What to Read When: Book Suggestions from the Reboot Coaches

Executive coaches share their book advice for specific situations in work and life.

Ever wonder what the coaches at Reboot suggest to their clients for specific situations in work and life? Wonder no more!

In addition to the eight practical-tactical books Reboot recommends most often, here is a quick list of the books our coaches suggest to their clients who find themselves dealing with issues such as building companies rooted in values that are operationally effective, models of leadership that are relational and human-centered, a guide for managers, having hard conversations, brand building, storytelling, how to think about sales, asking good questions, ways to think about leadership, the importance of being vulnerable, what to do when things fall apart, and skills for your key partnerships in the office and at home.

Wondering how to get the leadership team aligned, how to think about meetings, hiring, and vision? Wondering what it takes to get everyone engaged and on the same page? Wondering what clarity looks like, and how to get it? Run, don’t walk, to get your hands on The Advantage: Why Organizational Health Trumps Everything Else in Business, by Patrick Lencioni. Then, buy a copy for everyone on your leadership team.

New to management, or have a bunch of new managers? Get them all a copy of The Making of a Manager: What to Do When Everyone Looks to You by Julie Zhou.

Looking for a model of leadership different from the more traditional model of command and control style? Reboot coach Andy Crissinger recommends Humble Leadership: The Power of Relationships, Openness, and Trust, by Ed Schein. If all you’ve ever seen and experienced is command and control leadership styles, this book offers a different mental model for leadership that is relational and human-centered.

Curious how those relational and human-centered behaviors play out in an organizational system? We recommend Conscious Business: How to Build Value Through Values, by Fred Kofman, for a deeper dive into the way to do business and build companies that can be rooted in values and also be operationally sound and effective.

Finding yourself mildly skeptical about vulnerability in leadership? Wondering why and where it is so crucial in good leadership? Check out Dare to Lead: Brave Work. Tough Conversations. Whole Hearts., by Brené Brown.

Need to understand your business better by the numbers? We recommend Managing By The Numbers: A Commonsense Guide To Understanding And Using Your Company’s Financials by Chuck Kremer and Ron Rizzuto.

Getting ready to scale? There’s rarely a better handbook than The High Growth Handbook: Scaling Startups From 10 to 10,000 People, by Elad Gil.

Get ready to step into some hard conversations. Reboot coach Courtney Joyce recommends getting your hands on Crucial Conversations: Tools for Talking When Stakes Are High, by Kerry Patterson and Joseph Grenny, and Radical Candor, by Kim Scott. (We also highly recommend Non-violent Communication: A Language of Life, by Marshall Rosenberg.)

Looking for an effective sales methodology? Reboot Coach Jeff Riddle recommends The Challenger Sale: Taking Control of the Customer Conversation, by Matthew Dixon and Brent Adamson.

Creating a vision for everyone to get behind? Getting your pitch together for future investors? Find Your Red Thread, by Tamsen Webster, is great for storytelling whether you’re a CEO creating a vision that brings everyone together and/or about to fundraise.

Wondering what it is like leading a team? Reboot Coach Ray Foote recommends picking up Yes to the Mess: Surprising Leadership Lessons from Jazz, by Frank Barrett. Barrett uses Jazz as a metaphor for leadership and being on a team. This book stresses the importance of presence, listening, and generosity when creating, collaborating, and innovating in a band, er, team.

Building a brand? The Hero and the Outlaw: Building Extraordinary Brands Through the Power of Archetypes, by Margaret Mark and Carol Pearson, looks at the voice of your brand through the lens of twelve different archetypes.

“Part of becoming the leader you want to become is finding the consistent habits that lead to success,” notes Reboot coach Chris VandenBrink who recommends Atomic Habits: Tiny Changes, Remarkable Results, by James Clear. This book gives a good entry framework into how to accomplish this, as well as acknowledging identity as a variable that leads to good habits.

Are you a scaling information company composed of knowledge workers? Understanding the context of work at the current moment is essential where motivation is driven by more than carrots and sticks. Coach VandenBrink also recommends Drive: The Surprising Truth About What Motivates Us, by Daniel Pink, because understanding intrinsic motivators are essential in inspiring people to be their best.

Are you challenged by asking good questions as a leader? Pick up Quiet Leadership: Six Steps to Transforming Performance at Work, by David Rock. This book makes a compelling case that the difference between good and great leaders (and companies) is thinking with the people in your organization, not thinking for them.

Going through a particularly rough patch? We often recommend the wisdom in the pages of When Things Fall Apart: Heart Advice for Difficult Times, by Pema Chödrön. Good for guiding through any kind of chaos, this book is particularly recommended when a confluence of both work and life misfortunes are occurring.

New entrepreneur with a significant other who’s already tired of your entrepreneurial life? We often recommend starting with Startup Life: Surviving and Thriving in a Relationship with an Entrepreneur, by Brad Feld & Amy Batchelor. It may save your relationship.

Co-Founder issues? Other relationship issues related to the paragraph above? Check out The 7 Principles for Making Marriage Work, by John M. Gottman and Nan Silver. This can be an inroad for co-founder challenges as well as marital challenges and can help you build better partnerships.

(For some Reboot’s other recommended book lists, check out our list of unconventional (non-business) reads for those who identify as men and women.)



Allison Schultz
Reboot: Better Humans Make Better Leaders & Better Leaders Create Humane Workplaces.

Co-founder and coach @RebootHQ. Lifting up the wisdom of the equines for leaders of today so we can return to our truest self.