Software demos are designed to show you the best 20 minutes of a product. These questions are designed to show you the other five years. Ask all fifteen, write the answers down, and make the vendor put the important ones in the contract.
Money
- 1. What is the all-in first-year cost? Licenses, implementation, training, every module we've discussed, taxes and fees. One number, in writing.
- 2. What happens to the price when we grow? Adding 15 members to the roster or a second station shouldn't be a surprise line item.
- 3. What has your renewal price done for existing customers over the last three years? Intro pricing that doubles at renewal is a pattern, not an accident.
- 4. Which of the features we just saw cost extra? Demos routinely show the top-tier bundle. Get the tier you're actually quoted, then re-watch the demo in your head.
Fit & changes
- 5. Can this match how our agency already works — or will we adapt to it? Ask them to configure your actual workflow live, not describe it.
- 6. If we need a feature you don't have, what happens? A real answer includes who decides, how long it takes, and what it costs. "Submit it to our ideas portal" means no.
- 7. Who else our size uses this? A product built for 400-member metro departments will feel like it — ask for references from agencies your size, and call them.
- 8. What does the product look like on the device our people actually carry? Insist on seeing the phone/tablet experience, not just the desktop admin view.
Data & risk
- 9. Do we own our data? The contract should say yes, unambiguously.
- 10. Can we export everything, ourselves, at any time? "Contact support for an export" is a leash. Look for self-service export in usable formats.
- 11. What's the contract term, and what does leaving early cost? Month-to-month means the vendor has to keep earning you. Multi-year with penalties means they don't.
- 12. Where is our data hosted, and how is it secured and backed up? You want specifics: encryption, backup frequency, and who can access it.
Support
- 13. When something breaks at 0200 on a Saturday, what actually happens? Walk through the real path: who answers, how fast, and what counts as an emergency.
- 14. Is training included — initially and for every new hire after? Software your probies can't learn is software your department will abandon.
- 15. Who, by name or role, is responsible for our account? "The support team" is nobody. You want a person whose job includes you.
How we answer these
Fair's fair — here's our own scorecard. Build cost: $0. Pricing: one flat monthly rate, not per seat, includes every feature we build you. New features: included — custom is the product. Contract: month to month. Data: yours, exportable, always. Support: the people who built your software. Details on the pricing section of our homepage, and the reasoning behind the model in our custom vs. off-the-shelf comparison.
Put us through the 15 questions
Seriously — bring this list to a call. If our answers don't beat the vendor you're evaluating, you'll have lost 20 minutes and gained a negotiating position.
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