5 Questions Vendors Won't Like (But Your Business Needs Answered)

Software vendors are good at saying yes. They're very good at it. They'll say yes to almost anything if it gets you to sign.

The problem is that "yes" at the beginning often becomes "that's not included in your plan" or "that requires custom development" or "actually, that's not how the system works" once you're live and dependent on them.

The Five Questions

1. "Can you show me a business like ours that successfully integrated this system with our ERP?"

Watch what happens when you ask this. The vendor will often go quiet. They'll talk about the capability to integrate with your ERP. But they won't name a customer who actually did it.

This tells you everything. If they can't point to a real example in a real business like yours, the integration probably required so much customization that it's not a repeatable process. And that means you're paying for a one-off, expensive project—not buying a plug-and-play feature.

2. "What happens to my data if I leave?"

Can you get your data out in a standard format? Can you take your customer information, order history, and financial data and move it to another system?

Many vendors want to make this very difficult (so you never leave). They'll say things like "we can export it as a CSV in 6 weeks" or "there's a migration fee" or "some data isn't extractable."

If they're cagey about this, it means they've built a lock-in. And lock-in always costs money eventually.

3. "If I hit a problem that your support team can't solve in two weeks, what's my option?"

You're going to have problems. That's not an if, it's a when. The question is: what can you do when the vendor's support team is stumped?

Can you hire a third-party consultant? Can you access the source code if you need custom fixes? Or are you completely dependent on the vendor's timeline?

If you're completely dependent, you've just handed over control of your business operations. That's a risk.

4. "How much will the implementation cost, and what happens if we go over budget or timeline?"

The vendor will give you a quote. They'll also tell you it's an estimate. What they won't tell you upfront is what happens if you go over.

If the quote is £20k and you end up at £40k because of unexpected customizations, who pays for it? Is there a cap? Is there a "time and materials" escalation clause buried in the contract?

Get this in writing before you sign anything. And ask specifically: "What is the trigger for additional costs?" Most of the time, the answer is "scope creep"—which means you asked for something slightly different than what was originally quoted, and now you're paying for it.

5. "Can you show me the contract for someone else who did a similar implementation?"

This is bold. But vendors know other vendors. They've done this before. They can almost certainly show you a reference contract.

Why do this? Because contracts are where vendors hide things. The sales person will tell you one thing. But the contract will have escape clauses, liability caps, and terms that contradict what you were told.

Seeing a real contract—even anonymized—tells you what you're actually signing up for. And you can ask your solicitor to review it before you commit.

What These Questions Do

These five questions separate vendors who are confident in their product from vendors who are confident in their sales pitch.

A good vendor will answer these clearly. They'll give you examples. They'll talk about risks honestly. They'll put things in writing.

A vendor who won't answer these questions, or who gives vague answers, or who says "that's a great question for the implementation team," is telling you that they're not confident. And that's worth knowing before you sign a three-year contract.

The Bottom Line

Vendors don't like these questions because they force specificity. They prefer to stay at the level of "we can do that" rather than "here's how we did it for someone just like you, and here's what it cost."

But specificity is the only thing that protects you. The details are where the problems live. And the vendors who won't give you details are telling you something important about who they are.