Standard discovery questions about 'pain points' are too broad. Instead, focus on concrete 'projects on their to-do list.' This reveals their immediate priorities, existing attempts, and the specific 'pull' that will drive a purchase, allowing you to align your solution perfectly.
Related Insights
The discovery phase of a sales call isn't a generic interrogation or a prelude to a demo. Its only goal is to understand the customer's PULL: their specific Project, its Urgency, the other Options they've considered, and the Limitations of those options. Only then can you effectively position your product.
True product demand lies in the gap between what customers are currently doing (observable on their calendar) and their ultimate goals (their mental to-do list). A successful product closes this gap, better aligning a customer's actions with their underlying objectives. This mismatch is where "pull" is found.
Most problems customers describe are "pain points" they won't act on. You can't distinguish these from real, actionable demand ("pull") through interviews alone. The only true test is presenting a viable solution and attempting to sell it. Their reaction—whether they try to pull it from you—is the only reliable signal.
Don't just solve the problem a customer tells you about. Research their public strategic objectives for the year and identify where they are failing. Frame your solution as the critical tool to close that specific, high-level performance gap, creating urgency and executive buy-in.
Don't pitch features. The salesperson's role is to use questions to widen the gap between a prospect's current painful reality and their aspirational future. The tension created in this 'buying zone' is what motivates a purchase, not a list of your product's capabilities.
When a prospect gives one-word answers, repeatedly and politely ask "Can you give me an example of that?" or "Can you be more specific?" This simple loop forces them to move from vague statements to the concrete details needed to build a case for your solution.
Standard questions like 'What's your biggest pain point?' often yield poor results. Reframing the question to what work a customer would offload to a new hire bypasses their pride or inability to articulate problems, revealing the tedious, high-value tasks ripe for automation.
To sell effectively, avoid leading with product features. Instead, ask diagnostic questions to uncover the buyer's specific problems and desired outcomes. Then, frame your solution using their own words, confirming that your product meets the exact needs they just articulated. This transforms a pitch into a collaborative solution.
Buyers often volunteer the exact details of their problem—their project, its urgency, and their frustration with current options. However, traditional sales training teaches founders to ignore these cues, interrupt the customer, and pivot to pitching their solution, thereby missing critical information.