Are you an aspiring IT leader? Read these six books.

by Stephen Danos

IT departments are complex machines. To handle the challenges of tomorrow, the next wave of IT leaders will need technical prowess, intrapersonal skills, and a deep understanding of their respective businesses.

Considering how the role of IT is changing, if you want to gain management experience, you need to position yourself to fulfill the evolving and intricate needs of end users. So whether you specialize in operations, infrastructure, business solutions, systems, or technical project management, continuously learning can give you the edge you need to move up.

As you plan your professional goals for 2020, these books will help you make strides toward a role in IT management. At the very least, they’ll push you to create more conversations with your peers, your manager, and IT leaders within your company. And who knows? After you finish these titles, you might just teach them a thing or two. 

The CIO Paradox

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

Martha Heller, who is CEO of Heller Search Associates, is the author of two books: The CIO Paradox: Battling Contradictions of IT Leadership and, most recently, Be The Business: CIOs in the New Era of IT

In the former, Heller defines the CIO paradox quite simply: if CIOs are hard-working, rational, smart, and highly capable leaders, then why do they tend to “inherit a mess” when joining a new company? 

“Is it human nature to trash what has come before us? Or is there something inherently problematic about the CIO role that even talented, intelligent, and experienced leaders have trouble making it work?”

Throughout the book, Heller dives into several paradoxes that put IT leaders at odds with the systems they inherit and how they work around them. By reading, you can see how seemingly opposing concepts stack up against each other — whether it’s operations versus strategy, accountability versus ownership, cost versus innovation, or IT’s relationship to the entire business. 

The book is teeming with real-life examples of how IT departments have evolved at enterprise-level companies. She also wraps each chapter up with conclusions that summarize how you can improve the legacy of your IT department through actionable suggestions.

Measure What Matters

2. Measure What Matters by John Doerr

On the book’s official website, Measure What Matters is marketed as “a handbook for setting and achieving audacious goals.” This book covers the objectives and key results (OKR) framework—which differs from KPIs—and how to use it effectively for goal-setting and improving collaboration through transparency. 

Doerr, a venture capitalist and investor, shares working examples from big-time organizations, such as Google, The Bill and Melinda Gates Foundation, and Intuit, including his initial pitch of OKRs to Larry Page and Sergey Brin at Google’s Silicon Valley headquarters in 1999. In the midst of recounting this presentation, Doerr reveals his position on goal setting:

“An effective goal management system—an OKR system—links goals to a team's broader mission. It respects targets and deadlines while adapting to circumstances. It promotes feedback and celebrates wins, large and small. Most important, it expands our limits. It moves us to strive for what might seem beyond our reach.”

With his mantra in tow (“Ideas are easy. Execution is everything”) Doerr shows how OKRs can function across industries and disciplines, for organizations, teams, and even individuals. In the second half of the book, Doerr thoughtfully examines the impact of OKRs on annual performance reviews, continuous improvement, and company culture. Also, I highly recommend that anyone interested in OKRs and goal-setting check out Doerr’s 12-minute TED Talk.

IT pros, teams, and departments could benefit from adopting OKRs to measure what matters to them during 2020. For example, if your security team has an objective of improving security protocols, key results could include maintaining 99.9% uptime or conducting controlled external threat tests in order to strengthen the internal software.

Servant Leadership in Action

3. Servant Leadership in Action by Ken Blanchard and Renee Broadwell

Have you heard of servant leadership? This form of leadership has formally been around for decades, prioritizing listening, coaching, empathy, stewardship, and employee growth. In this collection of essays, carefully curated by Ken Blanchard and Renee Broadwell, over 40 leaders tackle concepts related to being a servant leader. 

For example, Brené Brown, the popular researcher and storyteller, discusses in her essay how “leaders must dare to rehumanize education and work” within this framework:

“This means understanding how scarcity is affecting the way we lead and work, learning how to engage with vulnerability, and recognizing and combating shame.”   

This tome is great if you want a 360-degree view of servant leadership and all that it requires, including ample examples and a catalog of characteristics that define effective leaders who use this approach. IT pros, managers, and executives can read this book to learn from preeminent thought leaders, then apply those teachings to alter their department’s management strategy.

Be Our Guest

4. Be Our Guest - Perfecting the Art of Customer Service by The Disney Institute, edited by Theodore Kinni

As any IT leader knows, customer service is key to the department’s success. It’s paramount for you to obsess over end users, whether they’re external or internal customers. Be Our Guest is a formative study on how The Walt Disney Company aims to make every interaction with customers feel genuine, authentic, and delightful. It’s both a guide to customer satisfaction and a comprehensive history of the company. 

IT professionals working at every level can gain insight into creating a best-in-class customer experience that will work toward ultimately improving relationships with end users and leaders across the business. In addition, the book contains countless anecdotes and the occasional gem from Walt Disney himself: “Get a good idea and stay with it. Dog it, and work at it until it’s done right.”  

Truth from the Trenches

5. Truth from the Trenches: A Practical Guide to the Art of IT Management by Mark Settle

War analogy aside, Truth from the Trenches covers all-important IT topics like budgeting, recruiting, innovation, understanding demand signals from your company, and how to foster reciprocal relationships with vendors. Settle, who has held CIO positions for seven different organizations including Okta and BMC Software, digs deep into his wealth of experience to give IT managers and executives what they need to be better leaders:

“A continuous management focus on chronic employee frustrations can pay major dividends. It underscores IT’s commitment to the success of its business colleagues and also showcases IT’s technical competence. The goodwill generated through a consistent focus on recurring employee concerns can offset negative IT perceptions that inevitably occur when major projects run over schedule or over budget, or when IT has insufficient bandwidth to address specific enhancement or project requests.”

This nugget from Chapter 6 underscores what many analysts and experts have been saying for years: that companies run better when IT and the business are in harmony. Reading first-hand stories and advice from Settle can help aspiring IT leaders learn practical ways to advance their careers and make high-impact contributions to your entire organization.

Life in Code

6. Life in Code: A Personal History of Technology by Ellen Ullman

In Life in Code, Ellen Ullman tells story after story that anyone in a technical role can relate to, cataloging her experience with prescient topics like computer programming, the internet, AI, and more. Her technical expertise is matched by her writing talent as she explores the era of the personal computer and the inextricable link between technology and humanity. Ullman’s memoir is to-the-point, overflowing with her experiences and memorable, thought-provoking lines:

“Pretty graphical interfaces are commonly called ‘user friendly.’ But they are not really your friends. Underlying every user-friendly interface is a terrific human contempt.”

Whether or not you agree with Ullman, the content throughout the book is engaging, well-written, and singularly unique. At the end of the day, IT pros will find wisdom in Ullman’s narratives, a trait that all leaders need if they want to succeed and coach the next generation of IT managers.

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