Leaders Are Readers Collection 01: 5 Essential Books For New Leaders

“ A reader lives a thousand lives before they die.”

My late Grandfather gave me some advice when I was a young kid in awe of how he knew how to do anything from building his own house to MacGyvering a car part so my car ran longer. He told me that he learned all of it from books and that we could learn anything in the world if we applied ourselves. This was a man that walked the campus of Harvard almost every day and learned that wisdom lies in the people that came before us and know more than we do about topics. I took that advice and became a voracious reader. My personal goal is 2-books a week on average for 100-books a year, more during the pandemic. I read books on many topics - leadership, spirituality, meditation, boating, hockey, biographies, music, fitness, and more.

I wanted to share the books that have helped me along the way for a variety of applications, topics, times in my life, and other reasons. Some of these I keep on my bookshelf, some are on my kindle, some are tattered with notes and some I keep on my nightstand for constant reference. I hope you find it inspirational and find some gems you can add to your collection.

Leaders Are Readers Collection 01: 5 Essential Books For New Leaders

The journey of leadership never ends. And as we move through the ranks, the challenge of leadership changes with us. Becoming a new leader whether managing 1-person or 1,000 we can absolutely learn from those that came before us. Learn from their mistakes, their successes, their research and choose for ourselves, which to apply to our own path. These books are not one and done, they are references we can find solace in when faced with new challenges, feelings, or events in leadership. There is calm in knowing that leaders before you have felt what you are feeling, had the knots in their stomach that you have and that they do not know it all, regardless of how they portray their confidence. For new leaders, this opens up a world of possibilities. I hope you find some wisdom and inspiration from these selections.

  1. Reboot: Leadership And The Art Of Growing Up by Jerry Colonna

    Why This Selection?

    This book touched me deeply and I only recently read it in the past year or so. I connected with Jerry’s personal stories and how we must reconcile our demons from our youth that shape our feelings towards events, our reactions to situations and the recurring ghosts in our machine that show themselves at the wrong time. Everyone has ghosts in their machine and there is nothing to be ashamed of, recognizing them and working them out sooner rather than. later will make us better leaders. This book is for all leaders, but again, the sooner we can face the ghosts in the machine in our leadership journey, the better.

    His podcast is also amazing with live coaching sessions to learn from, it is a go-to for me on a weekly basis: The Reboot Podcast.

    Excerpts:

    “Radical self-inquiry is how we learn to become more of ourselves, more like ourselves, more authentic. More human. And better humans are better leaders.”

    “When we’re brave enough to admit our fears, uncertainties, and doubts, we open the gift box.”

    “We forge our truest identity by putting our heads into the mouths of the scariest demons, the realities of our lives. Only by facing our fears, our prejudices, our passions, can we transform the energy that is the source of our aggression, the source of our confusion, the source of our struggle.”

    “The frustrations that drove the company to try to change and innovate get banished.

  2. The Courageous Follower: Stand Up To And For Our Leaders by Ira Chaleef

    Why This Selection?

    I found this book a while back on my leadership journey. It’s a mind-bender to think that to be a better leader you have to be a better follower. But, it makes total sense in many regards. Everyone has a boss, whether the board of directors or the buyer of your product/service. Every leader is in the service of a leader. And one of my favorite quotes, “Even leaders need leaders.” I have worked for some amazing people and I’ve worked for some not so amazing people - in either regard, I pulled on the learning from this book to understand the follower/leader dynamic and through building a relationship, being honest and an advisor for those I’ve worked for and with. Not every person responded well to that relationship but as a leader, it gave me better empathy for those that were/are following me on their journey. Again, that relationship didn’t always click for a variety of reasons, nonetheless, this book never gets old and will have a long tail on your journey.

    Excerpts:

    “It is difficult to appreciate the external pressures on leaders until you have walked in their shoes until you have had to make payroll, bring a squadron through safely, or respond to the outraged constituents who elected you.”

    “We must understand the forces that chisel away at their creativity, good humor, and resolve. We must learn how to minimize these forces and create a climate in which a leader’s strengths are magnified, so a leader can better serve the common purpose...”

    “Courageous followership is built on the platform of a courageous relationship. The courage to be right, the courage to be wrong, the courage to be different from each other...”

    “Followers who are closest to a leader carry pivotal responsibility; they markedly shape the tone and outcomes of a leader’s tenure.”

  3. Rising To Power: The Journey Of Exceptional Executives by Ron Carucci and Eric Hansen

    Why This Selection?

    From the jacket: Nearly two-thirds of all leaders entering executive roles lack sufficient understanding of what is required of them and are unprepared for what they will face, which explains why 50 percent of them will fail in the first 18-months.

    This is a book I gave to all new executive leaders rising through our organization in the past 5-6 years. This book if read with an open and clear mind, will help the new leader avoid the massive pitfalls as the air gets thinner when moving through the leadership journey. Closer to the top of the pyramid, the air is thin and mistakes happen because of it - they call this altitude sickness. The game moves faster, the hitting is harder and the stakes are higher. I felt this as I moved through the ranks and watched other leaders gasp for air, as well. The authors leveraged an AI-driven research method with thousands of executives to present these findings.

    Excerpts:

    “You are likely terrified while having to look confident.”

    “Those who show up with answers and a toolbox of successful solutions from their past track record ready to deploy in my organization are likely to wreak havoc.”

    “Many start out declaring they will “rise above” these factors. That is until they actually face them. The discouraging and disorienting effect of political factors can result in insecurity, paranoia, and the endless second-guessing of self and others.”

    “Wing walking” is the act of moving across the surface of an airplane wing while the airplane is in flight, and it is an apt metaphor for the process of executive transitions.”

  4. Mastery by Robert Greene

    Why This Selection?

    This book is about keeping an apprentice mindset no matter where you are in your career or on your learning journey. But especially for new leaders, having an apprentice mindset is critical to mastering any topic or situation. Being open, present and aware of those that you are learning from. Mastery requires putting in the work, studying, making mistakes, honing your craft and paying it forward. Robert Greene is my personal favorite author for how he extracts epic learning from history and moments both in support of and counter to the law and theory presented.

    Excerpts:

    “Choose the mentor who best fits your needs and connects to your Life’s Task. Once you have internalized their knowledge, you must move on and never remain in their shadow.”

    “Understand: when you enter a new environment, your task is to learn and absorb as much as possible. For that purpose, you must try to revert to a childlike feeling of inferiority—the feeling that others know much more than you and that you are dependent upon them to learn and safely navigate your apprenticeship.”

    “The Apprenticeship Phase is more relevant and important than ever, and those who discount this notion will almost certainly be left behind.”

    “Your goal is always to surpass your mentors in mastery and brilliance.”

  5. Dare To Lead: Tough Conversations. Whole Hearts by Brene’ Brown

    Why This Selection?

    I love any book that combines spiritual principles with leadership theory. She does not get deep into spirituality and the core topic of this book is vulnerability as a leader. In many ways, this book also discusses deeply the follower/leader relationship - what a healthy relationship looks like from both angles and the attributes that send them off the rails. The concept of leadership has evolved considerably from the hierarchical pyramid with the all-knowing leader never showing cracks to more of a circular relationship with trust, vulnerability and productive behaviors.

    Excerpts:

    “Practicing self-compassion and having patience with ourselves is essential in this process.”

    “Developing the caring and connection or find a leader who’s a better fit. There’s no shame in this - we’ve all experienced the kind of disconnection that doesn’t get better despite our strongest efforts”

    “The physics of vulnerability: If we are brave enough often enough, we will fall. I’ve never met a brave person who hasn’t known disappointment, failure, or even heartbreak.”

    “Get clear on whose opinions of you matter.”

    “The people on your list should be the people who love you not despite your vulnerability and imperfections, but because of them.”