Solutions for Your Problems, or Problems for Their Solutions?

I've spent a long career on both sides of the vendor table. I've bought software and services, and I've sold them. Over that time I've come to think one question sorts vendors more reliably than any feature list or price comparison: is this vendor selling me a solution to my problem, or selling me a problem that happens to fit their solution?

The two can look almost identical in a sales meeting. Both vendors are friendly and both have good slides. Both will tell you they understand your business. The difference is the direction the conversation runs. One starts with what's actually going wrong for you and works toward whatever fixes it, even if that isn't much. The other starts with what they sell and works backward until your business seems to need it.

Most vendors aren't doing this on purpose. If you sell a hammer all day, every conversation starts to sound like a nail. Sales teams have targets, product teams ship features that need customers, and a new capability everyone is talking about gets added to every pitch whether it fits or not. None of that makes anyone a bad actor. It does mean the job of noticing falls on you, the buyer.

What working backward sounds like

The first sign is usually how fast the demo starts. If you're seeing the product before anyone has asked what's going wrong, the vendor has already decided what your problem is. A discovery call that turns into a tour within the first ten minutes is a demo with a few questions attached.

The second sign is vocabulary. Listen to how your problem gets described back to you. If you said "we keep losing track of who we're supposed to follow up with" and it comes back as "you need pipeline visibility and lead-scoring automation," your problem has been translated into their product's terms. Sometimes that translation is accurate. Often it quietly makes the problem bigger, so it matches the size of the solution.

The third is that every problem maps to a feature. A vendor who has an answer for everything you mention, with no "we're not the right fit for that part," is either remarkably well suited to you or not really listening. Real fits have edges.

The fourth is the problem you didn't know you had. Good vendors do sometimes spot something you missed, and that can be valuable. But if most of the meeting is spent convincing you of a problem you'd never noticed, which happens to be the one their premium tier solves, it's worth slowing down and asking whether it's costing you anything today.

What starting from your problem sounds like

The vendors worth working with tend to ask a lot before they show anything. They want to know what you've already tried, what it costs you when things go wrong, and what "fixed" would look like. They describe your problem back in words you'd actually use.

They're also willing to tell you where they stop. "We don't do that part, and here's who does" is one of the most trustworthy sentences a vendor can say. So is "you probably don't need our bigger plan yet," or even "honestly, a spreadsheet would handle this for now." A vendor who will talk you down from a sale is a vendor whose yes means something.

And they're clear about what leaving looks like. Who owns your data, how you'd get it out, and what you'd be left with if you walked away in a year. A vendor confident in their value doesn't need the answer to be complicated.

Questions worth asking before you sign

You don't need to be cynical to protect yourself. A few plain questions usually show which direction a vendor is working from.

Ask what problem they think you have, in one sentence, before they show you anything. If their answer sounds like their product's tagline, you've learned something.

Ask who their product is not a good fit for. A vendor who can't answer hasn't thought about it, or doesn't want you to.

Ask what the smallest version of this would be. What's the least you could buy, or the least you could change, and still fix the thing that's actually bothering you?

Ask what happens if you leave. Where does your information go, and what do you keep?

And ask yourself one question after the meeting: did I come away understanding my own problem better, or just their product?

The same question, pointed the other way

There's an uncomfortable flip side to all of this.

If you sell anything, a service, a product, your own expertise, your customers are quietly asking the same question about you. It's easy to fall in love with what you've built and start seeing every conversation as a reason someone needs it.

I try to hold myself to the same test I'd hold a vendor to. Listen first. Describe the problem in the client's words, not mine. Say plainly what I don't do, and when the honest answer is "you don't need me yet," say that too.

The vendors I've trusted most over the years weren't always the cheapest or the most impressive. They were the ones who seemed more interested in my problem than in their pitch. That's a high bar, and it's the right one, for the people we buy from and for ourselves.

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