How I Approach Technology Upgrades After Acquiring a Business

When I buy a business, I know one of the first questions I’ll face is whether the technology stack needs to be upgraded. For many small businesses, technology has been neglected. Owners focus on survival and serving customers, not on modernizing software, hardware, or systems. That means I often inherit outdated tools, inefficient processes, and hidden risks.

Over time, I’ve learned that how I approach technology upgrades after an acquisition can determine whether the business scales smoothly or gets bogged down. The wrong approach, like rushing upgrades or forcing unnecessary changes, can alienate employees and waste money. The right approach, thoughtful, staged, and focused on ROI, can unlock efficiency and position the company for growth.

Why Technology Upgrades Matter

Technology upgrades matter because they impact:

• Efficiency: Outdated systems slow employees and create errors.
• Data visibility: Modern systems provide better reporting for decision-making.
• Customer experience: Customers expect seamless digital interactions.
• Security: Old systems are vulnerable to breaches.
• Scalability: Growth requires systems that can handle volume.

I don’t view technology as optional; it’s infrastructure.

My Early Mistakes

In one of my first acquisitions, I rushed to implement a new CRM system. Employees were overwhelmed, adoption was poor, and productivity dropped. In another deal, I underestimated the cost of replacing outdated hardware. The expense hit cash flow harder than expected.

These mistakes taught me that technology upgrades must be phased, measured, and tied to business outcomes.

How I Evaluate Technology in Diligence

During due diligence, I ask:

• What software and hardware systems are currently used?
• How old are they, and what are the licensing costs?
• Are systems integrated or siloed?
• What complaints do employees have about technology?
• Are there security vulnerabilities?

The answers tell me how much upgrading will be necessary.

My Framework for Technology Upgrades

When I take over a company, I follow a step-by-step framework:

1. Listen First
I ask employees what frustrates them about current systems. This prevents me from solving the wrong problems.

2. Stabilize Critical Systems
If there are urgent risks like unsupported software or security gaps, I fix those first.

3. Prioritize High ROI Upgrades
I focus on changes that quickly improve efficiency or customer experience.

4. Phase Implementation
I introduce upgrades in stages, giving employees time to adapt.

5. Train and Support
I invest in training to ensure adoption.

6. Measure Impact
I track metrics like productivity, error rates, and customer satisfaction to confirm value.

Why Technology Impacts Valuation

Businesses with modern systems are worth more because they’re scalable and less risky. Companies with outdated technology often require lower valuations due to the cost of upgrades.

Final Thoughts

I’ve learned that technology upgrades are one of the most important parts of post-acquisition strategy. Done right, they unlock growth. Done wrong, they create chaos. That’s why I evaluate systems carefully, prioritize upgrades by ROI, and implement changes thoughtfully.

I continue sharing my acquisition playbook and strategies at DrConnorRobertson.com, where I document how I turn outdated businesses into scalable operations.