The Graduate Degree in Leadership Reading List

You can read about this on my substack.

The below is my core curriculum for the aspiring leader, manager, parent, teacher, or figure of authority who wants to be better than they were yesterday. This is a non-exhaustive list of the media I recommend for anyone aspiring to be better.

Learning rounds us out and shows us what can be better. Whenever I’ve been in a tough position at work, life, and so on, I’ve escaped to audiobooks and podcasts to learn about how to make things better.

Leadership vitruvean man leonardo da vinci. Ancient texts and leadership.

The harder part, applying what you learn, comes next. It’s possible, though, and I’ve achieved all my aggressive career goals and have started a company, Kestryl Edge LLC, based on what I’ve learned and practiced from the materials below.

So! I recommend the below Books, Podcasts, and Shows to anyone wanting to elevate their career and “Sharpen the Saw.” Learning never stops!

Disagree with my curriculum? Have an addition? Great.

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The Books

The E-Myth Revisited by Michael E. Gerber

Essential read for anyone wanting to start a business. It is important to read to understand the modes of failure for small companies and startup ventures.

Extreme Ownership by Jocko Willink and Leif Babin

A powerful book on mindset for leadership. A perfect first stop for anyone wanting to become a leader in any capacity. A book I’ve read and re-read. (Willink and Babin 2015)

Start with Why by Simon Sinek

The title says it all, but the book is worth the read to understand the principle and its applications. As teams look at trust building, raising EQ, and building leadership chops, so much of it comes back to Why. (Sinek 2009)

Leaders Eat Last by Simon Sinek

A great read on leadership for learning how to build psychological safety and trust in the workplace. It contains strong chapters arguing for the development of empathy in the workplace. It is a perfect read for those wanting to learn about culture building.

The Power of Vulnerability by Brené Brown

Awesome listen on Audible, very entertaining, and very moving. A perfect first read for those who are emotionally illiterate. It is a great primer on shame and professional vulnerability.

How to Win Friends and Influence People by Dale Carnegie

The archetypal “How to People” book. It covers how to be liked, how to get along well with others, and how to build relationships that work.

The Stormlight Archive by Brandon Sanderson

A five-part series that has nothing and everything to do with management, leadership, and perseverance. We learn about how to be from story and characters. The characters in Stormlight Archive reinforce the leadership lessons we learn from the non-fiction books. In the workplace, be a Dalinar, a Navani, or an Adolin.

Meditations by Marcus Aurelius

A quick and thought-provoking journal of a Roman emperor that can teach us how to remain steady in chaos. This one is great for the hot tub or the camping trip where you have some quiet to reflect and let it sink in.

Never Split the Difference by Christopher Voss and Tahl Raz

Awesome book for building confidence in tense discourse. People need to negotiate all the time, and this book provides practical tools and useful tips on how to negotiate successfully. Talking to the difficult coworker? Useful book. Talking to your boss? Useful book.

7 Habits of Highly Effective People by Stephen Covey

If you have your routines down pat, you may not need this. Routines and habits are what we build on to make long-term projects possible. If you don’t have a routine and feel like you are a slave to your calendar and your obligations, then this is a great book for you.

How to Have Willpower: An Ancient Guide to Not Giving In by Plutarch and Prudentius

Sure, there are plenty of books out there about willpower and perseverance, and this one is more of a collection of essays by Plutarch and Prudentius. This is less about hacks and more about principles you want to carve into your very being. Reading this book won’t magically grant you ironclad willpower, but taking the messages to heart and practicing the principles, over time, will.

Radical Candor by Kim Scott

I would put this in the required reading for college if I could. This is one of the best management books out there right now in terms of message, tools, and guidance. If you ever touch management roles and responsibilities, read and implement the lessons in Radical Candor. You’ll learn how to be direct without burning the house to the ground. You’ll learn key systems to building trust and rapport on a team, and much more. Buy, buy, buy!

Legacy by James Kerr

My college rowing coach had us read this rugby book together, and I think it was a formative book in terms of learning the mindset of successful team building and what it means to be great. It’s an awesome book on emotional control, sustained excellence, and relentless cultural standards. If the jackasses who are in the news are the problem with leadership and management today, then this is the cure.

The Art of War by Sun Tzu

A book that is more philosophy than warmaking how-to. The messages are clear, timeless, useful, and adaptable to most endeavors in life. This gets put on a lot of “Bro’s” must-reads for “Utter Dominance in the Manly Workplace,” which is why it can get a mixed wrap in the leadership space. My position is that if anything is controversial, you should read it and form your own opinion. You’re a leader, think for yourself. Do I think you need to approach your HR conversation with a war plan based around speed and deception? Haha, no, I don’t. Check it out; this book is a classic.

48 Laws of Power by Robert Greene

The unfortunate reality of the workplace is that your coworkers and bosses aren’t going to be Brené Brown, Jocko Willink, Simon Sinek, and Kim Scott. They’re going to be Ted from accounting and Cindy from projects. Politics, power, and manipulation are everywhere in the workplace.

My approach to this class is the same as Professor Lupin and Mad-Eye Moody as Defense Against the Dark Arts teachers. Better to know what you’re up against than to be caught Winnie the Pooh style and succumb to some numb nuts who wants to be important for the day and get in your team’s way. I’m a proponent of collaboration and the How to Win Friends and Influence People methods of getting shit done. Unfortunately, workplace bullies exist everywhere. So check out 48 Laws of Power as a research into how power works and stay allegorically strapped.

To Kill a Mockingbird by Harper Lee

Integrity matters, and doing the right thing can demand a price. Empathy is strength and prejudice is corrosive. This is one I come back to every so often.

Man’s Search for Meaning by Viktor Frankl

A transformative read on meaning, suffering, and survival. Knowing your “Why” allows you to survive the most difficult “Hows.”

If you know Why, you can bear almost any How.

Outliers by Malcolm Gladwell

I think this is in the high school reading curriculum now, which is great. A solid read on how timing, culture, opportunity, practice, and hidden advantages play a huge role in one’s success. This is where the 10,000-hour rule comes from.

The Prince by Niccolò Machiavelli

Another book on power I would say is contrarian to my noble list of wholesome recommendations. Again, know evil and know good. This is a widely read book and elucidates much on power. It’s in my Defense Against the Dark Arts curriculum with 48 Laws of Power and The Dictator’s Handbook.

Crime and Punishment by Fyodor Dostoevsky

It discusses morality, leadership theory, pride, redemption, and isolation. It is important to understand where we came from to get where we are now. It discusses the “Extraordinary Man” theory of leadership, which, until the 20th century, is the leading leadership theory we have.

Steve Jobs by Walter Isaacson

Apple is a company worth studying to know mindset, creativity, and impact. Almost all the leadership and management lessons we need to learn to be successful are echoed and alluded to in this book. Steve Jobs is a leader worth studying, and the Isaacson biography is a masterpiece.

Crucial Conversations by Joseph Grenny

Have trouble with hard conversations at work? I found your next read! This is the survival guide for the sticky talks. If you’re not comfortable with conflict and emotion, Crucial Conversations is a great read. I would say I am conflict positive, and this book is an awesome field guide reminder for how best to approach the tough stuff.

The Dictator’s Handbook by Bruce Bueno de Mesquita and Alastair Smith

Core curriculum for my Defense Against the Dark Arts class. Want to understand politics and modern power control? Here you go! The new Netflix series How to Become a Tyrant is partly based on this book.

General Recommendations

What Color Is Your Parachute? by Richard N. Bolles

If you are looking for a job or suspect you will be soon, this is THE job search book. I have nothing but positive thoughts and recommendations for this book for the professionally lost and the job seekers out there.

Norwegian Wood by Lars Mytting

A few years back, I got a wood stove and started to cut and stack my own wood in preparation for the winter. It has changed my mindset around my home, my chores, and energy systems in general. I believe this book is a great book for those chasing self-mastery and self-development. Wood is all about preparation, perfection in the repetition of tasks, learning about trees, and a fuel source that has been powering humanity for almost all of our existence.

The Brothers Karamazov by Fyodor Dostoevsky

Leadership is about setting an example. The Brothers Karamazov is a life-changing piece on what it means to be a human.

Podcasts

Huberman Lab

New to science and scientific literature? This is an extremely digestible way to get involved in science. Managers and leaders need to be making fact-based decisions. This is a great way to get exposed to science in a fun way. There are great episodes on hydration, depression, addiction, and so on; they all teach us about being human.

Dare to Lead by Brené Brown

My favorite episode is one she did years ago with Simon Sinek. They talk about the “long game” mindset and how it changes our decisions and mindset at work.

This American Life

Growing up, this podcast taught me about what it means to be an American and about life. Learn about other people and build empathy. If you feel your horizons are shallow, haha, this is an awesome podcast for you to listen to.

The Moth

Another empathy builder with stories about the human experience. There’s something healing and educational about listening to the stories of other people. Check this one out as the perfect commute companion.

The MartyrMade Podcast: “Fear and Loathing in New Jerusalem” and “The Complete Jeffrey Epstein”

History classes did us all dirty by not teaching us about the history of the Middle East. If you don’t know the major beats of the Israel-Palestine conflict, you need to spend the time learning. The Jeffrey Epstein podcast episode by MartyrMade is the core curriculum in my Defense Against the Dark Arts class. Does it make me lose my appetite? Yes. Is it important to know? Also yes. We need to shine a light on the dark areas of society in order to clean out the cobwebs.

Arnold’s Pump Club

Short, under five minutes, regular, and positive. Arnold is a huge role model of mine in what it means to be a man. Especially as he has aged, check this out for some positivity.

Shows

Ted Lasso

None of us will ever be Ted, but if we take elements from his example in the show and implement them at work, we can get the same positive effects in our teams. Ted Lasso is an awesome example of what it means to be a people-first leader.

One Piece

Yep, I have a 1300+ episode anime on my required reading list. The lessons in leadership are clear in One Piece. It is the most-watched TV show of this century, and I’d wager it will be the next. It’s a strong political commentary on global politics. The Straw Hat Jolly Roger is being used all over the world in rallies and protests against corruption and injustice. Find a way to engage in One Piece if you want to laugh, cry, and learn what it means to stand up for what’s right.

The most important step is the next one.

Dan

Be a part of the solution at www.Kestryledge.com

References

  • Sinek, Simon. Start with Why: How Great Leaders Inspire Everyone to Take Action. New York: Portfolio, 2009.

Willink, Jocko, and Leif Babin. Extreme Ownership: How U.S. Navy SEALs Lead and Win. New York: St. Martin’s Press, 2015.