Eleven questions a dealer principal should ask any software vendor

A software demo is a performance. Everything you are shown works, because the person showing it chose what to show. The useful questions are the ones about failure, ownership and exit.

On what it actually does

1. 01Show me a real conversation this had with a real customer, end to end, including one that went badly.
2. 02What is it structurally incapable of saying? Not discouraged from — incapable of. Ask specifically about quoting a rate and claiming an approval.
3. 03What happens when one of my salespeople replies in the middle of a thread the system is working?
4. 04If a customer says stop texting me in their own words rather than the keyword, what happens?

On failure

1. 01What happens when my inventory feed returns half the units it should? Walk me through it.
2. 02When was your last outage, how long was it, and what did your customers see?
3. 03If this claims an appointment that the customer never agreed to, what caused that and what prevents it?

A vendor who cannot describe a specific failure has either never had one, which is impossible, or is not going to tell you about the next one either.

On ownership

1. 01Who owns my customer data, in writing, and what happens to it if I leave?
2. 02Can another store on this platform see my leads? Prove it is enforced below the interface, not by a screen filter.
3. 03Can I export everything — leads, conversations, documents — myself, today, without asking you?
4. 04If I sell a rooftop, how do I separate its data cleanly?

The one that tells you the most

Ask them what their product deliberately does not do, and why.

A vendor with a real product has a list, and the reasons are specific — we will not post to a public marketplace without a person pressing the button, we will not quote a rate, we will not text an old database without a manual release. A vendor whose answer is that it does everything is telling you they have not thought about the edges, and the edges are where you will get hurt.