Books on leadership abound, but several I’ve read over the years felt formulaic and lacking in creativity. The books featured here give a fresh take on many traditional concepts and introduce novel ideas wrapped in engaging stories.
While this list represents a range of styles, all of the works share common threads urging readers to lead with honesty and integrity, think deeply about organizational values, and learn from inspirational leaders who have broken out of the mold. I’ve listed the books in the order of how much I enjoyed reading them, starting with my favorites.
1. Shoe Dog: A Memoir by the Creator of Nike
Ratings: 4.48 Goodreads / 4.8 Amazon
The likelihood that most of us will found a Fortune 500 company is slim, but Phil Knight has some insights that apply to pretty much anyone—and his story is entertaining to boot. Shoe Dog is a rich tale of the origins of Nike, which started with Knight’s unrelenting dream and a whole lot of hustle.
Knight’s journey had humble beginnings in Oregon, but he takes us all over the globe. Fresh out of business school in his mid-twenties, Knight made his way to Japan, the running shoe mecca of the 1960s. He returned home with a small sample of Onitsuka Tigers—which he sold from the trunk of his car—and from there, he was off to the races. By way of the vivid play-by-play recounting of his adventures, Knight takes us through his process of self-discovery and teaches us how his steadfast belief in a dream and a mission was so successful at drawing other people in, ultimately forming the giant we know today as Nike.
Knight gives an inside look at what it’s like to live and breathe your business. He was obsessive about building his company, and he is honest about the ways in which that obsession impacted his family life and, at times, his own mental health. Just reading about his burnout was enough to leave me feeling depleted. But to Knight, work was never “just business”—he saw it as a higher calling. With this mindset, Knight believes, “the fatigue will be easier to bear, the disappointments will be fuel, the highs will be like nothing you’ve ever felt.”
Shoe Dog delivers a well-crafted reflection on one of the most iconic companies of our time and would make a great first read of 2021.
2. Dare to Lead: Daring Greatly and Rising Strong at Work
Ratings: 4.15 Goodreads / 4.7 Amazon
If you haven’t read any of Brené Brown’s books, this is a good place to start, as she covers a lot of ground from her previous works. I, however, happen to be a big Brené fan girl—so I didn’t mind the repetition of her prior themes, which center on her life’s work of defining vulnerability and shame, with a particular focus on the ways shame holds us hostage in our lives, relationships, and careers.
In her introduction, Brown outlines her goal for the book: imparting to the reader everything she’s learned in her two decades of research and her work with hundreds of organizations. She also wanted readers to be able to consume the whole book in the time it takes to fly from NYC to LA—not that we are traveling much these days. I didn’t finish it quite that quickly, but I read it pretty methodically and was able to complete it in a single weekend.
Dare to Lead begins by acknowledging the pressing need for more brave leaders and more courageous cultures. Brown’s team surveyed senior leaders who identified behaviors and issues that often stand in the way of building trust and courage in the workplace—including avoiding tough conversations, being defined by failures, and neglecting to operationalize organizational values. Brown breaks down why we often default to these problematic behaviors, and how brave leaders can begin to shift their cultures to increase self-awareness and courage, thus creating environments in which people thrive.
One of my favorite takeaways—and one that Brown repeats a few times throughout the course of the book—is the phrase, “Clear is kind. Unclear is unkind.” Brown notes the unfairness of blaming a colleague for not delivering on a project, when the expectations were never clear in the first place. To help establish clarity, her team adopted the phrase, “What does ‘done’ look like?” They asked this question as a precursor to each project to ensure everyone carried out their tasks with shared understanding. I, for one, can think of many scenarios when these five little words would have saved me a lot of headaches over the years.
Another tidbit I found valuable was a rule Brown shared about her own company. In her organization, no one is allowed to criticize a point without offering another point of view in return—no tearing down without suggesting how to build it better.
Dare to Lead is chock full of valuable advice for leaders, but I’d argue it’s a beneficial read for anyone looking to improve their relationships in work and life in general.
3. Permission to Screw Up: How I Learned to Lead by Doing (Almost) Everything Wrong
Ratings: 4.27 Goodreads / 4.8 Amazon
Much like Shoe Dog, Permission to Screw Up delivers advice in the format of an engaging story. I found it to be a quick and enjoyable read.
The story begins with author and small business owner Kristen Hadeed finding herself in a prickly predicament, with 75% of her employees threatening mutiny in the midst of a massive contracted job—a scene that would have ended her budding company if she failed to turn it around. Luckily for her readers, that was the moment that inspired her to become a better leader—and to leave some notes for us to learn from.
As you can likely deduce from the title, Hadeed’s central argument is that mistakes can be our greatest lessons—and rather than trying to avoid them at all costs, we should expect them to happen, allow room for people to screw up, and give those folks a chance to fix their flubs and learn from them.
I didn’t stumble upon anything particularly groundbreaking in Permission to Screw Up, but I did find that Hadeed was able to bring important concepts to life through her honest storytelling. I enjoyed watching her unfold into a strong, mature leader over the course of the book. In the early years, she tried to connect with her employees (many of them around her same age) by throwing parties, but she wisely traded in keg stands for intentional one-on-one time with employees outside of the office. These real, meaningful connections increased mutual trust and fostered a culture with genuine camaraderie and loyalty. Hadeed believed so strongly in the value of building relationships that she began to pay employees to hang out for fifteen minutes before and after their shifts at the office. She considered it money well spent for the trade-off of encouraging close bonds among her team members.
Hadeed essentially takes you on her journey of discovering what meaningful leadership looks like. She has good advice for new leaders, stressing the value of getting honest feedback from employees and the importance of making sure those who work for you know that they are trusted and valued. But most refreshingly, she gives us all a license to screw up.
4. Wooden on Leadership
Ratings: 4.39 Goodreads / 4.8 Amazon
Coach John Wooden was a successful leader by any definition, but his perspective on success was different than that of most other coaches, athletes, and fans. For a man who won many championships, it is surprising that he seldom—if ever—mentioned the goal of “winning” when speaking to his players. Wooden’s idea of success, which plays heavily throughout his book, is helping others achieve greatness.
Wooden’s ideas are a lifeline for those of us who suffer from imposter syndrome. He makes a special effort to note that he never saw himself as a “natural-born leader.” Instead, believing that leadership is a learned skill, Wooden found that taking a systematic approach enabled him to excel. With concrete goals—and steps to achieve each one—Wooden makes becoming a good leader very accessible to anyone willing to put in the time.
Wooden’s stories will have large appeal to athletes and sports fans, but they are highly relatable to anyone who considers themselves part of an organization or team. He places a big emphasis on sharing success as teammates, evidenced by one of his more well-known sayings: “It takes ten hands to score a basket.” Wooden details many valuable examples of how to foster effective teamwork and maintain a culture of kindness and respect. According to Wooden, effective leaders are good teachers first—and they are always learning. Wooden on Leadership provides some excellent material from which to learn and share with others.
5. Wolfpack: How to Come Together, Unleash our Power, and Change the Game
Ratings: 4.08 Goodreads / 4.7 Amazon
United States Women’s National Team legend Abby Wambach is no stranger to leadership. The soccer star is a two-time Olympic gold medalist, the world record holder for most goals scored internationally (for both men and women), and the co-captain of the 2015 Women’s World Cup Championship team. In her brief book, Wambach lays out her playbook for disrupting the status quo and building a more beautiful world—succinctly described as “8 New Rules” that will change the game. And I’m not kidding about the succinct part—I read Wolfpack in just under an hour.
Wambach makes clear in her introduction that while this book focuses a great deal on women in leadership, the principles apply to people of all genders. She describes the way soccer shaped her identity for a long time, and how finding her place in the world outside of professional sports was initially a challenge. I enjoyed digesting the new rules Wambach lays out in Wolfpack, and I found them to be great starting points from which to brainstorm. My favorite: “Lead from the bench.” In this part of the book, Wambach describes dealing with the emotions of being her team’s co-captain in her final World Cup—but not being chosen as a starting player. She describes the heart and soul she poured into her teammates from the bench, to such an exhausting degree that she felt like she was out there playing with them. She models a different kind of humble leadership—one that we aren’t accustomed to reading about, but that is vital nonetheless.
I did find myself wanting more substance from the book, wishing Wambach had fleshed out her great ideas a bit more. Prior to reading the book, I listened to a podcast interview Wambach did with Brené Brown, which covered the majority of the book’s themes. If you’re on the fence about reading it, you may want to check out that conversation first.
6. Start with Why
Ratings: 4.08 Goodreads / 4.6 Amazon
After enjoying Simon Sinek’s immensely popular TED talk, I was eager to dive into his book. Sinek’s main premise is that truly inspirational companies and leaders set themselves apart from the rest by “starting with why.” He stresses the importance of leaders understanding their purpose or calling—and making that the focal point of their messaging and marketing, rather than simply extolling the value of the various products or services they sell.
Although I enjoyed the book—especially the numerous real-life examples Sinek provides to illustrate his points—I did find it to be repetitive at times. Additionally, most of Sinek’s key concepts are covered in his TED talk. But, if you watch the talk and find yourself wanting more, give Start with Why a shot!
The events of the past year have left many of us feeling drained and desperate for a sense of control. Sometimes, the best way to regain some perspective and hope—or even just get a moment to recharge—is to dig into a good book. Hopefully this list provides some ideas to start with. Enjoy!
