How to Choose Enterprise Software Without Getting Burned

Every company I work with has at least one software purchase they regret.

Sometimes it is a CRM that sales refuses to use. Sometimes it is an ERP implementation that went 300% over budget. Sometimes it is a platform that looked perfect in the demo but cannot handle their actual workflows.

After twenty years of helping companies select and implement enterprise software, I have seen the same mistakes repeated. The good news: they are avoidable.

Why software selection goes wrong

The vendor selection process at most companies looks like this:

1. Someone identifies a need

2. They Google solutions and request demos from three vendors

3. The vendor with the best demo wins

4. Implementation begins

5. Problems emerge

The issue is that demos are performances. Vendors show their software doing exactly what it does best, operated by someone who uses it eight hours a day. Your team will use it differently, with different data, under different constraints.

By the time you discover the gaps, you have already signed a multi-year contract and begun implementation. Switching costs are now enormous. So you make it work, or try to.

A better approach to vendor selection

The companies that make good software decisions do several things differently:

1) They start with requirements, not vendors.

Before looking at any solution, document what you actually need. Not features, but outcomes. What business processes must the software support? What integrations are non-negotiable? What does success look like in 12 months?

This sounds obvious. But most selection processes skip it. They start with "let's see what's out there" instead of "let's define what we need."

2) They involve implementation thinking early.

A tool is only as good as your ability to implement it. Before selecting, ask: Who will configure this? Who will maintain it? What does training look like? What happens when something breaks?

The best software for your needs is not always the best software overall. It is the software you can successfully implement and operate with your current team and constraints.

3) They check references properly.

Every vendor provides references. These are customers who will say nice things. They are nearly useless.

Instead, ask for references at companies similar to yours in size and industry. Ask specific questions: How long did implementation take? What surprised you? What would you do differently? Would you choose this vendor again?

If possible, find customers through your own network who were not hand-selected by the vendor.

4) They test with real scenarios. 

Do not just watch demos. Provide vendors with your actual data and your actual workflows. Ask them to show how their software handles your specific edge cases.

If a vendor cannot or will not do this, that tells you something important.

5) They negotiate before signing.

Enterprise software pricing is almost always negotiable. Discounts of 20-40% are common, especially at quarter-end or year-end. Do not accept the first number.

More importantly, negotiate contract terms. What happens if implementation fails? What are the exit provisions? Who owns your data?

The hidden cost of "free" trials

Many companies think a free trial reduces risk. Sometimes it does. But trials also create momentum toward a decision.

Once you have spent weeks configuring a trial, migrating sample data, and training people on the interface, you have made an emotional and practical investment. Walking away feels like wasting that investment, even if the trial revealed problems.

Be aware of this dynamic. A trial is not a commitment, but it can feel like one.

When to bring in outside help

For small purchases, internal evaluation is usually sufficient. But for enterprise software (the systems your business will run on for the next 5-10 years) independent expertise often pays for itself.

An advisor who has seen dozens of implementations can spot risks you might miss. They know which vendor promises are realistic and which are optimistic. They are not influenced by vendor relationships or internal politics.

I help companies with vendor selection regularly. Not to make the decision for them, but to structure the process, ask the right questions, and avoid the mistakes I have seen too many times.