To quantify a problem without being confrontational, use a "push-pull" approach. First, "push" by suggesting a number ("This probably costs you $45k..."). Then, "pull" back by offering an out ("...or is this pennies in the barrel?"). This relieves pressure and encourages an honest, quantitative response.
Instead of asking broad questions like "What are your challenges?", present a menu of common problems: "Typically, frustrations are A, B, or C. Which is it for you?" This makes it easier for prospects to articulate their pain and guides them toward the specific problems your solution excels at solving.
The bridge between a five-figure operational problem and a six-figure executive problem is often an emotional, painful story. Ask a "magic moment" question like, "When did you actually realize this was a problem?" to elicit the specific event or narrative that created the business impact and urgency.
Discovery has three levels: Situation (what they do), Operational Problem (a day-to-day annoyance for a champion), and Executive Problem (the business impact). Sales reps fail when they solve operational issues without connecting them to the executive-level "so what" that justifies a purchase.
To understand the problems your product solves, find the feature-benefit statements on your company's website and invert them. "Get results in minutes, not days" becomes the problem "Our background checks take days, not minutes." This creates the foundation for your discovery questions.
Not all business problems are created equal. Time savings often translate to five-figure cost savings, which may not be compelling. The most powerful executive problems are "six-figure problems"—major risk mitigation (avoiding lawsuits), significant revenue generation, or replacing other large costs.