A bunch of professional development books on a shelf

The New Leader’s Bookshelf

It will come as no surprise to anyone that knows me that books have played an incredibly important role in my leadership growth. The only thing that I can think of that has had as much an impact has been finding opportunities to be on both sides of mentorships, but books have been the most consistent throughline on my journey. <shameless plug> If you’re so inclined, you can listen to Dawn and I talk about leadership books, even.</shameless plug>

Even as much as I love books and learning, I freely confess that “self help” books—especially those devoted to professional development or leadership skills—are a mixed bag, and that mixture is not weighted toward quality. The field is rife with trite, repackaged ideas; facile derivations of more established works (do we need more Zen and the Art of Leadership or The Art of War for Managers?); incredibly vague pap; or dangerously misguided approaches. However, there are gems out there.

It was while sifting through some of that morass to recommend such gems to a colleague that I had an idea: putting together a “bookshelf” of sorts for the new leader. My goals are simple: a manageable number of books that would guide a leader from “I am pretty sure I want to lead” through “oh shit, I have a team now what” without being overwhelming or excessively jargon-y or attempting to be overtly clever—oh, and without breaking the bank.

This is the result. A dozen books that divided themselves naturally into three discrete phases of becoming a leader that, if you bought them all at once, would set you back roughly $200. The intention is that these books can be read in order at a comfortable pace—usually around one every month or two—and that their lessons can be put into practice by leaders and aspiring leaders alike.

I’m Going to Be a Leader.

The degree of investment in leadership here is low; so, too, is the investment that should be needed to start laying a foundation. These books focus on introducing a mindset that is almost assuredly new to a prospective leader. The goal here is to challenge some preconceptions, introduce some important ideas, and to give some tangible strategies that can be leveraged to get immediate wins. This group should help smooth the transition from considering leadership as a possibility through the first few months as a new leader of people.

The Little Guide to Empathetic Technical Leadership by Alex Harms

This is the first of two books I hand every leader I mentor or lead. I don’t think that it is even slightly an exaggeration to say that it radically changed my approach; both to leadership and to being a member of a team alike. Very much focused on aspects of leadership that are not often top-of-mind for a new leader, for many readers this will be an introduction to collaborative leadership, supportive coaching, and intentional environment building. Equally importantly, it’s a first introduction to many of the importance of building an environment that encourages and nurtures diversity. If you don’t read any of the rest of the books on this list, read this one.

If you’re interested in our bookclub review of the book, here it is!

The Art of Leadership: Small Things, Done Well by Michael Lopp

This is the second of the two books I hand to leaders. These are best read as a one-two punch of philosophy and application. Lopp’s book is broken into three sections—one each for managers, directors, and executives—and within each section lays out practical skills and scenarios that leaders can learn and apply. Heavier on tactics than strategy, this is a great read to start thinking about how to apply leadership skills.

If you’re interested in our bookclub review of the book, here it is!

Slack: Getting Past Burnout, Busywork, and the Myth of Total Efficiency by Tom DeMarco

The real goal I have in mind when I recommend Slack to people is to break through a preconceived notion that folks have about efficiency and effectiveness in human beings. In a scant 250 pages, DeMarco makes a compelling case for making “slow down to speed up” a matter of practical necessity rather than something nice to see on a motivational poster.

If you’re interested in our bookclub review of the book, here it is!

The Five Dysfunctions of a Team: A Leadership Fable by Patrick Lencioni

The last book for beginners uses a fictional narrative to tell a story about the archetypes commonly found on teams, the impact they have, and some mechanisms for managing that impact. The highlight of this book, for me, is that it is one of the rare books to give a realistic perspective of both halves of “coach up or coach out.”

If you’re interested in our bookclub review of the book, here it is!

Oh Shit, I’m a Leader!

Having mentally cleared the way for new ideas and invested fully in the notion that great leadership is going to require great change, it’s time to lay a philosophical foundation for leading humans. This foundation goes beyond personal preference and lays the groundwork for adapting leadership tactics to one’s style. Extending new leaders beyond the initial, formative phase, this group takes the new leader through that important first year to year-and-a-half of leadership.

Start with Why: How Great Leaders Inspire Everyone to Take Action by Simon Sinek

The trickiest bit of starting to lead a team is understanding how to get people to know what to do and how to do it. Start with Why does an admirable job of describing a why-based, influence-driven leadership approach.

If you’re interested in our bookclub review of the book, here it is!

Drive: The Surprising Truth About What Motivates Us by Daniel Pink

One of the core leadership skills that those new to the trade find elusive is that of motivating people to do things in a positive, non-authoritarian way. Pink outlines the science and psychology behind motivation in a clear, engaging, and meaningful way.

If you’re interested in our bookclub review of the book, here it is!

Radical Candor: Be a Kickass Boss Without Losing Your Humanity by Kim Scott

Chief among the challenges for a new leader is developing a relationship that allows for praise and critique to both be equally appreciated. The stripped-down approach that Scott describes is easy to remember and easy to apply. A great primer with sufficient complexity to be great to return to as growth happens.

If you’re interested in our bookclub review of the book, here it is!

Tribes: We Need You to Lead Us by Seth Godin

This is a very short read that neatly pulls together some of the more involved lessons in the prior three books and does a great job of assembling them in something of a blueprint for leadership strategy. Understanding how a monoculture can inhibit a team’s success and how a diverse tribe can foster innovation is among the more powerful lessons of the book. More importantly, if you’ve read this book and are not fired up to truly lead your team to greatness, I can only assume you have no soul!

Okay, Now What?

Now that the team has been formed and some important foundational elements have been put into place, it’s time to shift attention toward the crafting of a unified, cohesive team. The path to “high performing” teams—or Tuckman’s “Performing” level—requires understanding different types of people and learning to engage on a wide variety of levels and from a broad spectrum of perspectives. This group introduces new points of view and approaches to take a new leader through the end of their second year of leadership.

Talking to Strangers: What We Should Know About the People We Don’t by Malcolm Gladwell

This is not a book about leadership. It is also not especially a book about self improvement. What it is is a brilliant treatise on interacting with people that we don’t know or whose perspectives are foreign to us. There are few skills more important to becoming a leader than to be able to understand mindsets that differ from your own. This is a challenging read because it covers intensely uncomfortable—albeit very important—subject matter, but I’ve encountered few books that better set up the mindset and the conversations that have to take place in order to build a strong, diverse team.

If you’re interested in our bookclub review of the book, here it is!

Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration by Ed Catmull

Ed Catmull does a brilliant job of describing how to work alongside a visionary like Steve Jobs, but also manages to lay out a blueprint for how to create, convey, and collaborate toward a shared vision with a high performing team full of motivated and talented people—an essential set of skills for turning a group of people into a high performing team.

If you’re interested in our bookclub review of the book, here it is!

The Mentor Leader: Secrets to Building People and Teams that Win Constantly by Tony Dungy

An NFL coach that brought a team from bottom of the league to playoff contenders and, ultimately, Super Bowl winners must know something about putting together cohesive teams. Dungy describes his approach in clear, actionable language that will help leaders elevate their teams from reliable to outstanding. I’m not a sports enthusiast, but I found the stories and comparisons engaging and illustrative throughout.

The Mythical Man-Month: Essays on Software Engineering by Frederick P. Brooks Jr.

The final book on the bookshelf is in that position because of the danger that it presents. This collection of essays is older than I am, and there are elements of this book that show its age, but the fundamentals gained through the previous 11 books will enable readers to understand and absorb the timeless and broadly accurate lessons within. Some aspects have aged poorly (I had forgotten that it introduces the idea of a 10x programmer), but the concepts are sound and beautifully conveyed—an excellent capstone for the new leader.

Summary

And there you have it. Twelve books encompassing some 3,300 pages to help guide the way through the first two years of stewardship over the lives and careers of others. You can find this list on over on Amazon here or on Goodreads here to help you get started on your leadership journey or for you to provide to someone you know that’s starting a journey of their own. In either case, good luck!