Sales reps often get stuck trying to ask smart-sounding questions they find online. The real breakthrough is focusing on understanding the prospect's current state and identifying what information is missing to build a business case, which will naturally lead to the right questions.
Buyers don't want to educate you; they want to feel understood. Begin calls by presenting a hypothesis based on your research. This signals expertise, builds trust, and fosters a more natural, collaborative conversation rather than an interrogation.
Prospects often state facts like "our sales process is complex." This is not a problem that gets budget. AEs must dig deeper for the root cause (e.g., single-threaded deals) and then the business problem (e.g., low win rate affecting fundraising) to build a compelling case for the CFO.
Most AEs get stuck at 'Level 2,' where discovery is a stage focused on understanding the problem. Elite 'Level 3' sellers see discovery as a continuous process used throughout the entire deal cycle to build the business case, drive consensus, and facilitate the buying journey.
Late in a deal, a team met a Global SVP who had different priorities than the champion. Instead of forcing it, the AE pivoted. They worked with the champion to find a new executive sponsor (a Mid-Market VP) whose business needs aligned, ultimately saving the deal.
Engaging an executive late in a deal requires a different approach than initial discovery. Bring them up to speed on the project, frame the conversation around what you hope to achieve, and then ask high-level questions that connect to their strategic priorities to respect their time and position.