Leadership: What Does it Mean?

Someone in my accountability group asked me to recommend the three best books on leadership. My first question to him was, “What kind of leadership are we talking here?”

To me, there are three types of leadership:

• leading yourself (a.k.a., professional self-development)
• leading others
• leading an organization.

When we search for “leadership books” on Amazon we’ll find over 50,000 book titles. To answer my colleague’s questions, I promised myself I’d list only five that immediately leap to my mind. Here’s what I’d consider the best books on leadership for each of those subcategories.  

Leading yourself

Leading yourself is a prerequisite for leading other people or organizations.

In fact, a research study commissioned by Cornell University showed that organizations are more likely to be successful when the boss has superior self-awareness.

My conclusion: Your endeavor or your organization will only grow as fast as you are growing.

In short, think of this as the personal level of leadership.

Limiting myself to the five that leap to my mind, I’d name these books which hugely impacted me:

1. The Road Back to You by Ian Morgan Cron and Suzanne Stabile
2. Mindset: The New Psychology of Success by Carol Dweck
3. Start with Why: How Great Leaders Inspire Everyone to Take Action  by Simon Sinek
4. Feel the Fear and Do It Anyway® by Susan Jeffers
5. The Laws of Lifetime Growth: Always Make Your Future Bigger Than Your Past by Dan Sullivan and Catherine Nomura

I’m also a big believer that focusing on our strengths gives us a higher-yield result than trying to overcome our weaknesses. So as I think about the best books on leadership I want to mention Go Put Your Strengths to Work: 6 Powerful Steps to Achieve Outstanding Performance by Marcus Buckingham.

Leading people, or leading a team

If you’re a solopreneur, you might not think of yourself as a “leader.” Please, think again.

As a solopreneur, you might have a part-time assistant, or a spouse who helps with administrative issues. You may assume that having only person — paid or not — doesn’t technically qualify as a “team,” but that person does look for leadership.

And, as a solopreneur, you’re leading people toward a deal (i.e., a contract), or sale of products or services. But eventually, your project, the business, or the department grows, right?  

In short, think of this as the interpersonal level of leadership.

If you’re a boss with a team, or if you’re teaching, coaching, or counseling, I think it’s fair to say that these are among the best books on leadership.

1. Crucial Conversations: Tools for Talking When Stakes Are High by Kerry Patterson and others
2. The Five Dysfunctions of a Team: A Leadership Fable by Patrick Lencioni
3. The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever by Michael Bungay Stainer
4. Change Your Questions, Change Your Life: 12 Powerful Tools for Leadership, Coaching, and Life by Marilee Adams
5. Wooden on Leadership by John Wooden

Having spent most of my hospital career hearing, “that’s the way we’ve always done it,” I’m eager to suggest Beyond the Wall of Resistance by Rick Maurer if your team often resists change.

So, although you lead a team that works within an organization, the interpersonal level of leadership is more about your interactions to foster growth for the individuals on that team.

Leading organizations

If you’re the leader of an organization — any organization, great or small, whether it’s the Rotary Club, your own small business, or a Fortune 500 company — you’ll need to master your role in leading the organization as a whole.

Where is it going, i.e., can you see your North Star? How can you carry out your mission?

In short, think of this as the system level of leadership. Not just me, but I’ve heard many others identify these books as being among the best books on leadership.

1. Good to Great: Why Some Companies Make the Leap and Others Don’t by Jim Collins
2. The Vision Driven Leader by Michael Hyatt
3. Leading Change by John P. Kotter
4. The Four Disciplines of Execution by Chris McChesney and others
5. The 21 Irrefutable Laws of Leadership by John C. Maxwell

If you’re similar to my group of entrepreneurs, owners of small businesses, or directors of groups, you’ll need to read books well beyond just “leadership.”

In his book, Business Made Simple, Donald Miller says that a business has six main components that are analogous to an airplane. So, if you’re in business, the books I just listed are related to only the “cockpit”. You’ll still need to read about the other five components of your business.

1. Cockpit (leadership)
2. Right engine (marketing)
3. Left engine (sales)
4. Wings (products and services)
5. Body (overhead, i.e., salaries, benefits, rent, office supplies, etc.)
6. Fuel (finance)

Notice that Miller’s model doesn’t address such topics as project management, product creation, conflict management, emotional intelligence, decision-making, productivity, delegation, problem-solving, focus, or other skills which successful leaders will need to master. Here are a few books that you might find helpful:

Atomic Habits by James Clear

Decisive by Chip and Dan Heath

Emotional Intelligence by Daniel Goleman

Profit First by Mike Michalowicz

The Bravest You by Adam Kirk Smith

The CEO Next Door by Elena Betelho and Kim Powell

The ONE Thing by Gary Keller

The Reputation Game by David Waller and Rupert Younger

Traction by Gino Wickman

Willpower Doesn’t Work by Benjamin Hardy

Before searching for the best books on leadership on “leadership,” decide if you need help leading at the personal, interpersonal, or system level, and identify what problem you’re trying to solve.

What would you name as the best books on leadership? Let me know in the comments below!