What do you want Process Street for the most?
Change isn't easy, and businesses don't undertake system overhauls and new implementations just for the fun of it. If there's no real problem the prospect is trying to solve, there's no real reason for them to buy. Establish pain (either from a known issue, or from a problem the prospect wasn't even aware of) before diving into other questions.
How have you tried to solve the problem so far?
This is an awesome sales question because their answer will virtually always offer insight into where in the buying cycle they are, as well as how their organization is structured. For instance, are they investigating other solutions? Are they trying to cobble together budget? Are they trying to get buy-in from key decision makers?
What led you to start looking for a change now?
If a prospect is looking to make a change, it’s important to understand why they are looking to make that change. Identifying catalysts that are driving a desire to implement change is incredibly important to your strategy. For example, did they just get budget for a solution? Is your prospect a new hire with a mandate for change? Do they have a lease or policy set to expire? Their answer can help you to identify how big of a priority buying your solution is.