ask them to show you how they currently do it. Talk about which parts they love and hate. Ask which other tools and processes they tried before settling on this one. Are they actively searching for a replacement? If so, what’s the sticking point? If not, why not? Where are they losing money with their current tools? Is there a budget for better

” Get specific about examples in the past to get real, concrete data.

ask them to show you how they currently do it. Talk about which parts they love and hate. Ask which other tools and processes they tried before settling on this one. Are they actively searching for a replacement? If so, what’s the sticking point? If not, why not? Where are they losing money with their current tools? Is there a budget for better

A question like “why do you bother” points toward their motivations. It gives you the why. Rule of thumb: You're shooting blind until you understand their goals.

People stop lying when you ask them for money.

How much does the problem cost them? How much do they currently pay to solve it? How big is the budget they’ve allocated? I hope you’re noticing a trend here.

It’s not about “how many” meetings. It’s about having enough for you to really understand your customers. You want to talk to them enough that know them in the same way you know your close friends, with a firm grip on their goals, their frustrations, what else they’ve tried, and how they currently deal with it.

They’re the company who will commit way before it makes rational sense to do so.

“What are your big goals and focuses right now?”