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  • Writer's pictureRobyn L Garrett

The Best Leadership Books for Every Age

“Learning is not attained by chance, it must be sought for with ardor and attended to with diligence.”

– Abigail Adams

Good leaders know that their journey is never done. A pastry chef might master the craft of making perfect mille feuille, but when it comes to leading people, perfection is a concept that might not even be worth talking about. That’s because we’re human — all of us. We don’t have a perfect recipe.

The good news is that we are not the first to attempt this endeavor. Many wise leaders have come before us and left us with guidebooks and kernels of wisdom so that we may adapt their techniques into our own lives.

Kids: Laying a Foundation

That’s right, we’re starting at the very beginning! I originally planned to save kids and teens for the “bonus round.” But as I compiled this list, I noticed just how much of it was about servant leadership. And what more important responsibility could there be than laying a strong foundation for the generations to come? Here are three great leadership books for the children in your lives:

1. The Giving Tree by Shel Silverstein

Ironically, I’m going to start this list with the book I hate the most (maybe that’s how you know it’s good, like a workout). If you haven’t read this in a while, I recommend really steeling yourself for the intensity of this short journey. Giving is hard — brutal, even. For parents and, I would argue, leaders, it never ends. This is a great way to foster young hearts of gratitude. Find it on Amazon.

2. Princesses Save the World by Savannah Guthrie

If you aren’t ready for something quite so emotional, you might want to skip directly to Savannah Guthrie’s Princesses Save the World. This book is the followup to Princesses Wear Pants, but its themes of teamwork, problem solving, and social responsibility help it stand out above other children’s stories. I guarantee that both both boys and girls will love this one and come out feeling more powerful than they did before. Find it on Amazon.

3. Oh, the Thinks You Can Think! by Dr. Seuss

One of AIIR's board members, digital innovation and transformation executive Dr. Michael Jabbour, recently presented to the AIIR team in our Learning & Shaping series. He told us “the time is soon coming when we will need more philosophers than coders.” This book is great for sparking creativity, effort, and optimism in young minds. Find it on Amazon.

Teens: Getting Ready to Lead

4. The Hard Thing About Hard Things by Ben Horowitz

I might be the only one to recommend this book for teenagers, but hear me out. In this book, Ben Horowitz tells his story of dealing with unexpected difficulties and handling situations when there is no perfect solution, and that is a lesson best learned early. One theme that I find when working with young leaders is that they think there is some sort of “secret solution” that they haven’t learned yet or that is being hidden from them to make life difficult. But (at least in my experience) that isn’t the case. It’s best to roll up your sleeves, put your thinking cap on, and deal with the situation at hand using the best information and resources possible. Each of these learning experiences leads to the next and, eventually, they build a great leader. Find it on Amazon.

5. The Happiness Project by Gretchen Rubin

We are putting more pressure on teens today than ever before. The world of overscheduled extracurriculars, traveling sports teams, and cutthroat college admissions applications is a tough one and, honestly, I doubt I could survive if I had to go through it today. Gretchen Rubin’s tome takes a different approach to thinking about your life — one that is driven by the question, “What makes me happy?” What better question could there be to ask before you borrow an average of $40K in student loans? Find it on Amazon.

6. What Color is Your Parachute by Richard N. Bolles

I remember a good friend of mine receiving this book as a graduation present from her father many years ago. It’s an act that I have gone on to repeat many times in the hopes of passing this wisdom on to new generations. While, back in my day, it was perfectly fine to spend your summers hocking movie tickets, today’s young adults are expected to go after brand-name internships and spearhead their own leadership projects. This book’s practical tips are perfect for those that are starting to get serious about professional opportunities. Find it on Amazon.

Your 20s: Embracing Humility

7. How to Win Friends and Influence People by Dale Carnegie 

Repeat this mantra: it’s not about me, it’s not about me, it’s not about me. Now that you’re entering the professional world, it’s time to start thinking (and talking) less about yourself and more about other people. Whether you choose the original version or the new “For the Digital Age” edition, this classic is full of practical tips on how to get out of your own way. Find it on Amazon.

 “The best minute I spend is the one I invest in people”

-Ken Blanchard

8. The New 1 Minute Manager and The 5 Minute Manager Meets the Monkey by Ken Blanchard and Spencer Johnson

These books are so valuable and such quick reads that I’m going to cheat and put them together here. In The 1 Minute Manager, Blanchard takes something that often seems so complicated and makes it simple: effective management should be done in the moment. I couldn’t agree more with the statement “The best minute I spend is the one I invest in people.” It will change your leadership style, if not your life. 

Getting introduced to the concept of “the monkey” early can help you avoid a lot of stress and worry about disappointing others. True servant leadership empowers others to solve their own problems and this book helps leaders of all ages understand how to do that better. Find them on Amazon.

9. How to Be a Great Boss by Gino Wickman and Réne Boer

Gino Wickman and the mentor that introduced me to his work changed my life. In addition to servant leadership, you may notice another key theme emerging here: great leaders understand that they can’t do it alone. The concept of Delegate and Elevate™ will change not just your team, but your organization. Never have I seen as much progress, creativity, and success as when this concept has been properly applied. Read this one again and again and never stop trying to live up to this high standard of leadership. Find it on Amazon.

Your 30s: Time to Get Serious

10. Good to Great by Jim Collins

Now we’re getting into the heavy-hitters. The audiobook for Good to Great is over 10 hours long and worth every minute. Collins’ research on why some companies make the leap and others don’t comes to the remarkable conclusion that discipline and a willingness to face the brutal facts are key paths to success. This rich text breaks down what it means to be a Level 5 Leader, how to find your Hedgehog Concept, and what it really takes to get the flywheel moving. Find it on Amazon.

11. The Advantage by Patrick Lencioni

The experience of reading Good to Great and The Advantage back-to-back is absolutely enlightening. Now that you’re getting into more organizational responsibility it is time to think beyond just you and your team. While he will be the first to tell you that the ideas in this book aren’t sexy, Lencioni does an amazing job of breaking down what it takes to create organizational health and stick to the principles that allow it to grow. This is the time to be open to vulnerability and look on the human side of what it takes to gain alignment among leaders. Once you’ve done that, you’re well on the way to creating powerful clarity in your organization. Find it on Amazon.

12. Explosive Growth by Cliff Lerner

At this point, you might be looking around at stories of startups that blew up overnight and dreaming about the day that might happen to you. In this book, Cliff Lerner tells the true behind-the-scenes story of how that happened to him and the many, many lessons he learned on the roller coaster ride that is entrepreneurship. What’s particularly great about this book is that Lerner references many other texts that benefited him in his leadership journey, admitting that there was a time he was reading a whole book every night. His 80 tips for explosive growth will spark plenty of creative ideas to take your organization out of the box and up to the next level. Find it on Amazon.

Your 40s: Challenging Everything

13. The Coaching Habit by Michael Bungay Stanier

Up until now we’ve focused on many techniques that will help you become a great leader, now it’s time to start transforming them into habits. Obviously, my unique experience working with top executive coaches from around the worldhas allowed me to see the incredible power of coaching across industries. Ever wonder how they unlock this incredible potential? Stanier’s 7 Questions will supercharge your servant leadership and get you saying less by asking more. Find it on Amazon.

14. Radical Candor by Kim Scott

Ah, one of my absolute favorites. If you haven’t seen Kim Scott’s TED Talk, stop what you’re doing and watch it now. Candor is one of the communication efforts that leaders often struggle with. But holding back won’t help your people grow and improve and it won’t get you out of any messes you might find yourself in. In this book, you can learn how to care personally and challenge directly in a way that works. Best of all, Scott reminds us that this isn’t just a style, it’s what your job as a leader is all about. Find it on Amazon.

15. What Got You Here Won’t Get You There by Marshall Goldsmith

I can’t tell you how often this comes up in executive coaching. By the time you reach this point in your career, you’ve learned techniques that really work for you. But then why are you still stuck? Well the world changes rapidly and we must change with it. Marshall Goldsmith, one of the most sought-after executive coaches in the world, is the master at helping leaders break free of the habits and assumptions that are holding them back. Find it on Amazon.

Your 50s: Rising to New Heights

16. Dare to Lead by Brené Brown

Everyone at the 2019 Annual SHRM conference this year was buzzing about Brené Brown’s keynote speech. This book is about bravery, vulnerability, and daring to recognize the potential in people and ideas. If you haven’t seen it already, I highly recommend her Netflix special. It’s a lovely introduction to her approach, filled with very human stories that remind us all that this work is hard but that we can do it if we have the right mindset. Her book goes further, delving into her research findings that there are four crucial skill sets that are 100 percent teachable, observable, and measurable. Find it on Amazon.

17. Executive Presence: What Nobody Ever Tells You About Getting Ahead by Sylvia Ann Hewlett

I once heard someone call this book the grown-up version of Girl, Wash Your Face. I’m not sure I’d put it like that, but it is certainly full of eye-opening insights that will help you bridge the gap between where you are and where you want to be. Combining this with What Got You Here Won’t Get You There is the perfect thought experiment that will allow you to break through by breaking down the things that are holding you back. Find it on Amazon.

18. Why Do So Many Incompetent Men Become Leaders? (And How to Fix It) by Tomas Chamorro-Premuzic

Whether it’s time for you to man up, woman up, or just step up in general, this book is a great read. AIIR Advisory Board member Tomas Chamorro-Premuzic looks at decades of research on how leaders get into their positions and what actually makes them successful. Surprisingly, some qualities, like charisma, may get someone promoted but may actually be counterproductive to the organization in the long run. This provocative book is both timely and practical. Not convinced? Start out with his TED Talk on Why We Should Be More SexistFind it on Amazon.

60s and Beyond: Paying it Forward

19. Think Big, Act Small: How America’s Best Performing Companies Keep the Start-up Spirit Alive by Jason Jennings

This is no time to rest on your laurels! As we all know, leadership requires constant adaptation and perseverance. In this book, Jason Jennings discusses 9 unique companies that stunningly increased revenues and profits by ten percent or more for ten consecutive years. What was their secret? They think big but act small. This startup-like atmosphere cultivates a culture of ownership and encourages everyone to get their hands dirty. Find it on Amazon.

20. Trillion Dollar Coach by Eric Schmidt, Jonathan Rosenberg, and Alan Eagle

Legendary coach Bill Campbell was instrumental in shaping several Silicon Valley companies and coached leaders like Steve Jobs, Larry Page, and Eric Schmidt along with dozens more. In doing so, he created well over a trillion dollars in market value. In this book, three leaders from Google, Eric Schmidt, Jonathan Rosenberg, and Alan Eagle recount their firsthand experiences with Campbell. He wasn’t someone that sought the spotlight but rather someone that believed that servant leadership was valuable for leaders at any level, including the very top. Find it on Amazon.

21. Leadership in Turbulent Times by Doris Kearns Goodwin

We’ll end on something a little different – a historical retrospective of presidents Abraham Lincoln, Theodore Roosevelt, Franklin D. Roosevelt, and Lyndon B. Johnson. Doris Kearns Goodwin weaves their gripping stories together, positing that it isn’t innate qualities or talents that make great leaders, but that it is how we respond to adversity. A timeless lesson to benefit us all. Find it on Amazon.

Bonus Round: The Extra Edge

Ding, ding, ding! Welcome overachievers! If, at any point in knocking these books off of your literary bucket list, you find yourself ahead of the curve, here are three books that will benefit you at any age:

22. Start with Why and Leaders Eat Last by Simon Sinek

Simon Sinek is well-known as the authority on millennials in the workplace but these books are excellent for anyone that wants to be a more motivational leader. Both of these servant leadership concepts are so guttural that once you know them you can’t help but think about them in your daily life. Find them on Amazon.

23. Off-Centered Leadership by Sam Calagione

This is a personal favorite written by Dogfish Head founder and fellow Muhlenberg Alum Sam Calagione. Dogfish had many years of explosive creativity that led to both successes and failures (beer-infused soup? Pickles? soap?!). In this book Sam talks about how he knew it was time to make some changes but still maintained a culture that his recruiter called “the most unique she’d ever seen.” Find it on Amazon.

24. Extreme Ownership: How U.S. Navy SEALs Lead and Win by Jocko Willink and Leif Babin

“Leaders must own everything in their world. There is no one else to blame.” That’s the mantra of this book from two Navy SEALs turned leadership consultants. I have heard many people describe this as an intense experience that shows you want a person is really capable of. And if there is one thing I hope you learn from all of these texts, it’s that there is no end to the leadership journey. No matter where you are, there’s always a little bit further to go. Find it on Amazon.

Happy reading!



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