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When ROI collides with grokking, grokking wins every time

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For all its ambiguity and grammatical misclassification, “digital” as a noun … or “Digital” as a proper noun … has proven more durable than most of the management fads that preceded it.

It isn’t that digital businesses out-perform non-Digital (Analog?) competitors. The fact of the matter is, the definition of “Digital business” varies by commentator, while the definition of “successful Digital business strategy” often fails even such well known logical requirements as not equating correlation and causation.

Speaking of logical analysis, the situation is far worse than even that. As evidence:

According to the definitive source of such things, the Standish Group reports that only about 30 percent of all software projects are successful.

Meanwhile, the often-IT-illiterate Harvard Business Review reports that 70 to 95 percent of all digital transformations fail. Take into account that transformations of any kind are achieved with strategic programs, which in turn are composed of tactical initiatives, which in their turn are accomplished by the collective success of the multiple projects they charter, and you’ll conclude that Digital failures are an example of Sturgeon’s Law: 70 percent of Digital transformations fail because 70 percent of everything a company tries fails.

What’s made Digital as business strategy so durable is (in my awesomely humble opinion) that it has legitimized the pursuit of revenue as a strategic objective, making it more desirable than cutting costs. And, it is rooted in the proposition that information technology can provide a powerful path to more, and more profitable revenue.

In addition, Digital, along with IT’s successful employee-virtualization-response to COVID-19, turned the executive suite’s perception of IT from “where projects go to die,” to “the most important business function in the enterprise.”

Another factor in Digital’s executive suite staying power wasn’t something anyone would have predicted a decade or so ago: Unlike previous IT-driven requests for capital investment, by the time “digital” had acquired its capital D and had been turned into a noun, business executives had adopted Blackberries and loved them, right until they discarded them for smartphones accompanied by a wide variety of handy apps.

Add to that their unavoidable experience shopping for merchandise on and, for many, shopping for Kindle books there too, and strategy discussions didn’t have to start with “here’s what a smart product is” explained to skeptical executives reacting with thousand-yard stares. They started with “how can we make our products and services smarter?”

Bob’s last word: Some 60+ years ago, in his revolutionary Stranger in a Strange Land, Robert Heinlein introduced us all to the word “grok,” meaning to understand something deep in one’s kishkes (I’m paraphrasing).

Last week I wrote about ROI and its flaws, concluding that ROI’s utility is limited when it comes to writing successful project proposals, not to mention evaluating them.

At the same time, what’s been badly underemphasized when it hasn’t been ignored completely is how important it is to write proposals your company executives and governance councils can grok.

That’s because having to convince someone of something they already grok is a lot like having to persuade them that the tall green thing they’re looking at through their window is a tree.

Bob’s sales pitch: Looking for someone to keynote an event? After publishing a dozen or so books and some 1,800 or so columns, it’s safe to say I have a strongly held opinion about just about any subject you can name.

I’ll be happy to share a few of them from your podium.

Think of it this way: You’ll be choosing someone to give the keynote. Why not yours truly?

Now on’s CIO Survival Guide: Why IT communications fail to communicate.” The point? Our tendency to use documentation to communicate, instead of recognizing that its role is to remind everyone of what they’ve already communicated.