I was chatting with a business owner about sales and this came up. They’re selling an AI workflow tool to businesses, and one potential customer has asked for three demos and loads of extra information but still won’t make a decision.

At what point do you stop chasing them?

Three demos would be my limit too, unless they’re giving you a very clear reason for the delay.

I’d rather ask what’s actually stopping them than keep sending more information.

I’d stop chasing.

Had this happen with hardware buyers. Loads of questions can feel like buying intent, but sometimes they’re just interested in the product.

I’d ask them what needs to happen internally before they can make a decision. If they can’t answer that, I’d move on.

One thing that might help here is figuring out whether you’re actually talking to a qualified prospect in the first place. We had a discussion on B2B market research and identifying buying intent that might be useful: B2B Companies - Market Research: We Need Your Help?

“Any update?” gets old very quickly 😂

I’d give them a reason to reply instead. Ask a proper question, give them a deadline, or just be upfront that you’re closing the conversation for now.

I like the “closing the conversation” approach. Sometimes taking the pressure off is what gets someone to finally give you a straight answer.

After the second or third nudge I'd stop changing the amount of chasing and change what the message asks. "Any update?" is easy to ignore. A single question is easier to answer, for example: is this still a priority this quarter, or should I close it off for now? If they have asked for three demos, it is also worth asking who else needs to sign off, because the person asking the questions is often not the one deciding. Once you have sent a polite "closing this for now, shout if it comes back up", leave it there. People tend to reply to that, or come back on their own later.