Technology has become the heartbeat of most businesses. When you buy a company, you are buying its systems, its data, and its technical debt. Yet too many deals still treat technology diligence as a box to tick rather than a discipline to master.

A robust diligence process is more than a checklist. It is an opportunity to see how a business really works under pressure. What technology risks are hidden beneath the surface? How resilient is the architecture? What unspoken dependencies could cripple scaling or integration?

1. Why Traditional Diligence Falls Short

Traditional due diligence often focuses on contracts, licences, and headline systems. But real risk lives in how technology operates every day. Legacy code, unsupported platforms, fragile integrations, and undocumented workarounds can silently undermine a business. These weaknesses rarely show up in data room slides.

Buyers must go deeper: examining source code health, infrastructure resilience, and the culture of the technology team. The question is not just what exists on paper, but what happens when things go wrong.

2. Hidden Costs and Technical Debt

Many acquirers underestimate the cost of modernising outdated technology. Technical debt compounds over years, becoming harder and more expensive to unwind. We have seen deals where technology remediation costs exceeded 30% of the purchase price.

Due diligence must quantify these costs before signing. How many systems are end-of-life? What will it take to integrate platforms? Is there vendor lock-in that limits flexibility?

3. The People Factor

Technology diligence is incomplete without understanding the people who run it. Are there single points of failure? Does institutional knowledge live in a few heads? What happens if critical engineers walk out the door?

Cultural alignment is just as important. If the target’s technology culture is risk-averse or outdated, integrating it into a more modern environment will be harder.

4. Red Flags We Watch For

• Lack of documented architecture.

• Manual processes masquerading as automation.

• Security practices that look good on paper but lack enforcement.

• Overreliance on key individuals.

• No clear roadmap for scaling.

5. What Good Diligence Looks Like

One of the most powerful tools in this process is the value chain diagram. Mapping end-to-end business processes against supporting systems – for example, the entire lead-to-cash lifecycle – quickly exposes gaps, duplication, and brittle integrations. By showing where technology and operations intersect, it becomes clear what needs investment and what can be retained. This visual clarity helps boards understand both the opportunity and the risk before committing to a deal.

Effective technology diligence combines forensic analysis with practical experience. It asks not just, “What is here?” but “Is it fit for purpose, and what will it cost to fix?”

At Relentica, our approach includes:

• Architecture and scalability assessment.

• Security and compliance checks.

• Technical debt quantification.

• Culture and capability evaluation.

• A clear roadmap for integration or remediation.

The Takeaway

M&A success is not just about financial engineering. It’s about knowing what you’re really buying and what it will take to make it work. The most successful acquirers see technology diligence as an investment, not an afterthought.

If you want to protect value and avoid surprises, look beneath the surface. That is where the real risks hide.