Something is broken, something is urgent, and a salesperson shows up with a solution that sounds like relief.
That’s usually where things go sideways.
Getting burned by vendors isn’t about being naïve. It’s about being under pressure. Decisions are made quickly, with partial information, and the downside doesn’t show up until months or years later. By then, the contract is signed, the data is locked in, and leaving feels harder than staying.
The way out of that cycle isn’t better sales resistance. It’s better structure.
Before looking at features or pricing, there are a few questions that matter more than anything else.
The first is ownership. Who owns the data, and how hard is it to get it out? If exporting clean, usable data feels like an afterthought, that’s a warning sign. Vendors who make it easy to get in but hard to leave are betting on lock-in, not value.
The second is integration. Not whether the vendor claims to integrate, but how. Does the data move automatically? Is it one-way or two-way? What breaks if something changes? “We integrate with everything” usually means “you’ll be stitching this together yourself.”
The third is incentives. Vendors are optimized to sell, not to live with the consequences of their software inside your business. Long contracts, financing, and bundled pricing all shift risk onto the owner. That doesn’t make them evil, but it does mean you have to be deliberate.
A good vendor will answer uncomfortable questions clearly. A bad one will deflect, minimize, or rush you past them.
The goal isn’t to find perfect software. It’s to avoid traps. To choose tools that can evolve as the business does, without forcing you into a corner. To make sure today’s solution doesn’t become tomorrow’s constraint.
This is where having a walkthrough matters.
When you slow down and evaluate vendors against the same criteria — data flow, integration, ownership, exit paths — patterns become obvious very quickly. The noise falls away. You stop reacting to pitches and start making decisions that fit your business.
If you want help walking through it, that’s what I do. Not selling software. Not pushing platforms. Just helping business owners evaluate options, set things up correctly, and own the result so they don’t have to think about it again.
You shouldn’t have to learn this the hard way. And you shouldn’t have to fight your tools to keep your business running.
If you’ve been burned before, you’re not alone. And you don’t have to repeat it.
If this speaks to you, reach out. I’ll roll up my sleeves and share my expertise.