Drawing an analogy to legendary music producer Rick Rubin, an investor's role is to help a founder find the most authentic and compelling version of their own story. The goal is not to invent a narrative, but to draw out the founder's core truth and channel it through their company.

To understand a candidate's true drivers, ask them to walk through every major career decision they've made, from college choice to job changes. This narrative reveals patterns and motivations—such as status-chasing, financial incentives, or problem-solving focus—far more effectively than direct questions.

To gauge a founder's drive and potential for greatness, ask if they have ever been in the top 1% of any field, even an esoteric one. This unconventional question serves as a powerful proxy for ambition and the willingness to push through challenges, regardless of their professional background.

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.

The simple question "What motivates you?" can be a powerful filter. A Forterra leader was once told by a banking vice chairman that being motivated by "team mission" over money would make for a difficult finance career. This advice proved correct and became his favorite question to uncover a candidate's core intrinsic drivers.

To win allocations, VCs should move beyond product and market discussions to a deeply personal conversation about what irrationally drives a founder. Most VCs don't ask about this, and exploring these core motivations builds a unique relationship that secures a spot in the round.

Instead of generic interview questions, ask what truly motivates a candidate and what they'd do for a hobby if money weren't an issue. The way they describe these passions reveals their energy, personality, and core drivers far more effectively than rehearsed answers about work experience.

A founder deep in the idea maze can articulate not just their current path, but also the alternatives they considered and why they were rejected. This demonstrates a profound understanding of their domain and problem space.

To truly understand a founder, Katelin Holloway bypasses typical pitch questions. She engaged one founder in a conversation about wormholes and the time-space continuum. This abstract dialogue revealed how his brain worked and his core values, giving her conviction in him as a person, not just his idea.