The desire to appear intelligent causes founders to avoid simple questions and instead anticipate needs. This leads to incorrect assumptions. Asking basic, even "stupid," questions like "Why did you take this call?" is the key to understanding the customer's real needs and ultimately closing the deal.

Investors should view a founder's desire to learn skills like etiquette not as a weakness, but as a strong positive signal. It demonstrates humility, introspection, and a drive for self-improvement—key traits for a coachable and successful leader. The capacity for growth can be more valuable than pre-existing polish, identifying them as better long-term partners.

Move beyond surface-level discovery questions. Asking 'What do you value most in a partner?' forces prospects to articulate their core needs for a relationship (e.g., responsiveness, consultation). Their answer quickly reveals if there is a fundamental values alignment, a better predictor of success than technical fit.

Transactional questions get transactional answers. A "story-worthy" question, like "Tell me about the moment you first sensed trouble with your supplier?", prompts a narrative. This approach extracts the emotion, context, and deeper story behind an issue, leading to more authentic connection and insight.

Asking questions that probe values, beliefs, or experiences—"deep questions"—can create surprisingly intimate connections in seconds, even with strangers like a barista. These questions invite authenticity and move beyond superficial small talk, making the other person feel seen and valued.

A founder asking an investor about their biggest blind spot during evaluation is a disarming and intelligent question. As shared by Maytha Agarwal of Defy, it forces the VC to self-audit their decision-making process in real-time, revealing their introspection and leading to a more honest, transparent conversation.

Building deep connections isn't just about asking probing questions; it's about reciprocal vulnerability. Super-communicators often volunteer personal information about themselves first. This signals safety and gives the other person implicit permission to share something equally intimate, creating a powerful bond.

To elicit candid answers from fund managers, the most effective technique is not the question itself but the silence that follows. Resisting the psychological urge to fill the space forces the manager to sit with the question, often leading to less rehearsed and more truthful responses.

The most driven entrepreneurs are often fueled by foundational traumas. Understanding a founder's past struggles—losing family wealth or social slights—provides deep insight into their intensity, work ethic, and resilience. It's a powerful, empathetic tool for diligence beyond the balance sheet.