7 Management Books Every CIO Must Read

Like IT tools and resources, management skills and practices are continually evolving. Unfortunately, as time-squeezed IT leaders struggle to keep pace with a seemingly-endless flood of disruptive technologies, many continue to rely on management philosophies and practices that were discarded and replaced many years ago.

Shedding outdated management approaches and acquiring fresh skills requires an open mind and a willingness to consider both new viewpoints and practices that have withstood the test of time. Here’s a look at seven management books that CIOs should read to remain productive and relevant in an ever more competitive IT and business arena.

1. Drive, by Daniel Pink

John Heveran, CIO of global risk solutions at Liberty Mutual Insurance, says he agrees with Daniel Pink’s assertion in Drive that many long-standing motivation lessons are actually misguided and often miss the mark. “He provides a series of interesting stories and, more importantly, true experiments to help back up his overall premise that how we have been thinking about incentives and disincentives are wrong,” Heveran explains.

The book proposes thinking about motivation in terms of autonomy, mastery, and purpose. “Applying these [lessons] to how tech teams organize and are encouraged is valuable,” Heveran says. “This is true of a tech team or an agile squad.”

Pink asserts that most leaders wrongly believe that the best way to motivate people is with rewards, such as money. He proposes that most individuals have a deep-seated need to perform well, and it’s up to leaders to tap into this desire.

Heveran says that Drive taught him there’s no need to look over shoulders or micromanage. “Encourage your teams to invest in themselves and each other, celebrating the passions of learning, perfecting new technologies with freedom, and [having] the time to experiment, share experiences, and build a mastery of their craft,” he advises. “The concepts of Drive really create a great blueprint around which we, as CIOs, can rally.”

2. Turn the Ship Around, by L. David Marquet

Turn the Ship Around details how naval commander L. David Marquet was able to transform his submarine from worst to first in the U.S. fleet during a time of great uncertainty, low morale, and stretched resources. Marquet’s approach was to jettison the traditional leader-follower management model in favor of a leader-leader configuration, a template that happens to align closely with agile philosophy.

The book emphasizes strong project governance principles while empowering all team members to think and act like leaders, solving the problems they’re closest to.

“This can be done by flagging intent to your team, rather than giving direct orders, ensuring your people have the right skills to effectively carry out their roles, preparing them to take autonomous action through experimentation and iteration, and helping them understand how their role in the project contributes to the whole,” explains Rajesh Jethwa, CTO at big data platform developer Digiterre. “Marquet uses practical examples from below the deck that can be easily applied to high-risk, high-profile and time-constrained software and technology projects.”

3. Eat Sleep Work Repeat, by Bruce Daisley

Kim Anstett, CTO of data and records management firm Iron Mountain, says that Eat Sleep Work Repeat was one of the most useful books she read during the pandemic. “It has had a really positive impact on how my teams and I work together every day,” she reports.

Offering “thirty hacks for bringing joy to your job,” author Bruce Daisley claims that it’s possible to transform a workplace from a bland, unimaginative environment into a fulfilling, fun, more engaged and, ultimately, successful place. Anstett particularly likes Daisley’s suggestions of holding “Silent Meetings” and occasionally shifting into “Monk Mode.”

During silent meetings, teams are encouraged to collaborate on a Google Doc or similar interactive platform instead of viewing a set of slides while listening to a speaker. “We then discuss and evaluate the inputs,” Anstett says. “Silent meetings get all attendees to participate and share their ideas instead of having one voice dominate the conversation.” She concludes that the approach is “far more productive and engaging than many of our in-person, pre-pandemic meetings.”

4. The CIO Paradox, by Martha Heller

Scott Caschette, CIO of Schellman & Co., an independent security and privacy compliance assessor, says that The CIO Paradox is a “must read” for any CIO, since “you can lean on it in tough times, knowing that you’re not the only one facing the same challenges.”

Author Martha Heller, who has worked extensively with IT leaders, believes that CIOs today are facing a set of inherent contradictions, such as “cut costs, but be innovative,” “boost security, but don’t increase budget,” and “adopt new technology, but support the past.” Heller claims that CIOs who recognize and resolve these contradictions can position themselves to become a sought-after commodity.

“What’s great about this book,” Caschette says, “is the realization that there’s a certain camaraderie among CIOs and within our circumstances.”

5. Hit Refresh, by Satya Nadella

The Microsoft CEO’s insights on the power of the cloud and the value of ecosystems is truly visionary, and Hit Refresh does a great job at explaining how Nadella drove his vision through to execution, says Sanjay Srivastava, chief digital officer at professional services firm Genpact. “His views on the ethical use of AI are particularly relevant today,” Srivastava notes.

Across its pages, Hit Refresh focuses on how leaders and organizations must periodically transform themselves in order to generate new energy, create fresh ideas, and sustain continued relevance and renewal. On a personal level, Srivastava says he related to Nadella’s journey from India to the US and the Microsoft chief’s passion for curiosity and continuous learning.

6. Radical Candor, by Kim Scott

Subtitled “Be a kickass boss without losing your humanity,” Radical Candor draws on Scott’s experience leading teams at Google, Apple, and other major tech industry businesses. Scott advocates nurturing a workplace culture in which leaders care deeply about their teams, and regularly challenges them to be their best.

Scott proposes that a seven-step executive methodology — listen, clarify, debate, decide, persuade, execute, and learn ― allows teams to perform tasks faster and more efficiently. She also believes that open communication is essential for long-term management success.

One of the hardest tasks for any IT leader is providing honest feedback on mission, performance, and other key issues, states Charles Edge, CTO of startup investment firm Bootstrappers.mn. “Radical Candor helps us see why not doing so is a huge mistake,” he says. “[Scott] provides a number of examples from her time working for [Facebook COO] Sheryl Sandberg and others that arms a reader with ways to phrase feedback that helps grow those around us.”

7. How to Win Friends and Influence People, by Dale Carnegie

Dale Carnegie’s venerable How to Win Friends and Influence People was written 85 years ago, yet it’s indispensable wisdom applies as much today as it did when it was first published, states Greg Flint, CTO of Four13 Group, a software development consulting company specializing in e-commerce platforms and tools.

While Carnegie’s entire book is filled with helpful insights, Flint says that two chapters should particularly resonate with IT leaders. “Nine Ways to Change People Without Giving Offense or Arousing Resentment” provides valuable advice on staff leadership, he notes. Meanwhile, “Twelve Ways to Win People to Your Way of Thinking” provides technical leaders at any level with a number of helpful concepts that can help gain buy-in with peers in other parts of the organization.

“It’s a master class in understanding how to work with others to get things done within an organization,” Flint says.