Book review: The CIO Paradox: Battling the Contradictions of IT Leadership

It’s a universal trait, it seems: we all want to be understood, want the world to see things through our eyes, want to watch the “aha” light go on when people finally realize just how tough we have it and how magnificently we still prevail.

IT people, and senior technology executives in particular, are anything but exceptions to this longing. In fact, it seems that very few other disciplines have to put up with a constant stream of articles and books questioning our very existence, approaches, purpose, and worth (Does IT Matter?, the death of the CIO , etc.). Even the acronym CIO is commonly and gleefully referred to as standing for “Career Is Over”. And you want a downer? Just try googling “average tenure of the CIO”.

A person could downright get a complex here. No one seems to get it! No one understands how tough a job this is! No one seems to perceive the “damned if we do, damned if we don’t” intrinsic nature of our role. I present this syndrome with all due humor (“against the assault of laughter nothing can stand”, said Mark Twain), but I also mean it: is it utter masochism that leads us to choose this “whipping boy” kind of career at this level?

The CIO Paradox, book cover
That’s why it’s so welcome when a book comes along that effectively presents insight and understanding into the “big picture” struggles of today’s CIO, even combined with empathy and warmth. Martha Heller’s The CIO Paradox: Battling the Contradictions of IT Leadership, just out late last year, brims with “been there seen that” deep insight into many of the standard CIO predicaments.

Heller achieves this effect via a brilliant unifying theme: per the title, the “CIO Paradox.” She examines dozens of aspects of the CIO role and with astonishing adeptness highlights the contradictions, the apparent “heads I win, tails you lose” nature of many common CIO situations. (For example, “You run one of the most pervasive, critical functions, yet you must prove your value constantly.”) But she then goes beyond what could have become a mere litany of complaints (sure, sure, life is tough all over), to fold in specific and insightful case studies where individual CIOs have found ways to transcend and even overcome those dilemmas.

The CIO Paradox concept turns into an addiction once you’ve read the book’s introduction: you start to see them everywhere you look.

Heller apparently honed these concepts for years prior to authoring this book, getting feedback and suggestions from the many CIOs she encountered as a journalist for CIO magazine, then from facilitating “CIO Best Practice Exchange” panels at industry conferences, and finally from her work as an executive recruiter. And the polish shows. What also shows is her abiding fascination and admiration for the CIO role. She writes, “To me, the CIO role is simply fascinating: It is rife with so many contradictions that I cannot imagine how anyone could ever be successful in it. And yet, I meet them every day.”

Heller illustrates, consistently throughout the book, a deep understanding of the key levers of IT, an understanding that is surprisingly rare even among many industry pundits. Many of her sections and conclusions map closely to what I’ve covered in this blog over the past few years. Here are just a few nuggets that particularly resonated with me:

  • “Operations management is the price of entry to the CIO position”;
  • “If you have not found a way to convince your stakeholders that foundational investments are the table stakes of apps and business intelligence and innovation, you will get crushed between the Scylla and Charybdis of legacy technologies and business demand”;
  • “Be accountable. If you say you’re going to do something you need to do it. That is the only way to build trust and respect”;
  • “IT is more about technology than it has been for decades…. Today, it is all about the business and it is all about technology.”

A minor quibble: not surprisingly, a few of the sections (for example, the one on enterprise architecture) tend to exhibit a recruiter’s perspective. Personally, I found the chapters on recruiting, CIO career path, and CIO board membership, while interesting and useful, to be somewhat out of place and less “on theme” in comparison to the others. Heller no doubt had her own “damned if you do, damned if you don’t” dilemma on including these; as a seasoned recruiter of CIOs and IT personnel, she clearly has significant experience and useful observations to share on these matters, even if they don’t fit quite as smoothly into the “CIO Paradox” unifying theme.

Readers of my other reviews know that I tend to look askance at books on CIO matters that just propose easy solutions, and that I look instead for books that pull aside the curtain on the complexity and tradeoffs that are common in our roles. Heller’s very theme, the CIO Paradox, is a poster child example of such a nuanced approach. In fact, the CIO Paradox concept turns into an addiction once you’ve read the book’s introduction: you start to see them everywhere you look in the IT spectrum of activity. Heller doesn’t give pat answers (actually, she cautions in the introduction that this is not a step-by-step guide), but she instead provides numerous tips and case studies that illustrate a few (sometimes divergent) ways in which real-life CIOs have grappled with (and transcended) the paradoxes she’s describing.

Reading the book, I was frequently reminded of the famous F. Scott Fitzgerald quote: “The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function.” Heller’s intelligence on CIO matters is clearly first-rate, and she heightens ours as well in this book.

One end paradox of the book: it struck me that the people who most need to read it aren’t the CIOs at all, but the CEOs, the COOs, and other C-level peers. For those are the roles who often least understand the “dual-edged sword” nature of the CIO role. It’d be nice to see the “aha” light go on in their eyes too.


  1. Peter, your review is spot on. When The CIO Paradox was in the works I admired Martha’s passion in her research. At the same time I wondered did we really need another CIO book. I bought the book when it came out purely based on my love of Martha’s journalism style and enjoyment of her CIO Inc columns and newsletters. I was not disappointed! It is the most readable, practical and holistically insightful CIO leadership book ever! I love it and tell every CIO and CIO want to be to read it. Thank you martha and thank you Peter for spreading the word.

  2. Thanks, Mary. The only thing I’d add is that I suspect we’ll always “need another CIO book.” There’s so much to say about the role, its definition, its metamorphoses, its recalibrations, and all of that needs to be constantly reevaluated and/or changed as the world around us changes. As is the case with Martha’s own observation about the CIO role, that very variety (and constantly new perspectives) is what fascinates me the most.

  3. Peter, thanks for sharing. I’ll take a look at it.

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