I've sat through more software demonstrations than I can remember. Most were impressive. The dashboards looked beautiful. The automation was compelling. The sales presentation answered every question... except the ones that mattered most.
Over the years, I've learned that the quality of a software decision is determined long before the contract is signed. It comes down to asking the right questions. Here are the three I always recommend.
1. What business problem are we actually trying to solve?
This sounds obvious, but it's surprising how often organizations begin evaluating software before clearly defining the problem. Software should solve a business problem. It should not become the business objective. If your team cannot describe the problem in one or two clear sentences, you're probably evaluating products too early.
2. What happens if we do nothing?
Every purchase has an opportunity cost. Sometimes the current process is inefficient enough that change is essential. Other times, the problem is merely inconvenient. Understanding the cost of doing nothing helps determine whether the investment is urgent, important, or simply nice to have. The answer often changes the buying decision.
3. How difficult will this be to adopt?
This is the question organizations ask far too late. Buying software is easy. Changing how people work is hard. The best solution on paper often fails because users don't embrace it, training takes longer than expected, or business processes weren't ready to change. Technology creates value only when people actually use it. That's why adoption deserves as much attention as features.
One Final Thought
Software vendors sell products. That's their job. Your job is to make the best business decision for your organization. Those aren't always the same thing. The most successful technology leaders I've worked with weren't the ones who bought the most software. They were the ones who asked better questions before they signed the contract.
At Solutioneering, we help organizations evaluate technology through a business lens, reduce implementation risk, and make decisions that deliver long-term value. Because the most expensive software purchase is often the one you didn't need to make.