The Hidden Gifts and Surprises of IT Due Diligence in Acquisitions

Acquisitions tend to arrive wrapped in optimism. Growth. Synergy. Opportunity. New markets. New capabilities. On paper, everything looks clean and exciting, especially during end-of-year conversations when leadership is already in a forward-looking mindset. But anyone who has been through an acquisition from the IT or security side knows the truth... the real story doesn’t begin until the wrapping paper comes off.

IT due diligence is where reality shows up. And like the holidays, some surprises are welcome… while others make you quietly wonder how this ever made it under the tree in the first place.

The Role IT Is Often Asked to Play...

In many acquisitions, IT and security are brought in late in the process. Financials are reviewed. Legal risks are assessed. Market positioning is debated. And then, often close to the finish line, someone asks, “Can IT take a quick look and let us know if anything jumps out?”

That framing alone should raise concern.

IT due diligence is not about a quick look. It’s about understanding what you are inheriting... technically, operationally, culturally, and from a risk perspective. When that work is rushed or minimized, organizations don’t avoid risk; they simply defer it. And deferred risk has a way of showing up at the worst possible time, usually after Day One.

What IT Due Diligence Is Supposed to Cover...

At a high level, most leaders expect IT due diligence to examine:

• Infrastructure and hosting models

• Network architecture and connectivity

• Applications and platforms

• Security tooling and controls

• Data ownership and classification

• Contracts, licensing, and vendor dependencies

• Integration complexity and effort

On paper, that looks straightforward. In reality, those categories rarely tell the full story. Because what matters most isn’t just what systems exist, it’s how they’re run.

The “Surprises” That Almost Always Appear...

Every acquisition has them. They’re rarely malicious, and they’re often invisible until someone starts asking the right questions.

Common examples include:

• End-of-life systems still supporting critical business functions

• Security tools deployed but not actively monitored

• Overlapping platforms owned by different teams with unclear accountability

• Minimal documentation and heavy reliance on tribal knowledge

• Shadow IT filling gaps no one wanted to budget for

• Compliance assumptions that don’t hold up under scrutiny

None of these show up clearly in a spreadsheet. Yet each carries real operational and financial impact once integration begins. Some surprises are small and manageable. Others feel like opening a box and realizing the batteries aren’t included... or worse, the device inside no longer works.

The Risks That Don’t Show Up in Technical Assessments...

The most expensive risks in acquisitions are rarely technical alone. They’re operational, cultural, and they’re human.

Examples I’ve seen repeatedly:

• A security team with tools, but no authority

• An IT team stretched thin and accustomed to firefighting

• No clear ownership of monitoring, patching, or incident response

• Alert fatigue mistaken for “normal operations”

• Assumptions that “someone else” was handling a control

These gaps don’t necessarily indicate incompetence. More often, they reflect an organization that grew faster than its governance model. When you acquire a company, you inherit those gaps along with the assets.

Why Timing Matters More Than Depth...

One of the biggest mistakes in IT due diligence is assuming it must be exhaustive to be valuable. It doesn’t. What matters is timing and intent.

For me, effective IT due diligence focuses on answering a few critical questions early:

• Where are the highest operational risks?

• What must be stabilized immediately after close?

• What assumptions are we making that need validation?

• What risks are acceptable short-term versus long-term?

This allows leadership to make informed decisions rather than optimistic ones. The goal isn’t to delay an acquisition, it’s to prevent preventable surprises from derailing it.

How to Scope IT Due Diligence the Right Way...

Well-scoped IT due diligence isn’t about creating fear. It’s about creating clarity. Some guiding principles that I feel consistently work:

Bring IT and Security in Early

Not to block the deal, but to frame risk honestly.

Ask How, Not Just What

“How do you monitor this?” matters more than “Do you have it?”

Validate Assumptions

If something is described as “covered,” ask who owns it and how it’s verified.

Separate Ownership from Accountability

Tools without accountability don’t reduce risk.

Define Day-One vs Day-Ninety Risk

Not everything must be fixed immediately, but everything should be known.

I truly believe this approach respects the business while protecting it.

Why I Believe This Matters More Today Than Ever...

Modern environments are more complex than they’ve ever been. Hybrid infrastructure. Cloud sprawl. SaaS dependencies. Security tooling layered over legacy processes. Add AI-driven automation and increasing regulatory scrutiny, and the margin for error gets smaller, not larger. In this environment, inherited risk compounds quickly. The organizations that handle acquisitions well aren’t the ones with the most tools. They’re the ones with the clearest understanding of their operating reality.

Acquisitions can absolutely be gifts. They can accelerate growth, expand capability, and create real value. But only if leadership takes the time to unwrap them carefully. IT due diligence isn’t about pessimism. It’s about stewardship, of systems, of people, and of trust. When done well, it prevents surprises from becoming problems and allows teams to start the new chapter with eyes wide open.

And that’s a much better way to start the new year than discovering what was hidden beneath the wrapping paper.