The best books for leaders scaling themselves to scale their business

Lyssa Adkins Author Of Lead Together: The Bold, Brave, Intentional Path to Scaling Your Business
By Lyssa Adkins

Who am I?

For over a decade I helped people develop their skills and expand their leaderful-ness in Agile Coaching and I kept hearing the same blocker: “This is great and all, but my leaders don’t get it. They are the impediment.” After working with many thousands of Agilists I decided to go into the “belly of the beast” and personally coach leadership teams. What I found were not beasts or even garden variety egomaniacs. Instead, I found well-meaning people who are genuinely confounded by the complexity of today’s business landscape and who struggle with performance-killing team dynamics. Good news: the human technology to “solve” these issues is widely available. We know how.

I narrated...

Lead Together: The Bold, Brave, Intentional Path to Scaling Your Business

By Brent Lowe, Susan Basterfield, Travis Marsh

Book cover of Lead Together: The Bold, Brave, Intentional Path to Scaling Your Business

What is the book about?

Lead Together, authors Brent Lowe, Susan Basterfield, and Travis Marsh offer founders, CEOs, and other leaders a radical new way of working and scaling a business. The audiobook is narrated by Lyssa Adkins, an internationally recognized thought leader in Agile, a coach and guide to leadership teams, and a leader herself.

Shepherd is reader supported. When you buy books, we may earn an affiliate commission

The books I picked & why

Book cover of Scaling Leadership: Building Organizational Capability and Capacity to Create Outcomes That Matter Most

Why did I love this book?

This book posits that the most important function of an organizational leader is to create other leaders throughout the organization. That’s right…not problem-solving, not clever strategy, not vision but leadership development. That’s because those other aspects are “table stakes” for the game of leadership in today’s complex business world. What I like about this book is that it is based on a huge pool of data about what makes leaders effective in the 21st-century and many of the insights are drawn from leaders themselves….from the feedback they give when they evaluate other leaders using the Leadership Circle Profile 360° assessment. It’s a nice marriage of relatable info “from the horse’s mouth” and decades of leadership theory borne out by insights from the assessment of hundreds of thousands of leaders. If you want to very specifically know what it takes to be a 21st-century leader, this book is a great place to start.

By Robert J. Anderson, William A. Adams,

Why should I read it?

1 author picked Scaling Leadership as one of their favorite books, and they share why you should read it.

What is this book about?

Transform Your Organization by Scaling Leadership

How do senior leaders, in their own words, describe the most effective leaders-the ones that get results, grow the business, enhance the culture and leave in their wake a trail of other really effective leaders? Conversely, how do senior leaders describe the kind of leader that undercuts the organization's capacity and capability to create its future? This book, based on groundbreaking research, shows how senior leaders describe and develop leadership that works, that does not, that scales, and that limits scale.

Is your leadership built for scale as you advance in today's volatile, uncertain,…

Book cover of Evolvagility: Growing an Agile Leadership Culture from the Inside Out

Why did I love this book?

This book gives the philosophical underpinning for why creating a leadership development culture in all parts of your organization is essential for working in our VUCA (volatile, uncertain, complex, ambiguous) business landscape. And, it shows you how to do it with specific practices and new-mindset concepts. It is geared toward organizations with Agile ways of working in the environment, but is also useful if Agile is not present. I especially enjoy the way several theories of adult development are interwoven in this book which makes using them to guide leadership development strategies (your own and others) simpler and more immediately applicable.

By Michael Hamman,

Why should I read it?

1 author picked Evolvagility as one of their favorite books, and they share why you should read it.

What is this book about?

Organizations around the globe are struggling to adapt to an increasingly complex and turbulent social, economic, technological, and business environment—whether they be banks, product development companies, or city councils. Many are responding by embracing agility as a way of working—some with a primary orientation around operational agility (Agile software development methods such as Scrum and SAFe), others focusing on customer development agility (e.g., Lean Startup), while others are embracing a broader business agility. In almost all of these cases, the prevailing notion of agility is concerned primarily with processes and practices, with systems and structures—a form of outer agility. But,…

Book cover of Systems Inspired Leadership: How to Tap Collective Wisdom to Navigate Change, Enhance Agility, and Foster Collaboration

Why did I love this book?

This one is hot off the presses in 2021. It gathers the powerful principles and processes from Organization and Relationship Systems Coaching and packages them for leaders. It “ups the ante” by showing how a systems-inspired orientation is critical for leaders to take, and why, and how to do it. I especially like that a big portion of the book is meant to be your just-in-time resource when you need to bring forth a specific leadership competency so that you can increase the relationship systems intelligence of the system and lead to much better outcomes. You can just flip to that specific competency and get the juice you need.

By Frank Uit de Weerd, Marita Fridjhon,

Why should I read it?

1 author picked Systems Inspired Leadership as one of their favorite books, and they share why you should read it.

What is this book about?

Today’s 21st Century leaders face tremendous pressure in an increasingly complex and fast-changing world, where traditional leadership models have become obsolete. To transform and transcend these challenges a new type of leadership is essential.


Systems Inspired Leadership (SIL): a powerful alternative for innovative leaders. Instead of an outmoded and ineffective top-down, leader-knows-all style that results in stress, pressure, and anxiety, SIL offers a fresh, proven approach for achieving optimal results for your organization.

This approach helps to overcome barriers and open doors to growth and innovation by tapping the collective wisdom of the organization. Instead of trying to…

Book cover of Leadership and Self-Deception: Getting Out of the Box

Why did I love this book?

This book will give you a much-needed “kick in the keister” as my grandfather would say. It helps you identify the specific way that you are “in the box” of distorted thinking and blaming other people (or yourself) when things don’t go according to plan. This book won’t leave you in the box, though, it offers ways out so that you can start to see your part in the “people problems” around you and change those dynamics completely. You can read this one like fiction because it’s told in a business fable style. I found that made it a delightful read and easier to receive challenging messages. 

By Arbinger Institute,

Why should I read it?

3 authors picked Leadership and Self-Deception as one of their favorite books, and they share why you should read it.

What is this book about?

This third edition of an international bestseller--over 2 million copies sold worldwide and translated into 33 languages--details how its powerful insights on motivation, conflict, and collaboration can benefit organizations as well as individuals.

Since its original publication in 2000, Leadership and Self-Deception has become an international word-of-mouth phenomenon. Rather than tapering off, it sells more copies every year. The book's central insight--that the key to leadership lies not in what we do but in who we are--has proven to have powerful implications not only for organizational leadership but in readers' personal lives as well. 

Leadership and Self-Deception uses an entertaining…


By Margaret J. Wheatley,

Book cover of Perseverance

Why did I love this book?

Amazon tells me I have bought this book 8 times. Honestly, I’m surprised it’s that few. I tend to give Perseverance to colleagues and leaders I am coaching. We all need a little help “keepin' on keepin’ on” when we are doing the heavy lifting of inner development and this little book does that. Perseverance manages to be simple and profound, short and deep, and oh, so helpful for functioning in the midst of chaos. You can open it to any “random” page and get the message you need in the moment, or to prepare your mind and heart for the day ahead. Given the permanent whitewater we leaders find ourselves in, the need for this kind of inner resourcefulness is essential, and the need to replenish it constantly.

By Margaret J. Wheatley,

Why should I read it?

1 author picked Perseverance as one of their favorite books, and they share why you should read it.

What is this book about?

In this inspiring and beautifully illustrated book, bestselling author Margaret Wheatley offers guidance to people everywhere for how to persevere through challenges in their personal lives, with their families, at their workplaces, in their communities, and in their struggles to make a better world. She provides hope, wisdom, and perspective for learning the discipline of perseverance.

Wheatley does not offer the usual feel-good, rah-rah messages. Instead, she focuses on the situations, feelings, and challenges that can, over time, cause us to lose heart or lose our way. Perseverance is a day-by-day decision not to give up. We have to notice…

5 book lists we think you will like!

Interested in leadership, perseverance, and success in life?

9,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about leadership, perseverance, and success in life.

Leadership Explore 322 books about leadership
Perseverance Explore 13 books about perseverance
Success In Life Explore 205 books about success in life

And, 3 books we think you will enjoy!

We think you will like The Leader on the Couch, Maslow on Management, and Man’s Search for Meaning if you like this list.