What should you ask in a sales software demo?

Which sales software demo questions cover data and compliance

Start with where the data comes from, because every other feature depends on it. A good vendor answers these plainly; a vague answer is itself an answer.

• Where do contacts come from, and which privacy rules does that source follow?
• How are emails checked, and how is confidence shown to the user?
• Does the tool provide phone numbers, or email only?
• Is anything we upload or write used to train a model?
• Which security certifications are held today, and which are still in progress?

What should you ask about approval controls

Ask exactly which actions can happen without a person approving them. Sending email, writing to the CRM and starting a lead search all reach outside the tool, and you should know the default for each.

Then ask what a new user's default setting is, whether approvals can be required by team, and where you can see what ran. A demo account set to its most careful mode can hide what the product does by default.

Which questions for a sales tool vendor cover connections

Ask how each connection works, not only whether a logo appears on the page. A native connection, a connector built by a third party and a connection through MCP behave differently.

Ask whether data moves one way or both, whether it moves automatically or only when someone asks, who approves writes, and what happens when a connection expires.

How do you find out what is still in beta

Ask the vendor to label every feature in the demo as live, in beta or planned. Roadmap features look the same as live ones on a demo screen.

Ask for release notes and buy on what is live today. A planned feature can be a reason to check back later, not a reason to sign now.

What should you ask about pricing

Ask how the bill changes when you add a person, run more searches or use more AI, before you talk about discounts. Many tools combine seats with a usage allowance, and the allowance shapes the real cost.

Ask what happens when the allowance runs out, whether people who only view work need a paid seat, how annual and monthly terms differ, and what the trial includes.

How do you evaluate sales automation software with a real use case

Bring one real use case and ask the vendor to run it live in the demo. For illustration: five accounts from your target list, the leads the tool finds there, the research it produces and a first draft for one person.

Judge the output as you would a new hire's work. Would you send the draft? Do the facts hold up? Would your team use this every day?