“What keeps you up at night?”

In enterprise sales, effective discovery is not about fishing for generic pains but about delivering insightful, thought-provoking questions that differentiate you from competitors and win the prospect's trust. Questions such as "What keeps you up at night?" have become clichéd and often signal lack of preparation or laziness, especially when repeated across vendors and webinars. To elevate your strategic selling, you need a deep understanding of the customer's industry, business goals, and pain points before engaging in conversations. Researching their business context, recent challenges, and market trends enables you to tailor questions that reveal underlying tensions and unspoken problems. Insightful discovery questions should make prospects stop and reflect, encouraging a reframe of their situation rather than merely confirming surface-level issues. Building tension during discovery creates urgency and highlights the risks of inaction, which is essential in enterprise sales cycles. This tension drives motivation to explore solutions more seriously. Moreover, discovery is also an opportunity to demonstrate empathy and business acumen, proving that you genuinely care about solving their core problems rather than selling a product. Incorporating this mindset in your sales discovery process means: - Avoiding lazy or overused questions that do not add value. - Showing you understand specific challenges faced by enterprises at a strategic level. - Using questions that challenge assumptions and open pathways to new insights. - Guiding prospects to rethink their issues by focusing on impact and strategic priorities. Ultimately, earning trust in B2B and enterprise sales requires demonstrating professionalism, preparation, and genuine insight. By asking better questions and building meaningful tension, sales professionals can transform discovery from a routine Q&A to a powerful, relationship-building conversation.