The Myth of Proactive IT — And What Actually Gets Organizations to Change

I think most organizations believe they’re being proactive about IT. They invest in tools, they talk about best practices, and they schedule audits. They hold planning meetings about “modernization,” “security,” and “resilience.”

And yet, when real change finally happens, it usually follows a decidedly less orderly occurrence: A breach, a failed audit, a close call, or an outage that reaches the C-suite. I call it crisis-driven transformation.

While we might refer to this as failure, it's not a failure of intent. Rather, it's one of urgency, or more accurately, of a lack thereof.

Why “proactive IT” falls short of change

In theory, proactive IT is simple: identify risks early and address them before they become problems. In practice—in my experience, at least—it rarely works that way. My theory is that risk is too abstract to drive big change. Until, of course, it isn’t.

As long as systems are running and customers aren’t complaining, potential failures feel hypothetical. Security gaps sound academic and technical debt looks tolerable. Competing priorities—revenue, growth, staffing, keeping up with compliance demands—always feel more immediate. IT teams might see the warning signs clearly, but as concerns move up the organization, urgency tends to dissipate. What begins as a serious risk discussion turns into a future consideration. Understanding risk intellectually is not the same as feeling it operationally.

Crisis: the most effective (and worst) change agent

When a crisis hits, everything changes. Budgets get approved, decisions accelerate, and resistance to change seems to melt. A favorite phrase of mine: Debate collapses under the weight of consequences.

From a purely practical standpoint, crisis is incredibly effective. It creates clarity and aligns priorities. But it’s also the most expensive, stressful, and damaging approach to progress. The real problem isn’t that crises drive transformation, it's that for many organizations, they're the only thing that does.

The uncomfortable truth IT leaders already know

Most organizations don’t change just because they are convinced. They change, rather because of fear. That’s not a moral judgment. It’s human nature and organizational psychology at work. The challenge for IT leaders and trusted partners isn’t to deny this reality, but to work with it responsibly. If pain creates urgency, then the real question becomes, "How do we create urgency without the crisis?

Simulating pain without the disaster

Mature organizations don’t wait for reality to teach hard lessons. Instead of hoping that awareness alone will drive change, they make risk tangible and immediate through deliberate exercises and assessments. They rehearse the crises.

That might look like:

• Security assessments framed around real-world business impact, not just technical finding
• Tabletop incident-response exercises that walk leadership through “day one” of a breach
• Architecture reviews that model failure scenarios instead of best-case assumptions
• Audits positioned as decision-making tools, not compliance theater
  
  

Such tactics bring clarity. When leaders can see how a failure unfolds—who is affected, what stops working, what it costs—conversations change and priorities realign. Action becomes a little easier and urgency no longer is at the mercy of misfortune.

Redefining what proactive IT actually means

Proactive IT isn’t about chasing perfection or eliminating every possible risk. That’s neither realistic nor necessary.

Real proactive IT looks more like this:

• making risk visible instead of theoretical
• translating technical concerns into business consequences
• inviting difficult moments of clarity through rehearsal before reality forces it
  
  

It’s not about predicting the future, but when decision-makers actually prepare for it.

Don’t wait for the wake-up call

No organization sets out to learn lessons the hard way. But many do just that simply because they've never managed to develop an effective way to create a sense of urgency sooner.

The goal of proactive IT is to make sure the first real wake-up call isn’t catastrophic. Organizations that understand this recover more quickly when things go wrong.

A better way forward

Crisis-driven transformation works because it strips away ambiguity, forcing organizations to confront reality all at once. Organizations that mature beyond reactive IT learn how to create clarity intentionally. They surface risk early, make consequences visible, and rehearse uncomfortable scenarios before they’re forced to live through them. In doing so, they replace fear with preparedness, and chaos with informed decision-making.

Proactive IT, then, isn’t about optimism or perfection. It’s about discipline. It’s about choosing to confront hard truths on your own terms rather than waiting for circumstances to do it for you. The most effective time to change is before the wake-up call.

Need help deciding your next step? Reach out. I’m ready to help you move forward!