Prioritizing legacy system upgrades within budget comes down to impact vs. effort. Start by assessing which systems are the biggest bottlenecks—whether it’s performance, security risks, or maintenance costs. A good way is to use a scoring model, weighing factors like criticality to business operations, compliance risks, and cost of failure. For example, if an outdated payment processing system is slowing transactions and increasing downtime, that’s a clear priority over a rarely used internal reporting tool. Quick wins with high ROI should come first, balancing risk and business value.

I prioritize by assessing their impact on daily operations and customer satisfaction, weighing maintenance costs and risks against upgrade expenses, and targeting quick wins that deliver immediate value.

I’d assess business impact, security risks, and maintenance costs to prioritize upgrades. The most critical and high-risk systems come first, while lower-priority updates can be phased in strategically to stay within budget.