The lazy CIO’s guide to better IT investment

If you’re like most CIOs, you’re under pressure to introduce exciting new technological capabilities to the enterprise at large, promoting visions of digital transformation, generative AI, AGI, AI transformation, agentic AI, or some other version of being an FBC CIO — that’s “Fully Buzzword Compliant” for those who haven’t joined the AFC (“Acronymic Fan Club”).

You’re under this pressure unless you’ve given up and relinquished responsibility for formulating the organization’s technology vision to a chief digital officer, chief technology officer, or some other titled individual whose job is to make promises you as CIO are supposed to keep.

Don’t do that.

‘Best practices’ vs. basic competence

It’s time for a Venn Diagram. More specifically, it’s time to ask yourself how confident you are of your organization’s third-circle capabilities.

But first, you might be asking, what are Circles #1 and #2?

Good question. They are, respectively, your organization’s ability to implement AI (Circle #1) and digital (Circle #2) capabilities. You are, undoubtedly, reading the pundit-class’s opinions about how important it is for CIOs to be bringing these in, with or without a CTO or CDO, and making them happen.

Before you, as CIO, get too worked up about Venn Circles #1 and #2, though, take a few minutes to ponder Venn Circle #3. That’s the circle that encompasses “best practices.”

Which aren’t best practices at all. Far from it, what’s deemed “best practice” is usually little more than the minimum standard of basic professionalism.

“Best practice” is an irritating example of arguing by assertion. Most often, those who are fond of asserting them aren’t promoting anything particularly onerous. Nor are they promoting practices that can’t be improved upon — what the phrase ought to mean.

“Basic competence” would be a synonym. CIOs should invest in it heavily.

Get lazy

But where, exactly? Here are two ways to figure it out.

One approach would be to create an IT capabilities map, develop data-driven scoring metrics, populating a dashboard, and using the result to construct an IT organizational transformation roadmap. You can certainly do this. At a rough guess the CIO of an average-size enterprise, following this methodology, would be ready to launch sometime in 2026.

Except that they wouldn’t, as they’d have been tossed onto the Career Is Over pile long before the roadmap was ready for approval.

The lazy CIO’s approach probably makes more sense. It follows the hardworking consultant’s approach for such things: have conversations with as many staff members and stakeholders as possible.

In this case, use the Discretionary Dollar framework to frame up these conversations, starting with these three questions:

1. “After spending everything we need to spend we’ll have one dollar left over — a discretionary dollar. What should we spend it on?”
2. “We don’t and won’t have any discretionary dollars. What does that prevent us from investing in that we should be investing in?”
3. “Where have we been spending that we could stop, to turn those dollars into discretionary dollars?”
4. “What else do I need to know about how we’re doing things that makes the IT organization less effective than we need it to be?”

Okay, that’s four questions. So sue me.

For the purposes of your Venn Diagram, toss out everything that fits into Venn Circles #1 and #2. What’s left should, for the most part, fit nicely into Venn Circle #3, namely, where your IT organization hasn’t achieved the minimum standards of basic professionalism.

It might be an unrationalized applications portfolio. Or maybe you’re well down the road to a cloud migration but haven’t applied your Ops team’s ITIL expertise to it.

Or your teams just aren’t as good at project management as they need to be.

But one way or another you’ve discovered ways your organization could be doing a better job of Venn Circles #1 and #2.

Reframe the conversation

That’s when it’s time for you as CIO to have a tough conversation with the Powers That Be about the IT budget. What will make the conversation so tough? Script it and you’ll see:

You: “The IT organization I lead isn’t as effective as it needs to be. To fix the challenges we face we’ll need a bigger budget.”

CEO: “You’re asking me to reward you for underperforming. Tell me how this makes any sense.”

Now that you’ve scripted it you know what you’ll need to do to prepare for the tough conversation: meet one-on-one with the most influential managers and executives in the company and get them on your side of the issue, so they’ll testify on your behalf that the insufficient effectiveness IT faces is underinvestment, not bad management.

And that the cost of underinvestment is getting in the way of achieving Venn Circles #1 and #2.