Thornton May
Columnist

Winning over IT value skeptics: CIO job No. 1

Opinion
Aug 26, 20255 mins
Business IT AlignmentIT Leadership

Helping key stakeholders understand the IT value creation process is the key to staving off post-mortems of IT projects gone wrong.

Mature hr manager listen applicant during job interview in office, looking at candidature with skepticism not sure that person is suitable for vacant position, client and bank worker meeting concept
Credit: fizkes / Shutterstock

To succeed, CIOs need to be perceived as value creators. At the beating core of any great IT organization is the ability to deconstruct the various technological components, management processes, and mental models necessary to maximize business value today.

Career realpolitik tells us that deep in the back of the minds of the board of directors, executive peers, and rank-and-file employees is a subliminal, never-ending question of whether every dollar spent on IT generates a positive — let alone multiplying — return.

Still, while just about every actor in the digital economy is an IT value skeptic constantly questioning whether IT is delivering enough benefits, very few actually understand the gastronomy associated with baking the IT Value Pie.

Fifty-plus years into the digital economy and IT value creation remains a mystery to most key stakeholders. And before you think the metaphor is a stretch, perspective-rich, 20-plus-year, award-winning CIOs have told me that IT value creation is all too often like baking a pie. That includes Brian Shield, formerly CIO of the Boston Red Sox, now at Safe-Guard Products International; Mike Coleman, CIO at Phantom Fireworks; Kevin Burns, CIO at the City of Melbourne; Dennis Reiman, formerly CIO at Southern Connecticut State University; and Cheryl Smith, formerly CIO at McKesson.

According to these IT leadership gurus, you often have to put something in the oven and then peek inside to see how your pie looks. Getting a full-value IT pie out of the oven is not guaranteed.

Flipping the script on conversations about IT

Organizations that consistently deliver on the promise of IT have taken steps to eliminate much of the mystery associated in IT value baking. They are attempting a “no translation” form of technology management wherein tech spending is understood in the context of how it impacts quality of work, life, and bottom and top lines.

Step One involves having conversations with key stakeholders to help them understand the totality of the IT value creation process. When was the last time you sat in on a deep, free-ranging discussion about where IT value comes from? No doubt you’ve been involved in more emotional post-mortems of IT projects gone wrong than you’d prefer.

It would be fascinating to have the various AI tools floating around the economy do a semantic analysis of the totality of IT conversations in any given organization. One would probably find a significant percentage of conversations associated with finger-pointing, accountability avoidance, and “could’ve/should’ves.”

What percentage of IT conversations in your organization explicitly detail the ingredients of IT value creation and the processes associated with combining those ingredients to actually deliver value?

The IT supplier equation

Step Two of winning over IT value skeptics involves IT agency — that is, the capacity of an individual to act independently and make their own free choices. An individual is thought to have agency when they feel they are the one in control, rather than being controlled by external forces or circumstances. 

In an ideal world, IT agency features an economic actor — a CEO, COO, or CMO — setting forth a measurable objective or outcome. Optimally, the IT organization thereupon comes up with a set of strategies, programs, and budgets detailing how best to achieve that objective or outcome utilizing the technology portfolio available. I am not certain that anyone on the demand side of the IT value exercise feels they are in control. I am specifically concerned that we may have ceded too much authority to IT suppliers.

In July 2025, there were nine firms with $1 trillion market capitalizations. Eight of them are tech companies. Conclusion being: Tech suppliers, particularly AI tech suppliers, are booming. The question IT value skeptics should be asking is, How much value is being captured by the demand side of the technology economy?

I am reminded of Fred Schwed Jr.’s investment classic Where Are the Customers’ Yachts (1940). A visitor to New York observing all the yachts belonging to stockbrokers and investment advisors naively asked, “Where are the customers’ yachts?” The point of the book being there is far more money in providing financial advice than there is in receiving financial advice. Is the IT analog that there is much more money/value associated in supplying technology than there is in applying technology?

Are your suppliers universally perceived as adding value to the enterprise versus extracting value from it? Does every IT supplier contract require an accounting of benefits delivered before final payment is rendered?

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