An important question I like to get answered on the initial product demo: If you don’t solve the challenges you are having today with my product or a product like mine, what will be the cost/impact to your business?  

Occasionally I get a really great answer from a prospect when I ask this after a bit of discovery. But at least 9 times out of 10 I get an answer that is telling.  

Why do I ask this question: because if my prospect ever plans to purchase what I am pushing, they will have to change what they are doing currently, and adopt a new platform and process. And I need to confirm that there exists a good enough reason to do this. Afterall, for them to part with budget, they usually need a pretty good reason. 

So when do I ask this question: once the prospect shares with me what their current process is, and after I ask what sorts of shortcomings exist in that status quo. 

How this question helps my sales process: it helps me fight against the urge to broadly claim that I can help solve their challenges just because I THINK I know best. Example: after a prospect shares pains that you know you solve for, it is tempting to claim (broadly) that “I [you] can help them [prospect] with that [business challenges]”. The prospect shares something helpful to you about their daily work, and you bridge the conversation with something that is hard to believe at best, and condescending at worst. Instead, take the opportunity to dive even deeper and understand why it comes at such a cost to their business.

If nothing else, you will establish a bit more clarity.