Open-ended questions can be hard to answer, while leading questions feel trapping. Instead, ask an open question and immediately provide 2-3 potential answers as "leads." This makes it easier for the prospect to respond and makes the conversation feel collaborative, not interrogative.
Begin discovery by stating, "I talk to [Persona] all day, and they struggle with X, Y, or Z. Does that sound like your world?" This establishes credibility, provides social proof, and makes it easier and safer for prospects to admit they have a problem.
Simply focusing on a prospect's pain is insufficient. You must also uncover their desired future state. The most effective sales approach connects the "pain of the now" with the "gain of the future," creating a complete picture of why they need to change.
A key goal in any sales call is to sell the next action, whether it’s a demo or a meeting with leadership. Reps must clearly articulate *why* the prospect should take that next step, treating it with the same importance as selling the overall product.
If you're unsure what problems to ask about in discovery, start with your product's key benefits. The inverse of a benefit is a problem. If you "save time," the problem is "wasting time." Then, dig into the specific activities causing that waste.
Avoid pushing to quantify business impact with operational contacts who don't focus on it. A controller cares about chasing receipts, not overall revenue loss. Tailor discovery to the persona's actual sphere of influence and save the big business case for the economic buyer.
If a prospect demands to see the product early, don't resist. Instead of front-loading all discovery, weave your questions into the demo itself. Ask situational questions when you show a relevant feature, allowing you to discover information while satisfying the prospect's request.