Curiosity. A lifelong interest in learning is one hallmark of a high-quality thinker.

Nikola Tesla himself said, “It is paradoxical, yet true, to say, that the more we know, the more ignorant we become in the absolute sense, for it is only through enlightenment that we become conscious of our limitations. Precisely one of the most gratifying results of intellectual evolution is the continuous opening up of new and greater prospects.”

Must-Read IT Management Books For Aspiring CIOs

Even if you’ve worked in IT for years, there’s still more to learn. Especially if you aspire to the CIO position, or you’ve found yourself recently promoted. Here are seven books aspiring CIOs should check out. All of them have a 4.5-star rating or better on Amazon, cost less than $50, and have been published in the last five years.

1. The Agile Handbook

Must-Read IT Management Books For Aspiring CIOs

The Enterprisers Project polled IT executives about the books had the most impact on them. They liked Agile IT Organization Design: For Digital Transformation and Continuous Delivery by Sriram Narayan.

John Marcante, CIO and Managing Director of Vanguard’s IT Division, recommended the book. “Beyond the technology enablers, the book dives into the organizational design and management culture needed to thrive in this agile world,” Marcante said.

To really get the benefits of agile, you must implement it beyond the programmers to the organization as a whole. Narayan has spent more than 15 years helping leaders in various industries implement agile software development holistically to help digital businesses achieve overall agility, not just development team agility.

On Amazon, reviewer Charles T. Betz wrote, “Deep. Wide. Credible. Current. All those adjectives apply.”

2. The Intro to Big Data

Must-Read IT Management Books For Aspiring CIOs

Paul Marshall, CFO and SVP of Operations, Influitive recommended Winning with Data: Transform Your Culture, Empower Your People, and Shape the Future by Tomasz Tunguz and Frank Bien. “It is relevant both to senior execs but especially for CIOs as they contemplate how they transition oceans of data and convert it into actionable intelligence for their organization,” Marshall said.

Tunguz is a SaaS-focused venture capitalist and partner at Redpoint. He writes about raising funds, startup benchmarks, management best practices and team building. Bien is President and CEO at Looker, a BI software company that builds “new data experiences.”

Winning with Data is all about how to harness the power of big data to improve your organization’s decision making and strategy. The authors focus on showing readers how to create a data-positive culture. Real-world examples include the story of how Warby-Parker disrupted a $13 billion monopolized market with the help of data. Other businesses profiled include ThredUp, Venmo, and HubSpot.

Michael Sutton wrote, “If you’re looking to get an initial introduction into data-driven companies or how you might bring data-driven thinking to your company, Winning with Data is for you.”

3. The How-to-Lean Book

Must-Read IT Management Books For Aspiring CIOs

Lean Enterprise: How High Performance Organizations Innovate at Scale by Jez Humble, Joanne Molesky, and Barry O’Reilly is a Harvard Business Review must-read for would-be CEO’s.

Jez Humble brings a decade of IT experience, having worked in developer, systems administrator, trainer, consultant, manager, and speaker roles with myriad platforms and technologies. His consulting work includes nonprofits, telecoms, financial services, and online retail companies. He is co-author of Continuous Delivery. Molesky is a Principal Consultant and key member of with ThoughtWorks’ internal TechOps Management team. She helps with internal IT Governance Risk and Compliance and consults for clients on continuous delivery and process improvement, particularly as applied to controls, risk, and compliance. O’Reilly consults with enterprise companies on lean and agile and writes for The Economist.

Lean Enterprise helps CIOs of software companies learn lean and agile principles and implement them company-wide to move fast at scale. It’s a practical guide to getting better at responding to changing market conditions, customer needs, and emerging technologies.

Nic Grange, CTO of Retriever Communications, said of the book, “Whether it is to ensure the survival of their organization or to transform them into market leaders, this book is squarely aimed at IT and organizational leaders and how they can change their entire organization to adapt to the constant change in technology and customer demands.”

4. The Servant Leadership Book

Must-Read IT Management Books For Aspiring CIOs

Curtis Franklin Jr. at InformationWeek recommends Leaders Eat Last: Why Some Teams Pull Together and Others Don’t by Simon Sinek. It leads Franklin’s list of books for the CIO because “A really great team can define a career.” Capterra read Sinek’s 2009 book Start With Why as part of our company-wide book club.

In Leaders Eat Last, Sinek uses the Marine Corps mess hall as an example of servant leadership. Officers stand behind enlisted Marines in line for food. Part of being a leader is making sure your charges are taken care of. Read real-world examples of great leaders who fostered teamwork by creating the environments people naturally work well together in, and the accomplishments those teams achieved.

The central insight is that teams work best when they are led by people who care more about team success than careerism. “It’s a powerful lesson that this book brings home in interesting and compelling ways,” Franklin writes. The goal of the book is a team where all members wake up feeling inspired to work hard, feel trusted to make decisions throughout their day, and go home feeling fulfilled at night.

5. Learn the Psychology of Leadership

Must-Read IT Management Books For Aspiring CIOs

Bill Wilson, founder of Alcoholics Anonymous, famously said, “You can’t think your way into right action, but you can act your way into right thinking.” Act Like a Leader, Think Like a Leader by Herminia Ibarra is a treatise on how that works and how to apply it to leadership. Ibarra is a professional leadership and development expert and professor at leading international business school INSEAD. The key is making small, incremental changes in the way you work. Learn to stop doing those urgent-but-unimportant tasks and start making time to lead in small ways.

The premise is simple. If you want become a leader, start by leading. “This book might just be the book that lets you finally make some of the leadership shifts you’ve been wanting to make,” Franklin writes. Especially if you’ve tried beginning to lead by changing your thought patterns and that’s not working for you.

6. Learn Team-Building From Google

Must-Read IT Management Books For Aspiring CIOs

“I think this is a must read for any leader in a modern business,” wrote Otis Chandler at GoodReads of Work Rules!: Insights from Inside Google That Will Transform How You Live and Lead by Laszlo Bock. Workplace rankings consistently place Google among the best organizations to work in the world. Written by the head of Google’s people team, Work Rules! reveals what 15 years of experience in HR research and development have taught Bock and how he’s applied recent research in behavioral economics and psychology to Google’s HR functions.

“Google has done a lot of things right both in their products and also in how they run their company and build their culture, and this is a fairly detailed account of how they’ve built an impressive culture, and is written by someone who knows – their head of HR,” Chandler wrote. “I’m a little surprised he told as much as he did – but I suppose it will only help for recruiting.”

It’s not just Google-focused though, containing stories of famous companies with horrible culture and obscure companies that achieve record profits by listening to their people and treating them like they’re valuable.

“In some ways this is the perfect book for a CIO to read because many of the practices Bock describes will be impossible without executive support,” Franklin writes. “That said, if you’re someone who’s not yet the CIO, but hopes to have the title in the future, then this book is one you should read and understand. If nothing else, it will give you the information to compare what your organization is doing to what Google does, and a reason to ask which way is superior for your team.”

7. The Army Gets Agile

Must-Read IT Management Books For Aspiring CIOs

Team of Teams: New Rules of Engagement for a Complex World by General Stanley McChrystal, Tantum Collins, David Silverman, and Chris Fussell is the only management book for aspiring CIOs co-written by a retired four-star general. His co-authors are two former Navy SEALs and a former student of Gen. McChrystal’s leadership course at Yale.

While books like Leaders Eat Last take their cues from the military and apply them to business,  Team of Teams shows how the military adapted to a modern, more dynamic, environment.

The book is, according to the Wall Street Journal, the story of how Gen. McChrystal “transformed an elite U.S. military organization from a traditional command-and-control setup to a distributed, collaborative operation.” In 2004, Gen. McChrystal began to oversee the fight against terrorist insurgencies in Iraq.

After assessing the situation, he declared that the task he faced more closely resembled “a Fortune 500 company trying to fight off a swarm of start-ups” than with “the Allied command battling Nazi Germany in World War II.” What he found was that warfare had changed dramatically. And the insurgents (mainly al Qaeda) weren’t succeeding because their training or tactics were superior to that of the US military. Instead, their nonhierarchical structures were better suited to modern warfare.


Any books I left out? Let me know in the comments!

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