To truly understand a prospect's decision-making process, ask for more than you expect to get, such as requesting to be part of their internal evaluation meeting. Even a "no" often prompts them to reveal more about their process, criteria, and stakeholders than a standard discovery question would.

CEOs provide a curated view of their company's culture. To get an accurate picture, talk to people who have left the organization on good terms for an unfiltered perspective. Also, ask behavioral questions like 'What would you tell a friend to do to be successful here?' to uncover the real cultural DNA.

Tasked with gathering user feedback in a mall for a job interview, the speaker failed with a product-centric pitch. He succeeded by reframing the request as a personal, empathetic plea: "I'm on a job interview... Would you do that just so I can get this job?" This leveraged social goodwill over transactional value.

To clarify difficult talent decisions, ask yourself: "Would I enthusiastically rehire this person for this same role today?" This binary question, used at Stripe, bypasses emotional ambiguity and provides a clear signal. A "no" doesn't mean immediate termination, but it mandates that some corrective action must be taken.

Instead of trying to find the perfect words, preface difficult feedback by stating your own nervousness. Saying, "I'm nervous to share this because I value our relationship," humanizes the interaction, disarms defensiveness, and makes the other person more receptive to the message.

A candidate can claim they want growth, but their resume tells the real story. Scrutinize *why* they moved between specific companies. A move for a bigger salary versus a move to work under a renowned leader reveals their actual priorities far more accurately than their interview answers.

Ineffective interviews try to catch candidates failing. A better approach models a collaborative rally: see how they handle challenging questions and if they can return the ball effectively. The goal is to simulate real-world problem-solving, not just grill them under pressure.

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.

Don't be paralyzed by the fear of making a bad hire. View hiring as an educated guess. The real knowledge comes after they've started working. Firing isn't a failure, but the confirmation of a mismatched hypothesis. This reframes hiring from a high-stakes decision to an iterative process of finding the right fit.