12 Leadership Books I Recommend To Any Boss That Wants To Get Better
These days, a lot of leadership books are same-same-but-different. In the leadership category, it’s easy to be meh, but you can tell the authors that profoundly believe that their idea is different and might just re-shape someone’s life — it comes across in their writing.
In my opinion, what separates a good leadership book from a bad leadership book is conviction.
Here are a dozen leadership books that I find to be full of conviction, where the author has clearly gone (dare I say it) where others won’t to bring to life a unique idea that could be a genuine gamechanger.
1. Principles by Ray Dalio
Put simply: this book is so good that it makes Extreme Ownership, Radical Candor and every other transparency-focused leadership book seem derivitive. They’re not, of course, but if you dominate your sub-genre so comprehensively there’s no question your work moves straight into the must-read category.
The strength of Dalio’s belief system is that it’s experiential, data-informed, and isn’t merely self-serving for Dalio himself — in fact, his book makes no bones about the fact that he’s often the victim of his own principles.
Pay Attention To: Chapter 8, titled Hire Right, Becaue the Penalties for Hiring Wrong Are Huge, which is as close as you’ll get to a bible for recruitment philosophy.
2. The Best Team Wins by Adrian Gostick & Chester Elton
I didn’t expect much from this book, but the title roped me in and it went on to become the most-highlighted book on my Kindle. Packed with timely anecdotes, research, and nuanced opinion, I’m shocked this one hasn’t been a BIGGER hit.
Most striking is the depth with which Gostick and Elton dive into common management topics, yet arrive at vastly different conclusions to what you’ve heard in the mainstream commentary.
Pay Attention To: Chapter 1, titled Understand Generations. It slaps you in the face, and not in the Millennial-bashing way we’ve come to expect from many leadership thinkers.
3. Powerful by Patty McCord
I started reading Powerful at 11:30pm and before finishing the introduction I got out of bed, started up my laptop, and sent Patty an email. This is the book that calls bullshit on everything you thought corporate environments needed to be.
Like Dalio’s effort, the shrewdness in McCord’s book comes from the fact that she lived the entire thing and isn’t afraid to delve into the iterative nature of what transpired. Netflix made mistakes, McCord second guessed decisions, but for a tech company that was inventing the future, it was all a necessary and valuable part of the journey.
Pay Attention To: Chapter 2, titled Every Single Employee Should Understand the Business. It’s 13 uncomfortable pages that make you feel like you’ve been short-changing your employees this whole time.
4. Dare To Lead by Brené Brown
Brown is the global leader on courage, vulnerability, shame, and empathy, and Dare To Lead is the culmination of her seven-year study on the future of leadership. Like McCord, Brown’s writing style doesn’t pull any punches, but she’s magical in her ability to hold a mirror up to the reader and make you emotionally respond to her words.
Often, as you read, you’ll think “shit, she’s talking about me.”
Pay Attention To: The whole thing.
5. The Culture Code by Daniel Coyle
You’ll be hard pressed to find a must-read list that doesn’t include this book, and with good reason. The Culture Code is as close to as you can get to a Gladwellian novel that’s not written by Malcolm Gladwell. It’s one of those my-head-is-spinning-with-all-these-ideas kind of reads, and if you don’t start with a fresh highlighter you’re guaranteed to run out of fluorescent ink in no time at all.
I consider The Culture Code to be the book on how leaders create cultural systems that trigger learning, spark collaboration, build trust, and drive positive change.
Pay Attention To: Chapter 4, titled How to Build Belonging. It features a jaw-dropping portrait from inside the San Antonio Spurs, arguably pro sports’ most iconic culture.
6. Gridiron Genius by Mike Lombardi
Mike Lombardi has worked for three of the NFL’s Godfather-like figures: Al Davis, Bill Walsh and Bill Belichick. Hence, he knows a thing or two about how to build teams capable of sustained success.
In Gridiron Genius, Lombardi mixes historic stories with his own opinions, and recounts how some of football’s most well-known tales have, over time, grown legs of their own.
Pay Attention To: Chapter 3, titled In Search of Program Guys. It includes doozies like this one, which are true of not just sporting locker rooms, but corporate environments too: “You can’t bullshit an NFL locker room. Everybody on every team knows who the good players are, who the bad players are, and who the team’s favorite players are.”
7. The Captain Class by Sam Walker
What started as a simple idea for a Wall Street Journal essay has led Sam Walker down a path which now sees the journalist mentoring Chicago Bears quarterback Mitch Trubisky. Unable to find an unbiased, data-backed list of the best sports teams of all-time, Walker spent 11 years creating and refining his own formula — accidentally stumbling on a new leadership theory in the process.
The Captain Class rebutts many popular leadership fables and points out that each of the most dominant sports teams ever had a captain that displayed behavioral traits we wouldn’t ordinarily associate with leadership. This is an absorbing read.
Pay Attention To: Who’s not on the list (ie. most of the teams you think should be on there).
8. Leaders: Myth and Reality by Stanley McChrystal
Don’t take it from me, here is what Sheryl Sandberg wrote about this book:
“Leaders reexamines old notions of leadership — especially the outdated view that history is shaped by great men going it alone. General McChrystal shows us that leadership can take many forms, leaders often have different strengths, and great leaders can come from anywhere.”
And if you don’t believe Sheryl, you might believe Simon Sinek:
“Whenever Stanley McChrystal talks, I take notes. Leaders takes us deeper than most other leadership books into the true and often messy mechanics of leadership. Anyone who considers themselves a student of leadership must read this book.”
Pay Attention To: Section 3, titled The Founders, contains chapters that break down many pop culture misconceptions of Walt Disney, Coco Chanel, and the ego of entrepreneurial pursuits.
9. Sacred Hoops by Phil Jackson
Mindfulness and meditation were all the rage in 2018, but Jackson brought us mindful basketball in the early 90s and he was an enlightened cat as far back as the 70s.
When I recommend this book to people, I make sure to tell them that it’s not a basketball book, it’s an exploration of one man’s self-awareness, with a veneer of basketball applied over the top. While there are ample stories of figures you’ll recognize like Michael Jordan and Scottie Pippen, the book belongs in the spirituality section of the book store.
Pay Attention To: Chapter 7, titled Being Aware Is More Important than Being Smart, and Chapter 10, titled Coaching Michaelangelo (yes, this is an entire chapter on coaching Michael Jordan).
10. Build An A-Team by Whitney Johnson
If Where Others Won’t was looking for a date for the dance, it would ask Build An A-Team. Perennial bestselling author Whitney Johnson posits that learning is one of the core facets of a thriving corporate culture, and suggests strategies for how companies can realign their entire environment to foster growth in their employees.
With a sub-heading on nearly every page, this is one of those books you can pick up and open at any page and learn something new.
Pay Attention To: Chapter 3, titled Recruiting and Hiring. I highlighted 11 passages in this chapter alone. The sub-chapter called Hire Where Others Aren’t is an obvious favorite of mine.
11. 59 Lessons by Fergus Connolly
Connolly is a high-performance coach who has worked across the global sporting landscape, from the NFL to the AFL, GAA to EPL, there isn’t much he hasn’t seen. 59 Lessons is a collection of succinct ideas on leadership, culture and performance from the masters Fergus has worked with, and run into in his journey.
This is the best sports book for some time (you can trust me, I’ve read them all).
Pay Attention To: Lessons 7, 14, 17, 20, 26, 30, 34, 40, 46, 48, 51 and 56.
12. Leaders Eat Last by Simon Sinek
You just can’t have a leadership book list without Simon Sinek. And while Start With Why is Sinek’s seminal work, it is a book about communication. Leaders Eat Last is his first pure leadership effort and is also an instant classic.
Leaders Eat Last helped popularize the concept of psychological safety and, at least for me, was the first book to draw linkages to our chemical need to be a part of a collective, or ‘Circle of Safety’ as Sinek calls it. A wonderfully complete study of teams.
Pay Attention To: Chapter 1, titled Protection From Above. Johnny Bravo, what a hero!
If you want to talk about any of the books listed above, send me an email at email@example.com.
I hope my list helps.