Strategic Reading for Strategic Leaders: Tailored Book Recommendations for New SaaS CEOs

I’ve posted a few times about tools for SaaS CEOs (including here, here, and here). A related question people ask is what books new CEOs can read to support their learning and development. I have a go-to answer to that question, which references a long list of our team’s favorite business books. But I’ve become increasingly uncomfortable with such a blanket response to what is almost always a more targeted question (something about swatting a fly with a sledgehammer).

Because time is our most valuable commodity, life is too short to read business books that are only tangentially relevant to a specific skill we’re trying to develop or a challenge we’re trying to tackle. With that in mind, this post is intended to provide a more nuanced and actionable set of book recommendations for aspiring SaaS CEOs. To do that, it leverages Lock 8’s CEO Developmental Rubric (explained in detail here, with a summary image immediately below). What follows is a set of book recommendations that map directly to the eight core disciplines outlined within the CEO rubric, and a quick comment on why each book is well worth the investment of time to read.

1. Team Building / Leadership:
   • The Culture Code: The Secrets of Highly Successful Groups by Daniel Coyle
     • Why It’s Worth the Investment (“WIWI”): “We all want strong culture in our organizations, communities, and families. We all know that it works. We just don’t know how it works.” This book demystifies how to build strong, winning cultures by sharing real-world examples from many different arenas. This is a must-read for any people-centric leader.
   • The Five Dysfunctions of a Team by Patrick Lencioni
     • WIWI: First, this book is old-but-gold. It’s also super-short, so it’s easy to bang out in one night. And please don’t be put off by the book’s seemingly negative title; this parable-style guide offers a simple but elegant framework that will strengthen even the highest-functioning teams. Just be prepared to confront some uncomfortable mistakes that most of us have made along the way on our leadership journey.

2. Strategy Alignment and Vision:
   • Turning the Flywheel: A Monograph to Accompany Good to Great by Jim Collins
     • WIWI: Again, this one is a super-quick read – under 40 pages total. But it is packed with strategic value. Collins offers a pragmatic and easily actionable approach to strategy. “Flywheel” shows how disparate strategic elements fit together to create irresistible momentum. This tiny pamphlet is indispensable for CEOs looking to drive organizational alignment, clarity, and focus.
   • Inspired: How to Create Tech Products that Customers Love by Marty Cagan
     • WIWI: This is one of those books that is worth reading not just once, but every year or so – there are new learnings every time. Some might quibble that this is a book about product management, NOT about Vision and Strategy. I’d counter that for SaaS businesses, building successful product organizations that discover and deliver software that customers love is THE critical element of strategic alignment. This book is the best I’ve ever read on that topic.
   • Honorable Mention: The Crux: How Leaders Become Strategists by Richard P. Rumelt

3. Execution / Time & Resource Management:
   • Leading Change by John P. Kotter
     • WIWI: This book lays out clearly, and with rigorous supporting research, the 8-step process that has been proven to consistently work in terms of delivering successful projects, plans, and change initiatives. Any leader with a change agenda should learn and follow these steps. When initiatives have veered off-course (as they inevitably do), it is because I’ve botched or skipped one or more of these steps. Seriously.
   • The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter by Michael D. Watkins
     • WIWI: An indispensable guide for new leaders who wish to succeed in their expanded role…and who are willing to invest time and effort to do so. But this is more than just a book about managing a transitional on-boarding period. Rather, it helps leaders establish lasting credibility and execute over time to deliver substantive long-term value.
   • Honorable Mention: Predictable Success: Getting Your Organization on the Growth Track - and Keeping It There by Les McKeown

4. Communications
   • You're Not Listening: What You're Missing and Why It Matters by Kate Murphy
     • WIWI: If you buy the argument from this prior post, a critical role of the CEO is as the Chief Conversation Officer. You can’t have good conversations if you aren’t listening. Murphy makes an extremely compelling case for why we all (and especially leaders) need to stop talking and start listening; and she provides useful guidelines for improving in this critical and surprisingly-difficult-to-master skill.
   • Language and the Pursuit of Leadership Excellence: How Extraordinary Leaders Build Relationships, Shape Culture and Drive Breakthrough Results by Chalmers Brothers and Vinay Kumar
     • WIWI: This book was recommended to me by a world-class communicator, Robert Morton. Reading it was like a cheat-code on some of the practices that make him so consistently effective. But be prepared; unlike many of the books on this list, this is a meaty project that demands commitment.

5. Analysis / Quantitative Assessment:
   • Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts by Annie Duke
     • WIWI: My colleague Tim Blomfield calls Annie Duke “an American hero,” and I agree. This book nails the situation that CEOs face every day (they never have all the facts) and the analytical approach that enables successful CEOs to navigate this world of gray. It also provides valuable tools that CEOs can use to make better decisions, avoid counterproductive biases, develop truth-seeking habits, and remain calm and compassionate in the process.
   • The Visual Display of Quantitative Information by Edward R. Tufte
     • WIWI: This book is essential for any CEO, but particularly those who are anxious about leveraging data to manage their board of directors. Telling stories with data is a developed (not innate) skill for most of us; and this book can help anyone improve in this realm. You can present data in many ways; this helps execs make the best choices to accurately and understandably present the story they’re trying to tell.

6. Learner / Owner Mindset:
   • Mindset: The New Psychology of Success by Carol S. Dweck
     • WIWI: This may be the least surprising book on this list. Millions of people have already read it, and with good reason. The truth is that CEOs are wrong more often than they’re right; it’s important to make peace with this fact…even to embrace it. This book made that possible for me. It is no stretch to say that it fundamentally changed me both as a leader and just as a person trying to navigate through a world.
   • It’s Your Ship: Management Techniques from the Best Damn Ship in the Navy by Captain D. Michael Abrashoff
     • WIWI: Scaling any organization relies upon leadership…and followership. Many “pacesetter” leaders conduct themselves with impressive discipline and productivity; but they sometimes fail to empower others to think as owners, act with agency, and make decisions in service to the greater good. “Ship” offers a case study and digestible “how-to” to aid aspiring leaders in this crucial area.

7. Resilience
   • The Hard Thing About Hard Things: Building Businesses When There Are No Easy Answers by Ben Horowitz
     • WIWI: This book bucks the trend of obsessively celebrating huge success stories. Horowitz offer hard-earned wisdom from a world that SaaS leaders know well – one where adversity is everywhere, and the best available option is merely the “least-worst” one. I read this book during one of the toughest stretches of my career…and it was invaluable in getting through the hard stuff. Far more so than the countless success stories one finds every day on LinkedIn and the trade press, this book gets what CEOs are going through…and helps them do it. Plus, there are amazing quotes from hip-hop artists sprinkled throughout.
   • The Courage to Be Disliked by Fumitake Kogo and Ichiro Kishimi
     • WIWI: Being a CEO is often a lonely and isolating endeavor. They are responsible for balancing the needs of multiple sets of stakeholders; and leaders that seek to please everyone please no one. Through an engaging dialogue format, this book offers an introduction to Adlerian philosophy, which advocates living a fulfilling life without worrying about the past or future. CEOs certainly require intellectual and emotional courage; and this book provides tenets in support of remaining brave even in the face of powerful opposing forces.
   • Honorable Mention: How to Think Like a Roman Emperor by Donald J. Robertson

8. Creativity / X-Factor:
   • The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success Outsiders by William N. Thorndike
     • WIWI: This chronicles the achievement of a collection of legendary CEOs, each of whom had an undeniable “X-Factor.” They were fiercely unorthodox; and they delivered astonishingly impressive returns to investors. But this is far more than a hero book. It introduces the concept of CEO as capital allocator and offers both encouragement and examples around how thinking differently can yield massive results. This is a valuable counterpoint to many of the arguably more traditional books on this list.
   • Seeing What Others Don’t: The Remarkable Ways We Gain Insight by Gary Klein
     • WIWI: “Eureka!” moments don’t come exclusively from spontaneous inspiration. We can also program for optimizing insights. This is a fun book that talks about when and how this occurs.