A silent dissenter won't respond to "What are your concerns?". Instead, "soft-float" several potential objections, like giving them a multiple-choice question (e.g., "Is it our integrations, our pricing, or something else?"). This lowers the barrier for them to engage and allows them to latch onto a specific point, revealing their true apprehension.

Startup founders often sell visionary upside, but the majority of customers—especially in enterprise—purchase products to avoid pain or reduce risk (e.g., missing revenue targets). GTM messaging should pivot from the "art of the possible" to risk mitigation to resonate more effectively with buyers.

To avoid sounding pushy when asking critical questions about a deal's viability, frame them as necessary steps to ensure the customer's success post-implementation. This shifts the intent from closing a deal to building a successful partnership, encouraging open answers.