1. Never ask “does this make sense” - instead ask HOW and WHAT questions Ie "how does this compare to how you’re doing things today:" "What value do you see in doing it this way? This will get the customer thinking about the upside."
2. Relate every feature back to a problem - when you show a tool, you should be able to say “mr customer, you said X, and Y was the impact, this is how we will address that problem”
3. Start with reducing the cost of change - even before you demo your product start with how easy it is to move and what the steps look like (at a high level). Also prepare tabs so you're not jumping around in the demo making it confusing.
4. Bring up your own weaknesses - every tool has weaknesses, bring up yours, it’s going to come up anyway in one way or another and rather you bring it up to build a tonne of trust. “I want to call this out really early on, we don’t do inventory management, you’d need to use another system for that”.
5. Give the customer a way out - tell the customer at the start of the demo “ if at any point in time you feel its not a fit, that is 100% fine, please literally interrupt me". This will build trust and help you have a more meaningful conversation.
6. Summarise challenges - customers are juggling multiple priorities. Bring them back to why we are here before showing the product and do a summary first - the customer has a million things going on, your product isn’t their priority, so bring up the compelling reasons we’re here in the first place.
7. Set expectations for what will happen at the end of the call and even be be funny/extreme about it “usually what we do is leave 10 minutes at the end to decide what to next. On the one hand you might think we’re the worst thing you’ve ever seen & that would be sad but that’s totally fine-and then we’d just part ways as friends, OR on the other, if you think we’re a fit, then we’d discuss XYZ (next steps ie commercials and what implementation looks like).
8. Call out silence - If people are quiet try get engagement to draw out objections and ensure people feel bought in to making the change by feeling heard. “Judging by the silence, feels like this isn’t that impressive?” or “Dan, you’ve been quiet, would love to know what you think so far?”
9. Don’t try know everything - if you don’t know an answer to a question just say so and be direct about it, note it down and tell the customer you’ll followup via email.
10. Be self depreciating - don't try to be so smooth, be human. For example, if you have an implementation team, tell the prospect that luckily for them much smarter people would be in charge of actual onboarding and setup once they get started ;-)