These Books Made Me a Better Leader
For project managers who want to build something greater than themselves.
👋 Hey, Kyle here! Welcome to The Influential Project Manager, a weekly newsletter covering the essentials of successful project leadership.
Today’s Overview:
People think that leadership is something that just happens. You’re promoted to it. Born into it. Anointed by someone else.
But anyone can be a leader and everyone should learn how to be one–of families, of companies, of a team, of an audience, of a group of friends, of ourselves.
These 16 books changed how I lead. This summary might do the same for you.
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DEEP DIVE
📚 These Books Made Me a Better Leader
Filed under: Leadership & Managing People
People think that leadership is something that just happens.
You’re promoted to it. Born into it. Anointed by someone else.
We think, “I’m not a leader—I just manage projects, teams, maybe myself.”
But anyone can be a leader and everyone should learn how to be one–of families, of companies, of a team, of an audience, of a group of friends, of ourselves. There’s no one who wouldn’t benefit from learning from some of history’s greatest leaders.
If there’s one thing that’s helped me lead better, it’s reading. Real leadership isn’t flashy. It’s built through experience, failure, and learning from people smarter than you.
Which brings us to this week’s newsletter, where I wanted to recommend some of my favorite books about leadership.
Over the years, I've read over 100 nonfiction books on leadership, strategy, and managing people. And I’ll be honest—most weren’t worth it. Some should’ve been blog posts. Some didn’t apply to the real world.
But a handful changed how I lead teams, manage projects, and grow personally. Maybe they’ll do the same for you.
Read on for my notes on all 16—and find your next good read.
1. How to Be a Leader: An Ancient Guide to Wise Leadership
Author: Plutarch
Leadership advice doesn't get more battle-tested than this. The Stoics talked over and over again about how studying the lives of the “greats” is one of the best ways to learn. Studying their flaws, their virtues, their strategies, and their failures. Plutarch took that lesson to heart.
What struck me was his balanced approach. He didn't just highlight Caesar's strategic brilliance but also his fatal ego. Cicero's persuasive eloquence alongside his blinding vanity. Cato's iron discipline paired with his self-destructive stubbornness.
It’s also worth noting that he wasn’t just a mere writer, but a leader himself. Reading this reminded me: the best leaders don’t just study wins. They study what not to do, too.
Favorite quotes:
“A leader cannot straighten what is crooked in others until he has straightened himself first. It's like trying to build on a faulty foundation—the structure will never stand. The ungoverned cannot govern; the disordered cannot create order. First master yourself, then lead others.”
2. The Five Dysfunctions of a Team: A Leadership Fable
Author: Patrick Lencioni
This book is essential for anyone who is part of a team or leads a team. When your team isn't clicking, it's rarely about personalities. It's about dysfunction at a structural level:
Lack of trust.
Fear of conflict.
No commitment.
No accountability.
Ignoring results.
Every team will struggle if they do not apply the principles of building trust and employing healthy conflict. It’s hard to believe, but the answer to how we can be a good team is simple and contained in this book. You don’t need a new team. You need a new approach.
Favorite Quotes:
“Great teams do not hold back with one another. They are unafraid to air their dirty laundry. They admit their mistakes, their weaknesses, and their concerns without fear of reprisal.”
3. Antifragile: Things That Gain from Disorder
Author: Nassim Nicholas Taleb
Things that are antifragile benefit from randomness, uncertainty, and variation.
Life and project management is messy and seemingly getting messier. Can we position ourselves to gain from this disorder … to not only recover from mistakes but get stronger?
The answer is yes. There are principles we can follow to help us. Nassim Taleb has some excellent thoughts on how to live an antifragile life, giving us these core principles taken from his book:
Stick to simple rules
Build in redundancy and layers (no single point of failure)
Resist the urge to suppress randomness
Make sure that you have your soul in the game
Experiment and tinker — take lots of small risks
Avoid risks that, if lost, would wipe you out completely
Don’t get consumed by data
Keep your options open
Focus more on avoiding things that don’t work than trying to find out what does work
Respect the old — look for habits and rules that have been around for a long time
In short, stop optimizing for today or tomorrow and start playing the long game.
Favorite Quotes:
“Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk, and uncertainty. Yet, in spite of the ubiquity of the phenomenon, there is no word for the exact opposite of fragile. Let us call it antifragile. Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better. This property is behind everything that has changed with time: evolution, culture, ideas, revolutions, political systems, technological innovation, cultural and economic success, corporate survival, good recipes (say, chicken soup or steak tartare with a drop of cognac), the rise of cities, cultures, legal systems, equatorial forests, bacterial resistance … even our own existence as a species on this planet.”
4. How Big Things Get Done: The Surprising Factors That Determine the Fate of Every Project
Authors: Prof. Bent Flyvbjerg & Dan Gardner
This is practically the project manager's bible. Flyvbjerg analyzed thousands of large projects worldwide and discovered why 90% of megaprojects fail: we rush, over-plan, and get overconfident.
The solution isn't working harder. It's working smarter:
Go small before going big (prototype and test extensively)
Think slow, then act fast (deliberate planning, decisive execution)
Plan for learning, not perfection (expect and embrace course corrections)
In construction specifically, this book saved my company millions by changing how we approach project planning.
Favorite Quotes:
“Abraham Lincoln is reputed to have said that if he had five minutes to chop down a tree, he’d spend the first three sharpening the axe. That’s exactly the right approach for big projects: Put enormous care and effort into planning to ensure that delivery is smooth and swift. Think slow, act fast: That’s the secret of success.”
5. The Captain Class: A New Theory of Leadership
Author: Sam Walker
What a book! It proves that we have really missed what makes great teams and organizations work. It’s not star players, it’s not even how much they can spend. Walker’s research proves the world’s most dominant teams had one thing in common—a gritty, relentless, low-ego captain.
Athletes like Bill Cartwright of the Chicago Bulls, Carla Overbeck on the U.S. Women’s Soccer team, Yogi Berra of the New York Yankees and Jack Lambert of the Pittsburgh Steelers were not by any means the most famous or the most talented players, but they were the glue that held the team together.
I think this is a incredibly well-written book should be studied by anyone trying to build a great organization (or trying to find a role for themselves inside one).
Favorite Quotes:
“One of the great paradoxes of management is that the people who pursue leadership positions most ardently are often the wrong people for the job. They're motivated by the prestige the role conveys rather than a desire to promote the goals and values of the organization.”
“THE SEVEN TRAITS OF ELITE CAPTAINS 1. Extreme doggedness and focus in competition. 2. Aggressive play that tests the limits of the rules. 3. A willingness to do thankless jobs in the shadows. 4. A low-key, practical, and democratic communication style. 5. Motivates others with passionate nonverbal displays. 6. Strong convictions and the courage to stand apart. 7. Ironclad emotional control.”
6. Team of Teams: New Rules of Engagement for a Complex World
Author: General Stanley McChrystal
Managing today's complex projects with yesterday's command-and-control approach is like trying to use a rotary phone in the smartphone era.
McChrystal transformed how the military operates in complex environments, and his lessons translate perfectly to business:
Shared consciousness (everyone understands the big picture)
Empowered execution (teams can make decisions without waiting for approval)
Transparency (information flows freely across departments)
This book is about letting go of control, trusting your people, and building teams that think fast and act faster.
Favorite Quotes:
"In today's complex world, trying to manage every detail from the top is like trying to direct a symphony through binoculars from a helicopter. You can't possibly see everything that matters. Instead, you must create a team where everyone understands the mission so deeply that they'll make the right call even when you're not there. That's when you've built something truly powerful—not just a project, but a team of teams."
7. Traction: Get a Grip on Your Business
Author: Gino Wickman
Want to run a business or a project that doesn’t run you ragged? Traction is your blueprint.
What makes this book stand out is its practical tools and applications. I've borrowed multiple systems from EOS (Entrepreneurial Operating System) and adapted them for my work:
The 90-Day World: Breaking massive goals into 90-day sprints
Level 10 Meetings: The most efficient team meetings you'll ever run
The Accountability Chart: Clarifying who owns what (no more "not my job")
The People Analyzer: Making sure you have the right people in the right roles
These tools have transformed how we operate and brought unprecedented clarity to my project teams.
Favorite Quotes:
“An Integrator is a person who has the Unique Ability® to harmoniously integrate the major functions of the business, run the organization, and manage the day-to-day issues that arise. The Integrator is the glue that holds the people, processes, systems, priorities, and strategy of the company together.”
8. The New One Minute Manager
Authors: Ken Blanchard & Spencer Johnson
The New One Minute Manager is an update of a classic, and it’s a stellar guide to effective communication between managers/bosses and their employees.In today's fast-paced world, time is money. This book showed me how to lead effectively in 60-second bursts:
One-minute goals (crystal clear expectations)
One-minute praisings (immediate positive feedback)
One-minute redirects (course corrections without drama)
Instead of hour-long lectures or waiting for quarterly reviews, I started giving feedback in the moment—and it revolutionized team performance.
Favorite quotes:
“If you can’t tell me what you’d like to be happening, you don’t have a problem yet. You’re just complaining. A problem only exists if there is a difference between what is actually happening and what you desire to be happening.”
“We are not just our behavior. We are the person managing our behavior.”
9. The Laws of Human Nature
Author: Robert Greene
This book is just as full of life knowledge as his others, and even easier to apply to real life.
I didn’t like this book on initial read as much as Greene’s other books (and he’s one of my favorite authors). It is dense and will be long to get through initially, but it will be worth it.
Full of lessons on psychology and strategy that will help you in work, relationships and life.
Favorite Quote:
“When choosing people to work and associate with, do not be mesmerized by their reputation or taken in by the surface image they try to project. Instead, train yourself to look deep within them and see their character. A person of strong character is like gold—rare but invaluable. They can adapt, learn, and improve themselves.”
10. The 48 Laws of Power
Author: Robert Greene
Look, if you think the point of this book is to make you into a ruthless killer and tyrant, you are not reading it right.
The point is that human beings have been striving for power, putting up against powerful interests, trying to create change or build institutions for as long as there has been such a thing as society.
A few lessons have been learned along the way…and more than a few patterns have emerged. You’re not being smart if you don’t try to familiarize yourself with them. You will also have a hard time if you ignore them because it increases the chances that you will be a victim of these forces and lessons.
Know the rules. Play them wisely.
Favorite Quote:
“When you are trying to impress people with words, the more you say, the more common you appear, and the less in control. Even if you are saying something banal, it will seem original if you make it vague, open-ended, and sphinxlike. Powerful people impress and intimidate by saying less. The more you say, the more likely you are to say something foolish.”
11. Extreme Ownership: How U.S. Navy SEALS Lead and Win
Authors: Jocko Willink & Leif Babin
This book hit me like a ton of bricks. If you have ever struggled with any form of a victim mentality, consider reading this book. Jocko provides examples from his experience on deployment about how to be accountable, own the mission, and move forward as a competent team leader.
The core message? You own everything in your world.
Your project’s a mess? That’s on you.
Your team’s not performing? That’s on you.
Things going great? That’s also on you.
Instead of looking for someone to blame, you ask, "What could I have done differently?"
Favorite Quotes:
“For all the definitions, descriptions, and characterizations of leaders, there are only two that matter: effective and ineffective. Effective leaders lead successful teams that accomplish their mission and win. Ineffective leaders do not.”
“On any team, in any organization, all responsibility for success and failure rests with the leader. The leader must own everything in his or her world. There is no one else to blame. The leader must acknowledge mistakes and admit failures, take ownership of them, and develop a plan to win.”
12. Switch: How to Change Things When Change is Hard
Authors: Chip & Dan Heath
Switch was written to help people with implementation. If you have already learned the art of dealing with people, the next step is to find safe and effective ways to lead individuals and groups through the process of change.
Change is hard because people are complicated. The authors use the analogy of a Rider (rational mind), an Elephant (emotional side), and a Path (environment) to explain why change is so difficult and how to make it happen:
Direct the Rider: Give clear, specific direction (not "be more efficient" but "use this exact process")
Motivate the Elephant: Appeal to emotion (share stories of success from the new approach)
Shape the Path: Make the new behavior easier than the old one (remove obstacles to adoption)
This framework has helped me successfully implement everything from new software to enhanced safety cultures.
Favorite Quotes:
"Today, as you go through your day, notice how many times people have tweaked the environment to shape your behavior…If you change the path, you’ll change the behavior."
13. Trillion Dollar Coach: The Leadership Playbook of Silicon Valley's Bill Campbell
Authors: Eric Schmidt, Jonathan Rosenberg, and Alan Eagle
Even the best athletes have a coach. Tom Brady. Tiger Woods. Caitlin Clark. They are a product of their coaches. And so it goes with leaders. They have mentors. They have boards of advisors. They have leadership coaches.
As it happens, Bill Campbell was for many years a football coach–at Columbia University–and then he started coaching upcoming entrepreneurs like Steve Jobs, Larry Page, and Eric Schmidt. He played an instrumental role in the growth of companies like Google, Apple, and Intuit.
This book revealed something I'd been missing: no matter how experienced you become, you need outside perspective. Now I meet regularly with a community that challenges my thinking and helps me see blind spots.
Favorite Quotes:
On the importance of coaching: “Coaching is no longer a speciality; you cannot be a good manager without being a good coach.”
Team first: “Work the team, then the problem”
On Servant Leadership: “If you’re a great manager, your people will make you a leader. They acclaim that, not you.”
On Meritocracy: “He believed in striving for the best idea, not consensus.”
On Decision-making: “Make the best decision you can, then move on.”
14. The Wisdom of the Bullfrog: Leadership Made Simple (But Not Easy)
Author: William H. McRaven
Admiral McRaven’s books are just great, tight, well-done books. I guess we shouldn’t expect anything less from a Navy SEAL.
It’s so easy to sneer at mottos and credos—“Expect what you inspect”, “Who dares wins”, “No plan survives contact with the enemy”, “The only easy day was yesterday”—but then you meet high performers, be they athletes or Special Forces Operators or CEOs, and you find they take these seriously. Like very seriously! If you can get over your cynicism, this earnestness is infectious and inspiring.
You find that at the highest levels and with the most difficult jobs, they find ways to boil things down to their essence. Anyway, McRaven’s books are largely meditations on a series of those simple ideas and I think most people would be better off for reading them.
Favorite Quote:
“Whenever I had a difficult decision to make, I would ask myself, “Can you stand before the long green table?” Translation: can you justify the decision and explain what drove the decision-making process.”
15. Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones
Author: James Clear
Leadership isn't about grand speeches or heroic moments. It's about what you do every single day.
Small habits, consistently applied, create massive outcomes over time:
Daily team check-ins become high-trust environments
Weekly reviews prevent months of misalignment
Regular recognition builds unstoppable culture
Systems beat goals every time. A goal is hitting your target. A system is your daily and weekly routines that make hitting that target inevitable.
Favorite quotes:
“Your outcomes are a lagging measure of your habits. Your net worth is a lagging measure of your financial habits. Your weight is a lagging measure of your eating habits. Your knowledge is a lagging measure of your learning habits. Your clutter is a lagging measure of your cleaning habits. You get what you repeat.”
“You don’t rise to the level of your goals. You fall to the level of your systems.”
16. Mindset: The New Psychology of Success
Author: Carol Dweck
There are two types of leaders:
Fixed mindset: "That's just how we've always done it."
Growth mindset: "Let's try a better approach."
Dweck's research shows that your mindset—fixed or growth—determines almost everything about your success. Leaders with fixed mindsets fear failure, avoid challenges, and resist feedback. Those with growth mindsets seek challenges, learn from criticism, and view failure as temporary.
Favorite Quotes:
“Mindsets aren't permanent. Like intelligence and skill, they're not something that one is necessarily born with. Because of that, they can be changed. This is great news for people who want to develop a growth mindset. It's also a warning for people who already have a growth mindset or are trying to foster one in a child. Outside influences, such as feedback and expectations from authority figures, can shift a growth mindset to a fixed mindset. The lesson is to be aware of one's growth mindset and consciously practice using it, even when it doesn't seem necessary.”
Conclusion
Better readers make better leaders. And better leaders deliver better projects.
You don't need to read all 100+ books I've consumed over the years. Just start with one or two from this list that speak to your current challenges. Let them shape how you think, lead, and build.
I treat reading like a job. Because it’s the only job that gives me better tools to lead, grow, and deliver. Enjoy these books, treat your education like the job that it is, and let me know if you ever need anything.
What are your favorite strategy, leadership, and management books? Hit reply—I’m always looking for the next one.
Until next week,
Kyle Nitchen
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Great list. A few are my favorites too. A couple others I've added to my to-read.
This is a great list, especially since it features one of the books that are foundational for my work (antifragile) and because it has some new names that I’ll check out ! Thanks