I’m Joe Schiavone. I am a principal analyst here at Forrester. My experience has afforded me the opportunity to learn from some amazing leaders while developing my own style along the way. I have been leading tech for global organizations from P/E-backed and startups to large global companies. My comparative advantage, and what has led to my success, has been my disciplined approach to strategy and M&A.

Over the years, I have had to make high-impact, high-visibility decisions, pivoting on roadmaps where pivoting wasn’t an option and leading teams to see past the finish line.

I have learned that being practical and direct is the best approach, that teams are only as strong as their weakest links, and that having those hard discussions that might feel uncomfortable tend to yield the greatest results.

A Three-Year Roadmap … How About Three Months?

As we all know, a solid roadmap with a shiny North Star that we skillfully put in reach stays on track for a few months. Priorities change, QBRs happen, some sort of incident occurs, and funding shifts elsewhere.

This is when you realize that the long-range plan and future state of your architecture, the value you hope to create with your organization, all of which you pragmatically planned, has now come to a halt regardless of the efforts you and your team have put in.

Tech leaders are responsible for delivering results and they need to architect what I will refer to as modular roadmaps. Grouping buckets that if they stop one the rest must stop, a hierarchy of dependencies that all have a value assigned. They need to be able to validate the impacts of pivots the org imposes on us.

Life Lesson

All roadmaps change, especially the further they go out. Funding changes, earnings get missed and now that $50 million you had for the next three years is looking more like $14 million, and you’ve already spent half.

I speak from experience.

I was with a global manufacturing firm. We had no manufacturing execution system (MES), none of our production lines were talking to each other, and we had enormous amounts of data that needed to move through our legacy (and by legacy, I mean archaic) infrastructure.

Lightbulbs go off, with a full infrastructure refresh globally spanning more than 30 locations. Bring in an MES, scanners, new switches, stronger circuits, all future-proofed (for at least three years to end of life) — you get the idea.

Architects design everything, we spin up POCs, funding gets approved, licensing contracts are signed, and we are off to the races …

Six Weeks Later … (Squidward Voice)

Some of our IP is leaked on the internet. It was like a referee jumped in and called the game because of lightning. Everything stopped. Initiative 1A became the only thing that was funded: security. If it didn’t impact security, it was not moving and, to restate, not funded.

So great, let’s look at new cameras with AI and capabilities that were once only seen in the movies. We bring in several vendors, impressive POCs, amazing quality cameras, etc. We start digging — where does the footage get stored, how are they powered, what is the required density — the list goes on and on.

So remember that refresh from six weeks earlier, where all the bills of material were created and we took delivery? Well, now we need POE++ to power the cameras (not in the plan), the planned AP density was great but not sufficient when these cameras were to come online; we had to consider storage; and we moved a lot to the cloud. Cloud = latency; now we needed local VMS solutions, plus alerting, etc. As you can imagine, without getting into all the details, this disrupted everything from the vendor pulling cables to the overall architecture that was designed. My teams were flustered. Dependencies became bottlenecks. Governance slowed decision-making. Friction built up, and momentum slowed — let’s be honest, it came to a halt. Morale was fading.

My lesson: Build in flexibility and in some cases a cooling off period post roadmap. Ultimately, we pivoted, moved hardware to a greenfield that didn’t need sophisticated cameras, and refreshed other sites that were not as impacted. We turned a two-thirds refresh into a full refresh by pivoting on the gear we already procured.

So what does this have to do with strategy and roadmaps? Roadmaps aren’t scalable. They are restrictive, and CIOs need to focus on modular adaptability.

Why Have A Roadmap?

We all need something to plan for! Tech leaders, you all participate in those unusually long budget meetings where you move pieces around like doing a puzzle trying to find the next piece, right?

Roadmaps help give us a perfect-state future view that will always evolve as we see the goalposts continue to move further.

Another important aspect is that not all areas will move and change at once and not all pivots are detrimental to the plan, so keep creating those roadmaps; just make sure you can move a piece of that puzzle, at times to a completely different puzzle.

My Perspective

    • Many technology strategies break down during change, not during design.
    • Choices that cannot be acted on simply postpone the point where trade-offs become unavoidable.
    • What is labeled as technical debt often reflects decisions that were deferred or avoided when action was still possible.
    • Speed depends as much on decision systems as on technology, including who has authority, how quickly decisions are made, and how clear those decisions are.
    • The CIO’s role centers less on creating a flawless strategy and more on shaping an organization that can adapt when conditions are imperfect.

Here’s a question I have started asking my leaders that you might want to ask yourself:

If your top priority changed tomorrow, how much of your current roadmap becomes obsolete — and how long would it take you and your teams to realign?

    • Look at your contracts and where they quietly lock in cost, scope, or timelines that are hard to reverse once priorities shift.
    • Look at your dependencies and how much work, coordination, or negotiation it would take to change direction without breaking things.
    • Look at how decisions really get made day to day, not the org chart version but who has to agree before anything actually moves.
    • Look at how long it takes for a priority set somewhere else to reach you in a way that changes plans already underway.
    • Look at how much of that lag comes from built-in structures like governance, funding cycles, or approval paths rather than one-off issues.

Those answers will tell you volumes about the resilience of your strategy.

Why This Matters Now

CIOs are operating in environments where yesterday’s plan can quickly become today’s liability.

    • AI is compressing timelines.
    • Business models are shifting faster than ever.
    • Decision windows are shrinking.

Gaps are widening between reality and expectations, friction is turning into cost, delay is creating unmitigated risk, and rigidity becomes your worst enemy.

The CIO’s Evolving Role

When I think about the role of the CIO today, I don’t see it as the owner of technology. I see it as the designer of an organization’s ability to adapt and change.

That means focusing on more than systems:

    • Decision rights: Who can make decisions, and how quickly?
    • Governance models: Do your guardrails enable movement?
    • Talent structures: Are teams empowered to act?
    • Investment flexibility: Can resources shift when priorities change?
    • Execution discipline: Is your organization prepared to pivot without losing momentum?

Because in the end, strategy is only as strong as the system that must carry it out.

My Point of View

“Most tech organizations fail at strategy because they confuse having a plan with having the ability to change it. The failure shows up when commitments harden, decisions slow, and your organization discovers that it designed for certainty where adaptability was required.”

The Takeaway

If your strategy assumes stability, it’s already at risk. The true differentiator is how quickly your organization can adapt without losing momentum, instead of how perfectly laid your original plan was. High-performance IT is what drives us, but adaptability is what builds confidence, helping leaders face uncertainty, embrace challenges, and move forward with clarity and resilience.

Your role is shifting from defining direction to enabling change at speed. To succeed, you’ll need to rethink architecture, governance, and operating models as one cohesive system.

Design for change now — or manage disruption later.

I Want To Hear From You

Is your current strategy a fixed monument or a composable platform designed to handle whatever comes next?

I welcome your perspective. Drop a comment below or connect with me via email: jschiavone@forrester.com.