Ask Three Questions Before You Demo
Nobody wants to join a call with a sales rep and get talked at for 40 minutes. Think about how many bad demos you've sat through yourself, a generic walkthrough of something that had nothing to do with what you needed.
So I open every demo the same way: "Look, I've got three questions up front so I can make sure I show you something that actually answers the problem you have. I don't want to spray and pray, because that's a waste of your time and mine. Are you OK if I ask you three questions first?"
Almost nobody says no. And now you're running the call.
When they ask why they're on the call
Every so often a prospect shows up and says something like "so what am I doing here?" I turn it back on them. "I wish I could answer that for you. You accepted the meeting and you're here, so thank you. What's your goal for today?"
Then ask an open question about a problem you solve. If they tell you they don't have that problem, believe them. "OK, thanks. I work with people for whom this is a real point of friction. I'm happy to show you a demo, but it doesn't sound like you've got the friction we solve for." Some of them will tell you about a problem right then. Some won't, and you just saved yourself a follow-up sequence.
Demo their world
As a buyer, I'd way rather see my own stuff in a demo than a general tour. If you can use their data, their workflow, or their use case, do it. A custom demo tells them you listened, and it lets them picture the product working for them.
"I just want to click around"
When someone says "we just want to try it out," my cynical brain hears somebody who doesn't want to buy. Sometimes that's wrong. Find out by asking what specifically they're looking for. What's your go or no-go? What does success look like?
If they want a trial, treat it as a mutual evaluation. Before you hand it over, write down the decision criteria they gave you, the show-stoppers, and what success looks like, and send it to them. They don't need to sign it. Book a 15-minute check-in every week or so while the trial runs. You're the CEO of your deal, and part of that job is teaching people how to buy from you.
Late in the cycle, ask for the deal-breakers
Near the end of a demo cycle, ask straight out: "What are the deal-breakers? What are the non-negotiables? What has to be true for you to go ahead?" You'd much rather hear it now than in procurement.
Happy selling!