2026 Recommended Reading List for Tech Leaders

This year’s list of books suggested by Heller Report readers includes titles aimed at IT executives in the AI and transformation trenches; titles that espouse lessons on leadership, team-building, interpersonal communication, corporate governance, and ransomware response; explainers on how we make decisions, form good habits (and avoid bad ones), and understand statistics about risk that guide decision-making; and a history of precision engineers. Happy reading!

(Listed alphabetically by author's last name. Titles link to Amazon.com page for the book.)

Barron’s Streetwise with Jack Hough
Barron’s Podcast

Recommended by Steven Rodichok
“If you’re looking for a sharp, practical listen, I’d recommend Barron’s Streetwise hosted by Jack Hough. While it’s not a book, this podcast consistently delivers thoughtful insights into markets, business trends, and leadership. What stands out is how frequently AI shows up in the conversation – not as hype, but as a real force shaping decisions across industries. It’s a good reminder that in today’s environment, every company is becoming a technology company, whether they realize it or not. It’s well worth adding to your rotation.”

The Impactful Technology Leader: Pursue Your Purpose to Innovate, Motivate and Inspire
by Chris Caruso

Recommended by Dan Roberts
“If you’re an IT leader looking for a book worth your time this summer, Chris Caruso’s The Impactful Technology Leader should be at the top of your list. What sets this book apart isn’t just the research spanning insights from 1,600+ leaders across 60+ countries, but the credibility behind it. Caruso writes from the vantage point of a proven CIO who has lived the realities of the role, not just theorized about them. He distills what truly separates good from great: the discipline to listen before acting, the ability to communicate in ways that connect technology to purpose, and the courage to consistently do the ‘next right thing.’ In a time when too many leaders are stuck on the technology treadmill, this book offers something far more valuable: a practical, experience-backed blueprint for driving innovation, building cultures people want to be part of, and leaving a lasting imprint on organizations and the next generation of tech talent.”

Reshuffle: Who Wins When AI Restacks the Knowledge Economy
by Sangeet Paul Choudary

Recommended by Anonymous
“If your leadership team is going to read one book about AI strategy this year, make it this one. Reshuffle reasons from first principles to explain how workflows will change and how these changes will rewire companies, alter competitive dynamics, and restructure industries. This is the conversation every C-suite needs to have.”

Atomic Habits: An Easy and Proven Way to Build Good Habits and Break Bad Ones
by James Clear

Recommended by Michael Goldberg
“In a compelling set of chapters, Atomic Habits presents a means for developing habits for improving your life and ways to decrease the habits you would like to stop.”

Storyworthy: Engage, Teach, Persuade, and Change Your Life Through the Power of Storytelling
by Matthew Dicks

Recommended by Jay Kreusch
“Storytelling is always mentioned in digital discussions, especially when it comes to executive or stakeholder change management. However, people rarely investigate the components of a good story. The lessons in this book, while focused on personal storytelling, give great insights into what makes a story impactful and stick. It has helped me polish my storytelling to stakeholders.”

The Next Conversation: Argue Less, Talk More
by Jefferson Fisher

Recommended by Raj Sadasivan
“Interpersonal communication is still relevant even in the AI world. This book helps people at all levels to increase awareness and communicate with intention.”

Building a Second Brain: A Proven Method to Organize Your Digital Life and Unlock Your Creative Potential
by Tiago Forte

Recommended by Sean Perry
“AI agents are all about context. How do you get an agent to know what you know? This book explains how to create a structured process that allows an agent to consume the same input you do. Then, not only do you get a consultant familiar with your context, but one that can consider multiple points of view.”

On Board: The Modern Playbook for Corporate Governance
by Jonathan F. Foster

Recommended by Eduard Sands
“The best operating leaders I know spend time learning the discipline of governance well before they need it. I picked up this book for that reason. Foster is direct, modern, and clear-eyed about what a board is for. It’s worth reading whether you sit on a board today or expect to in the future. I learned a great deal from Foster’s insights.”

Maxing Out: How to Get the Most Out of Yourself and Your Team
by Keith Fulton

Recommended by Dan Roberts
“Keith Fulton’s Maxing Out is the kind of book IT leaders should be reading because it’s built for real life. Structured into 42 crisp, two-page chapters, it meets leaders where they are: busy, stretched, and hungry for practical ways to get better quickly. Each vignette delivers a sharp, memorable insight drawn from an eclectic mix of sources, making it easy to digest, discuss, and apply. It’s tailor-made for team book groups looking to elevate leadership at every level, sparking conversations that translate directly into action. Fulton’s voice feels like a trusted operator in your ear, someone who’s been in the arena, translating experience into simple, actionable ‘next right things.’ Grounded in his own success as a CIO, Keith brings a practitioner’s lens to every page, offering not just inspiration, but a steady drumbeat of small, compounding moves that help leaders and their teams truly max out.”

Beyond the Hammer: A Fresh Approach to Leadership, Culture, and Building High Performance Teams
by Brian Gottlieb

Recommended by Gary Hoke
“For many IT leaders, the technical expertise that fueled their rise ¬– the instinct to grab the ‘hammer’ and fix the problem – eventually becomes a growth ceiling. Brian Gottlieb’s Beyond the Hammer identifies the precise pivot point where technical proficiency must give way to organizational design. This book provides a blueprint for transitioning from the most reliable troubleshooter in the room to its most effective strategist. Gottlieb offers a roadmap to shift focus from merely ‘keeping the lights on’ to architecting the systems, culture, and vision that empower a department to thrive autonomously. It is essential reading for leaders looking to move beyond the tactical weeds and elevate their impact from managing technical debt to driving measurable enterprise value.”

2034: How AI Changed Humanity Forever
by Kunal Gupta

Recommended by Rohinee Mohindroo
“2034 is a must read for business and technology leaders. This book shifts the conversation from tools and use cases to consequences and choices. Written as a look back from the future, it shows how AI reshapes power, work, identity, and leadership over time and forces readers to confront how today’s decisions compound into cultural and organizational outcomes. It is less about adoption and more about accountability, making it especially thought provoking for leaders responsible for governance, talent, and long term strategy.”

The CIO Paradox: Battling the Contradictions of IT Leadership
by Martha Heller

Recommended by Jennifer LaPlante
“I first listened to the audio version of this book when I was a new director of an IT PMO. It served me well over the years as a non-technical leader in an IT-heavy space. Over the years I built out my technology skills, but this book gave me the language to bridge business and IT.”

Vienna (song)
by Billy Joel

Recommended by Praveen Minumula
“I have recommended books the past few years, but this time it’s a song: ‘Vienna’ by Billy Joel. Originally written as advice to someone young, the song is a simple reminder to slow down and not feel like everything must happen immediately: ‘Slow down, you’re doing fine. You can’t be everything you want to be before your time.’”

Legacy: What the All Blacks Can Teach Us About the Business of Life
by James Kerr

Recommended by Anonymous
“James Kerr’s Legacy is a masterclass in high-performance culture, deconstructing the sustained success of the New Zealand All Blacks to reveal that true leadership is rooted in humility and character. By championing the practice of ‘sweeping the sheds,’ Kerr demonstrates that no one is too big to do the small things, while his ‘Blue Head’ framework offers a vital mental model for maintaining clarity and composure under extreme pressure. The book shifts the focus from individual talent to collective stewardship, challenging every leader to embrace the concept of ‘whakapapa’ –the responsibility to leave their organization in a significantly better place than they found it.”

The Phoenix Project: A Novel About IT, DevOps, and Helping Your Business Win
by Gene Kim, Kevin Behr, and George Spafford

Recommended by Raman Ranganathan
“The Phoenix Project is one of the most practical and engaging books for technology leaders because it translates complex IT and organizational challenges into a relatable story. It clearly illustrates how bottlenecks, misaligned priorities, and lack of visibility can cripple an organization and how applying DevOps principles can transform performance and culture. I recommend it because it helps leaders think systemically, improve cross-team collaboration, and focus on delivering real business value, not just technical output.”

Rewired: The McKinsey Guide to Outcompeting in the Age of Digital and AI
by Eric Lamarre, Kate Smaje, and Rob Levin

Recommended by Shaam Farooq
“I don’t recommend many ‘transformation’ books, but Rewired is worth a read. It moves beyond theory and lays out a practical operating model for turning technology into a value engine where talent, product model, and data are tied directly to business outcomes. For technology leaders and PE operating partners, it’s a useful baseline for driving real, measurable impact, not just activity.”

Recommended by Venkat Gopalan
“I recommend Rewired (Second Edition) because it provides a clear framework, hands-on advice, and proven approaches for scaling digital and AI in organizations. What stood out to me are the book’s concrete elements like focusing on a few priority domains, building cross-functional product teams, strengthening data foundations, and tracking value rigorously. The tangible case studies explain how leading companies move from pilots to scaled impact. In my work, this translates into prioritizing fewer high-impact domains, aligning teams around outcomes, and investing in capabilities that can be reused across initiatives. It shifted my focus from experimentation to disciplined execution. This book is especially valuable for leaders because it combines practical know-how with real examples, making it easier to apply.”

Recommended by Eduard Sands
“I do not read this book cover to cover. I use it when needed. When a CEO asks me what good looks like in a specific dimension of digital transformation, the chapter structure makes it easy to answer with something concrete instead of generic. Most books in this category are written to be read once and shelved. This one is so useful, it earns a spot on my desk.”

The Octopus Organization: A Guide to Thriving in a World of Continuous Transformation
by Phil Le-Brun and Jana Werner

Recommended by Eduard Sands
“Most transformation books treat change as a project with a start and an end. This one treats it as the operating state. That reframe stuck with me. Once you accept that change is permanent, the questions you ask about organizational design get sharper.”

The Undoing Project: A Friendship That Changed Our Minds
by Michael Lewis

Recommended by Eduard Sands
“What I love about Lewis is that he gives you the information and lets you draw your own conclusions. The Undoing Project tells the story of Kahneman and Tversky and the science behind how we make up our mind, but the book never tells you what conclusions to draw. This rare book makes you a sharper thinker without telling you what to think.”

Locked Up: Cybersecurity Threat Mitigation Lessons from A Real-World LockBit Ransomware Response
by Zachary Lewis

Recommended by Anonymous
“Locked Up delivers a gripping, first-person account of how a university squared off against one of the world's most infamous ransomware groups: LockBit. You'll walk through the author's personal experience battling – and negotiating with – LockBit, as well as the strategies, tools, and approaches he used in resolving the crisis. The book is a detailed, darkly funny, behind-the-scenes account of an increasingly common and feared event for organizations of all types and sizes. It offers up-to-date advice for people tasked with preventing, responding to, and recovering from ransomware attacks.”

Call Sign Chaos: Learning to Lead
by Jim Mattis and Bing West

Recommended by Linda Marie Arredondo
“Far removed from technology, this memoir provides battle-tested leadership strategies that provide the reader a break from technical jargon and industry stereotypes. Mattis divides his book into three sections: direct leadership, executive leadership, and strategic leadership. Each section provides pragmatic guidance based on real world experience in a time when the stakes couldn’t be higher. The knowledge gained from this book easily translates from the situation room to your next board meeting.”

Zero to Hero: The Human Experience in Leadership and Business Transformation
by Nora M. Osman

Recommended by Rob Zelinka
“Over the course of my career, I’ve seen countless initiatives fail – not because the technology was wrong, but because the human element was ignored. Zero to Hero is a vital corrective for the modern leader. Osman captures a truth I’ve lived throughout my career: leadership isn't a series of transactions but a commitment to the human experience.”

The Book of Why: The New Science of Cause and Effect
by Judea Pearl and Dana Mackenzie

Recommended by Bernardo Tavares
“The Book of Why goes beyond statistics, introducing a new science for understanding cause and effect. Pearl's ‘Ladder of Causation’ is a missing link between predicting outcomes and prescribing interventions, a timely topic considering what’s next for AI and autonomous systems. The author introduces new tools for codifying knowledge and reaching an understanding of why things happen. I recommend it to anyone driving enterprise AI strategies where 'digital workers' are being deployed and expected to be safe, effective, and explainable at all times.”

Normal Accidents: Living with High-Risk Technologies
by Charles Perrow

Recommended by Adam Frisbee
“In complex systems, failure is not a risk to mitigate; it is a condition to manage. Accidents are normal. Perrow lays out an idea that should unsettle every tech leader: systems defined by complexity and tight coupling, which is to say most of what we build, are guaranteed to fail. The only variable left is whether we survive it.”

Your AI Survival Guide: Scraped Knees, Bruised Elbows, and Lessons Learned from Real-World AI Deployments
by Sol Rashidi

Recommended by Thena Alagappan
“Rashidi discusses the practical challenges that come with implanting AI in enterprises and how to develop a good strategy and execute it well. The book offers great tips from a practitioner who has ‘been there and done that.’”

Good Strategy/Bad Strategy: The Difference and Why It Matters
by Richard Rumelt

Recommended by Ramesh Sreeram
“This book teaches how to cut through ‘corporate fluff’ to focus on identifying the most critical leverage points in an organization's complex system.”

Digital Trailblazer: Essential Lessons to Jumpstart Transformation and Accelerate Your Technology Leadership
by Isaac Sacolick

Recommended by Derrick A. Butts
“Digital Trailblazer provides a different perspective on innovative technologies and how they are used and viewed in the business world.”

Recommended by Martin Davis
“A fantastically practical book for CIOs and Senior IT people undertaking digital.”

Recommended by Joanne Friedman
“Edutaining, informative, and great storytelling for a book on digital transformation.”

Recommended by Liz Martinez
“This book is an excellent guide for leaders who are, or want to be, on the forefront of the technology revolution.”

Recommended by Joseph Puglisi
“Digital Trailblazer is a very practical handbook and an easy read. It should be required reading for every up-and-coming CIO (and perhaps a few already in the role, too).”

The Flaw of Averages: Why We Underestimate Risk in the Face of Uncertainty
by Sam L. Savage

Recommended by Edmond Momartin
“This book is exceptionally relevant for those who compile statistics for the executive dashboards and help avoid relying on stats that are commonly used yet don't provide a realistic measure of risk or avoid systematic errors.”

Know What Matters: Lessons from a Lifetime of Transformations
by Ron Shaich

Recommended by Scott Lovejoy
“Shaich shares the lessons he learned as he built Au Bon Pain, Panera Bread, and became involved in Cava Grill. The book contains quick, thought-provoking lessons for building and pivoting a business from startup to beyond the IPO. Shaich goes against conventional wisdom at times and proves he is human. He talks through the trade-offs when trying to balance his personal and business lives and how he learned what really matters.”

The Coming Wave: AI, Power, and Our Future
by Mustafa Suleyman

Recommended by Mayur Khare
“The Coming Wave by Mustafa Suleyman is valuable because it not only explains how AI and biotech will reshape the world, but it also frames the next decade as a race between innovation and control. Whoever figures out how to contain these technologies responsibly will define global power. The book pushes you to think not just about opportunity, but about governance, risk, and your own role in that balance.”

Future Shock
by Alvin Toffler

Recommended by Adam Frisbee
“A tech leader's real job is to operate inside a condition of permanent acceleration and change. Toffler’s core idea is simple: society is changing faster than humans are equipped to process. That gap creates stress, bad decisions, and sometimes institutional failure. Future shock is the anxiety we feel when there is too much change in too short a period. Written in 1970, this book is eerily timely in the age of AI.”

The Perfectionists: How Precision Engineers Created the Modern World
by Simon Winchester

Recommended by Praveen Minumula
“I liked how this book traces the quest for perfectly precise measurements, from early instrument makers to the technologies that made jet engines and semiconductors possible. It is a good reminder that most big innovations come from getting the small details right over time.”