’re doing show up to work and perform well. If you’re wondering how to be a better leader, ask yourself what would happen if your team were to disappear. Where would the company or its customer base suffer? Knowing the answer may help you find your ‘why’. Learn more by checking out Sinek’s lecture.

Tuckman’s Stages of Group Development

Ok, this isn’t a management book per se, but it is a crucial roadmap for understanding how teams work, which is essential for effective leadership. Bruce Tuckman was a psychology researcher whose work focused on the work habits of groups and individuals. His theory on the development, functions, and dysfunctions of a team is taught in universities worldwide because of its timeless relevance in getting people to work together.

According to Tuckman, new leaders need to understand that every working group undergoes four (or five) stages as they reach the completion of a given project:

  1. Forming. People come together with a common goal. Personalities find their natural fit in the group as relationships bud. Objectives are outlined regarding the group’s intentions and each team member’s responsibilities. Most work is done independently at this stage.
  2. Storming. As trust is gained among team members, more voice their opinions and attempt to establish power and status, often leading to disagreement and personality clashes. Effective groups suffer fewer incidents, but those caught in disagreement must minimize the damage and move on as quickly as possible. Tolerance and patience are important virtues at this stage.
  3. Norming As team members learn to accept each other, a spirit of cooperation emerges. They recognize their common goal and identify competition they face outside the group. Ideally, team members continue to share their unique ideas, but even here, fear of dissent can prevent people from doing so.
  4. Performing Success starts to happen, sometimes beyond what anyone expected. Roles are understood and decisions can be made without supervision.

Since Tuckman published his theory, others have appended it with helpful ideas about picking teams that have a better chance at success. According to one healthcare research study, Tuckman’s leadership lessons are best put into practice when leaders take the following steps:

  • Pick team members with purpose.
  • Identify team goals.
  • Encourage the development of a shared mental model.
  • Coach your team when disagreements and biases arise.
  • Engender mutual trust.
  • Keep the work environment calm.
  • Encourage feedback from staff.
  • Provide a route to transfer leadership.
  • Set aside time to plan for and engage the team.
  • Allow team roles to be flexible.
  • Carefully select new team members.
  • Provide future leadership opportunities.

Tuckman’s invaluable insights on setting teams up for success offer a clear path forward for startups. Like the constant gardener, leaders must keep a watchful eye on their teams without influencing their decisions too hastily.

How to Win Friends and Influence People – Dale Carnegie

Perhaps one of the most clinical books about productive relationships and shared goals is this timeless manual by Dale Carnegie. It’s a short read, and highly effective in delivering its message of how to convey courage and stoutness. Just reading it imparts a kind of unapologetic shamelessness we can all benefit from.

leadership-books-450x350px-2Start with your appearance, Carnegie says. Dressing sharply and maintaining personal hygiene is like wearing a costume that says, “you can trust me.” It goes beyond brushed teeth and clean clothes to include regular car washes, tidy kitchens, and empty laundry hampers. Is it exactly what one expects from good leaders? Maybe not, but it’s hard to find much fault with the philosophy.

Are you monitoring your body language? If not, you may be conveying messages of defensiveness, fear, or apathy that do not engender trust to your team members. Stand up straight, offer firm handshakes, and keep smiling.

Want to improve your conversational abilities? Carnegie suggests reading the classics. Shakespeare can teach you all about human nature so that during your next performance review, you’ll have a better foundation to understand your team members and a better vocabulary to express your ideas.

In this author’s opinion, the best nugget of Carnegie’s advice is adopting the language of agreeability—focusing more on the “I” than the “you” when expressing emotion so as to create a space where others can share their own personality.

It’s a good book, as far as self-help goes.

Good to Great: Why Some Companies Make the Leap… and Others Don’t – Jim Collins

Like Simon Sinek, Jim Collins understands the value of a stark comparison. In Good to Great, Collins highlights real-life examples of companies that succeed by comparing them to their unremembered peers and examining the differences. The author upends some of the conventional wisdom surrounding soaring corporate success—growth via acquisitions, disruption, and stock options—to illustrate a more mathematical model: mass times velocity.

Focus on creating an airtight philosophy that is easy to adopt, then get employees to adopt it and witness amazing results. Collins uses the example of Kroger, where 50,000 employees embraced a new company strategy and moved forward together, resulting in massive growth. Similar to Sinek’s idea, this only happens when people understand the ultimate destination, rather than who will get them there.

Collins’ wants leaders to stop doing unproductive things. If you’re not getting anywhere, cut your losses quickly and turn your efforts toward where they can do something that matters.

The 21 Irrefutable Laws of Leadership: Follow Them and People Will Follow You – John C. Maxwell

So far, the aforementioned texts focus on how leaders can harness the motivations of their teams. But what are the actual traits of good leaders? In John C. Maxwell’s The 21 Irrefutable Laws of Leadership, we get a portrait of who keeps the wheels turning. More than anything, this massive bestseller offers a visualization of what leadership looks like to give hopeful leaders a role model to strive toward, though it is a bit dated.

According to Maxwell, leaders alone set the limits for what kind of results to expect. If the company isn’t skyrocketing to meteoric heights, it’s because a manager is hurting their team’s chances for success, which means it’s time to fire that manager and find someone more inspiring.

Can anyone disagree with this approach? Perhaps, but Microsoft, SpaceX, Comcast, Goldman Sachs, Walmart, and countless other Fortune 500 companies operate on this exact principle: if someone isn’t getting results, cut ‘em loose and put out the fire before it spreads. Find a leader who fits the profile and trust them.

And what are the 21 irrefutable laws of leadership? They are as follows:

  1. The Law of the Lid. Teams can only rise to the level of their leaders.
  2. The Law of Influence. At their core, leaders are nothing more than influence.
  3. The Law of Process. Greatness takes time. Be patient.
  4. The Law of Navigation. Use your goals to look ahead.
  5. The Law of Addition. Help others grow through praise and trust.
  6. The Law of Solid Ground. Be candid, honest, and committed to your values.
  7. The Law of Respect. The respect you show to others will be shown to you.
  8. The Law of Intuition. Know which play to call when the moment comes.
  9. The Law of Magnetism. Surround yourself with high-quality people.
  10. The Law of Connection. Develop strong bonds with team members.
  11. The Law of the Inner Circle. Draw strength from people you admire.
  12. The Law of Empowerment. Don’t control. Empower others.
  13. The Law of the Picture. Continuously communicate your goal of a better future.
  14. The Law of Buy-In. Help people care about what you want to do.
  15. The Law of Victory. Never accept defeat.
  16. The Law of the Big Mo. Celebrate all small wins to build momentum.
  17. The Law of Priorities. Addressing priorities are more important than keeping busy.
  18. The Law of Sacrifice. Learn to face the dangers of reaching your goals.
  19. The Law of Timing. Be patient, and trust your intuition.
  20. The Law of Explosive Growth. Find the leaders in your team and lead them.
  21. The Law of Legacy. The present determines the past, so create a succession plan.

Maxwell’s book is about what it looks like when leaders instill a vision in others, no matter the cost.

In Conclusion

There’s a cliché out there that good bosses can’t be both a friend and a manager, but the books listed in this blog prove there’s more to the conversation. Leadership is about meeting workers where they are and creating clear expectations. It is not about being the best or the most senior, but about creating an environment where people feel good about the work they do so they can contribute to the best of their ability. The better they feel about themselves, the better the work that gets done.