Personal Development

The best leadership books chosen by Vistage members and Chairs

best leadership books pile

The key to great leadership is excellent communication. So, it is little wonder that the best leadership books are concise, engaging and easy to follow. From irreverent sendups of common failures to painstaking dissections of the human condition, the following leadership books offer actionable insights to help helm a company, or a leadership team, to success. Vistage CEO members and executive coaches have recommended many of these titles to their peers for deeper insights, strategies and inspiration to tote along the challenging and rewarding leadership journey.

Vistage Members: Join the Lead & Read Network, your space for connecting with fellow business leaders who are passionate about personal growth through reading, discovering new books, and participating in engaging conversations about the authors that have influenced their leadership journeys.


Dare to Lead: Brave Work. Tough Conversations. Whole Hearts by Brené Brown

Brené Brown has made a career of transforming vulnerability into strength for personal and professional success. “Dare to Lead” builds on that groundbreaking work with fresh, new insights and provides a roadmap for affecting change in organizations and in leadership styles. Vistage member Jesi Wang says, “I’m a huge Brené Brown fan,” and predicts others will be, too.

The First 90 Days: Updated and Expanded: Proven Strategies for Getting Up to Speed Faster and Smarter by Michael Watkins

The advice in this international bestseller is so sage, Vistage member Amir Shami said he read it twice. With a keen-eyed sense of workplace dynamics, Watkins provides strategies sharpened from his experience advising senior leaders in many types of organizations. He has seen firsthand the dangerous pitfalls inherent in leadership transitions as well as the proven framework for triumph.

The Infinite Game by Simon Sinek

In this riveting reflection of the game of life, Sinek provides a new language for business leaders to understand their role in their organizations and their organizations’ role in the world. Too many leaders think of business as a “finite game,” one with clear winners and losers. An “infinite game,” as defined by Sinek, is one in which the objective is to stay in the game while staying true to an organization’s just cause. Sinek provides a compelling argument against taking a short-sighted view of business, while providing a roadmap for courageous leaders to build organizations that endure.

Vistage Members: Watch for Simon Sinek’s discussion with Vistage CEO Sam Reese on the infinite mindset in January 2020! More information coming soon.

Traction: Get a Grip on Your Business by Gino Wickman

A recognized leader in building successful leadership teams, Gino Wickman lays out the six key components of growing and strengthening businesses. “Traction” provides the toolbox leadership teams can use to eliminate frustration and friction and create a company-wide culture of engagement in which all team members are dedicated to a company’s mission and success.

Radical Candor: Fully Revised & Updated Edition: Be a Kick-Ass Boss Without Losing Your Humanity by Kim Scott

“Radical Candor” has been a New York Times and Wall Street Journal bestseller for several years running. In this updated edition, Scott further hones her cultural touchstone concepts of honest feedback and professional development. Outlining specific steps, Scott encourages managers to challenge directly while communicating empathetically.

Vistage Member-Exclusive: See Kim Scott present “Radical Candor: Creating a Culture of Feedback” at the Vistage Women in Leadership event

Positive Intelligence: Why Only 20% of Teams and Individuals Achieve Their True Potential and How You Can Achieve Yours by Shirzad Chamine

With an enthusiasm that leaps off the page, Chamine’s New York Times bestseller espouses a groundbreaking set of exercises to help executives workout their “brain muscles,” increase their “positive intelligence” (PQ) score and access untapped mental resources.

The Gift of Struggle: Life-Changing Lessons About Leading by Bobby Herrera

“The best leaders are always learning,” Bobby Herrera writes. And from “The Gift of Struggle,” leaders can learn quite a bit. Revealing how he came to see his own difficult upbringing as a gift, Herrera provides the framework for putting life’s lessons into action. A gifted storyteller, Herrera’s work is as uplifting as it is thought-provoking. Each chapter ends with “Questions to Guide Your Journey,” challenging the reader to adjust their behavior to achieve desired outcomes for themselves, their company and the people they lead.

Turning the Flywheel: A Monograph to Accompany Good to Great
 by Jim Collins

Building off the success of his number-one bestseller “Good to Great,” Collins offers more takeaways about the importance of slowly gaining momentum – turning the flywheel – to reach a business breakthrough. Short on pages (only 44) but long on wisdom, Collins details how to build a flywheel by understanding the specific drivers of a business’s success. An invaluable accompaniment to “Good to Great,” and the ultimate how-to manual for any executive.

Leadership: In Turbulent Times by Doris Kearns Goodwin

After delving deep into the lives of Abraham Lincoln, Theodore Roosevelt, Franklin Roosevelt and Lyndon Johnson, historian Doris Kearns Goodwin emerges with a nuanced understanding of how great leaders overcome the challenges of their times. The result is boardroom wisdom forged in battle. An inspiring read for leaders during our own turbulent times.

Thinking in Bets: Making Smarter Decisions When You Don’t Have all the Facts by Annie Duke

A World Series of Poker gold bracelet winner and a National Science Foundation fellow in cognitive psychology, Annie Duke understands the difference between strategy and luck. Her illuminating book reveals that much of what we think we know about business strategy is – she’s willing to bet – wrong. With precise advice, Duke provides a plan for improving the way leaders collect and evaluate data to steer entrepreneurs toward well-informed results.

Scaling Up: How a Few Companies Make It … and Why the Rest Don’t by Verne Harnish

“Scaling Up” delivers actionable techniques so meaningful, it should be on every CEO’s nightstand. Vistage member Shannon Black, who has used Harnish’s tools to inform her own scaling efforts, describes the book as a “treasure trove,” saying, “I’ve never read a business book that is so lacking in filler.” Every page of the book is packed with high-value, exceedingly useable insights for running and growing a successful business.

Start with Story: The Entrepreneur’s Guide to Using Story to Grow Your Business By Lyn Graft

Rising above the noise doesn’t require a louder voice, just a more authentic one. Drawing from his own story and the stories he has elicited from entrepreneurs and business leaders in disparate industries, Graft provides precise, relatable advice to guide leaders toward finding and telling their stories. “Start with Story” underscores the power of emotional connections to inspire investors and draw customers.


Category: Personal Development

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About the Author: Vistage Staff

Vistage facilitates confidential peer advisory groups for CEOs and other senior leaders, focusing on solving challenges, accelerating growth and improving business performance. Over 45,000 high-caliber execu

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  1. Nancy Haboush

    November 5, 2020 at 3:44 pm

    GREAT list. I would add:
    The Four Agreements, Don Miguel Ruiz
    No Ego, Cy Wakeman
    The Speed of Trust, Stephen Covey
    First Break All the Rules, Marcus Buckingham
    Leaders Eat Last, Simon Sinek
    Start with Why, Simon Sinek
    Girl, Stop Apologizing, Rachel Hollis

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