14 essential book recommendations by and for IT leaders

Looking for your next read? Why not pick up a book that will inspire you to be a more effective leader, help you spot challenges and pitfalls in your IT strategies and processes, or prepare for the future of information technology?

I asked CIOs and other high-level IT leaders to recommend books that have impacted their career, whether that has meant inspiring them to be better leaders or helping them navigate a particular challenge. This sort of transformative revelation might seem like a lot to expect from paper and ink (or e-ink) but printed language is where humans — even those who are building cutting-edge digital technologies for a living — still store our best ideas. And this group of CIOs, CTOs, and technical CEOs have strong favorites — books they turn to again and again for inspiration.

So, whether you are headed into a long flight or simply want to relax while filling your brain with ideas, add one of these titles to your bedside table or e-reader of choice.

For grasping artificial intelligence

Sherry Comes, former CTO at IBM Watson and current managing director of conversational AI at PwC, thinks you need to read Age of Invisible Machines: A Practical Guide to Creating a Hyperautomated Ecosystem of Intelligent Digital Workers (Wiley, 2022) by Robb Wilson. This thorough roadmap for negotiating the future of digital automation is written by the founder and chief technologist at OneReach.ai and the owner of UX Magazine.  

“This is the technology book every business and technology leader needs to read,” says Comes. “With each chapter, I found myself agreeing more and more. This made my ‘must-read’ list for anyone who cares about technology.”

For understanding teams

“CTOs and CIOs who work for organizations that are struggling to deliver value sustainably will greatly benefit from reading Team Topologies: Organizing Business and Technology Teams for Fast Flow (IT Revolution Press, 2019) by Manuel Pais and Matt Skelton,” says Peter Kreslins Jr., CTO and co-founder of Digibee.

This step-by-step guide to designing a high-functioning organization helps you understand four team types and interaction patterns and helps you to type and build it.

“It gives the fundamental patterns for achieving fast flow,” he says. “By defining team types, their fundamental interactions, and the science behind them, you learn how to better model your organizations according to these definitions. This book is mind-bending because it translates the complex theories behind the socio-technical aspects of software development and delivery into a set of easy-to-understand patterns. It also gives a set of streamlined steps to get started.”

Novels that entertain and teach

Kreslins Jr. also recommends two books by founder and former CTO of Tripwire Gene Kim.

The Unicorn Project: A Novel About Developers, Digital Disruption, and Thriving in the Age of Data (IT Revolution Press, 2019) tells the story of Maxine, a senior lead developer, as she tries to survive in a heartless bureaucracy overrun with paperwork and committees.

In The Phoenix Project: A Novel About IT, DevOps, and Helping Your Business Win(IT Revolution Press, 2013), Bill — an IT manager — takes over a critical project that’s over budget and behind schedule. The CEO demands that Bill deliver the project in 90 days.

“Both books talk about modern ways of delivering software,” says Kreslins Jr. “They touch the core of the issues that prevent organizations from delivering value without obstacles — generating a sense of purpose, meaning, and pride for everyone working on it. The great thing about both of these books is that they are novels that tell the story from the point of view of people struggling with their day-to-day jobs, as they are hindered by bureaucracy, unnecessary processes, and overall team dysfunction. The Phoenix Project, in particular, shed light on the DevOps movement that later became widely adopted in organizations.”

To learn leadership from the SEALs

Nageswaran Vaidyanathan, CTO of Duck Creek Technologies, enjoyed reading Extreme Ownership: How US Navy SEALs Lead and Win (St. Martin’s Press, 2017) by Jocko Willink and Leif Babin. Vaidyanathan believes any IT leader will benefit from reading this book about leadership from the ranks of the US Navy’s elite special operations force, known as the SEALs, for sea, air, land.

In the book, Willink and Babin write of being sent to Ramadi, Iraq — a violent war zone at the time — to secure the city. There they discovered that leadership is the element most essential to team success — even in the worst situations. They returned home to found the SEAL leadership training team.

“It talks about the competencies and leadership traits necessary to take ownership of a team and allow each member to do the same — and be able to make crucial decisions under pressure,” says Vaidyanathan. “I find it to be a great source for how to cultivate the right team competencies and individual leadership traits for dealing with stressful situations.”

To become future proof

Vaidyanathan also recommends The Industries of the Future (Simon & Schuster, 2017) by Alec Ross.

Ross was Senior Advisor for Innovation to US Secretary of State Hillary Clinton and traveled the world, visiting startup hubs and R&D labs, to uncover the latest advances that are emerging from every corner of the globe. In the book, he examines robotics, AI, cybercrime, genomics, big data, and more.

“It covers the different aspects of what will drive global transformation and how these will cause progress or failure,” says Vaidyanathan. “Ross also looks at how the global economic future will be shaped and the trends that will drive the way we live.”

For solving process issues

Andrey Ivashin, CIO at Dyninno, recommends three books that “hunt for answers and valuable advice in business areas where leaders frequently experience challenges,” he says. “They have each helped me at various points in my professional life.”

The first of which, The Goal: A Process of Ongoing Improvement (North River Press, 2014) by Eliyahu M. Goldratt, is a treatise on modern economic theory, packaged as a novel.

“It is a well-known book and a classic of business literature,” says Ivashin. “And because it is written like a novel, it is accessible and engaging. It offers helpful techniques and solutions for resolving typical corporate issues like bottlenecks, inefficiencies, and poor communication. The lessons you learn from the characters in the book can be applied to any business and it highlights the necessity for businesses to continuously enhance their processes to remain successful and competitive.”

For building culture

Ivashin also recommendsWhat You Do Is Who You Are: How to Create Your Business Culture(Harper Business, 2019)by Ben Horowitz because it “shows the importance of company culture and the role of leadership.”

Horowitz is a venture capitalist and management expert who uses history and modern organizational practice to offer advice on culture building.

“It offers helpful suggestions and examples of what does and doesn’t work in terms of creating a strong company culture,” says Ivashin. “I think it’s more significant that the author examines how leaders may foster a healthy work atmosphere and inspire people to perform at their highest level throughout the book.”

To understand the science of motivation

Ivashin also thinks IT leaders will enjoy Drive: The Surprising Truth About What Motivates Us (Riverhead Books, 2009) by Daniel H. Pink.

Pink is a New York Times bestselling author of seven books about work, creativity, and behavior and his books have sold millions of copies around the world.

“This book explores what truly motivates people, based on scientific research from psychology, economics, and neuroscience,” says Ivashin. “Pink points out that conventional motivational techniques, such as rewards and punishments, are less successful than we assume and might even be counterproductive. It shows that the three key motivation factors are autonomy, mastery, and purpose.”

For learning what drives trust

Rick Johnson, chief digital officer of Marvin, recommends The Four Factors of Trust: How Organizations Can Earn Lifelong Loyalty (Wiley, 2022) by Ashley Reichheld and Amelia Dunlop. This title breaks teaches you to measure, predict, and build trust.

“We need to really understand the drivers that influence customer and employee trust, as this is increasingly a litmus test,” says Johnson. “Those are the drivers we need to focus on and accentuate in our customer experiences as well as employee experiences — experiences that are shaped and delivered by technology. Technology leaders must be trusted by the enterprise. There must be trust that we are making the right technology decisions, designing and introducing technology that will work and deliver value, and trust in doing what we say we will do. It is imperative for technology leaders to be authentic, honest, candid, and transparent — in the pursuit of being trusted.”

To learn from historic leaders

Bill Bragg, CIO at SymphonyAI, recommends Inspiring Leadership: Learning From Great Leaders(THO, 2002) by John Adair, which breaks down the lessons learned by great leaders from history — Alexander the Great, Attila, Churchill, de Gaulle, Einstein, Gandhi, Sir Edmund Hillary, Ho Chih Min, Hsun-Tzu, Kennedy, Lao Tzu, and many more — so that today’s leaders can learn from them.

“It showed me the human physics we need to account for, and to value, when we decide how to focus our time,” says Bragg.

To inspire bold action

Bragg also enjoyed Do/Disrupt: Change the Status Quo. Or Become It (Chronicle Books, 2018) by Mark Shayler.

This advice book offers tips — as well as quotes from some of history’s most famous innovators — on how to be strategic and bold as you take your own path toward transforming your ideas into reality. “It is a fun and straight to the point guide or sketchbook,” he says. “It’s suitable for all seeking a brave new way.”

As a playbook for success

Barr Moses, CEO and co-founder at Monte Carlo, recommends Amp It Up: Leading for Hypergrowth by Raising Expectations, Increasing Urgency, and Elevating Intensity (Wiley, 2022) by Frank Slootman.  

“Frank Slootman, serial entrepreneur and CEO of Snowflake, shares his playbook for building a successful company,” says Moses, “having led Snowflake to the biggest software IPO ever. In his first book, he pulls no punches about the importance of speed and focus when leading a hypergrowth organization, as well as setting a high bar for the rest of your team. As co-founder and CEO of my own category-creating company in the data space, I found Slootman’s tactical advice and insightful perspective on what it takes to reach unprecedented scale to be a goldmine. 10/10; would — and often do — read again.”

For learning the power of lean software and DevOps

Rajesh Jethwa, CTO of Digiterre, suggests Accelerate: The Science of Lean Software and DevOps: Building and Scaling High Performing Technology Organizations (IT Revolution Press, 2018) by Dr. Nicole Forsgren, PhD, Gene Kim, and Jez Humble.

This book examines, through extensive research, ways that technology can drive business value.

“Backed by considerable research,” says Jethwa, “the book provides data-driven insights and practical guidance on how to improve technology delivery capabilities and foster a culture of continuous improvement to build high-performing teams.”

Practical, indeed.