Citing Oprah Winfrey, Rubenstein argues the key to great interviewing is not having the best questions but being a great listener. True listening allows the interviewer to pivot and follow up on unexpected answers, turning a rigid Q&A into a genuine conversation that uncovers far deeper insights than a prepared script ever could.

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The foundation of clear communication isn't eloquence but active listening. The goal is to understand the other person's perspective before formulating a response, which also helps prevent reactive, stress-induced replies and makes others feel heard.

The best interviews aren't about one person dominating. They're like a long tennis rally where both participants hit the ball hard but aim to keep the conversation going, creating a more engaging and insightful exchange for the audience.

The goal of asking questions isn't just for you to gather information. It's a Socratic dialogue designed to help stakeholders think differently and arrive at the real need themselves. By guiding their thought process, you build deeper alignment and co-create a better solution, rather than just extracting requirements for yourself to fulfill.

Instead of asking standard discovery questions, top performers pose strategic questions that require joint exploration. This shifts the dynamic from a sales pitch to a collaborative problem-solving session, creating a deeper partnership and revealing unforeseen opportunities that standard questions would miss.

Paraphrasing is more than just a tool for checking comprehension. Citing research from Harvard's Alison Wood Brooks, the speaker notes it also deepens your connection with the other person. The act of listening in order to paraphrase also forces you to focus more intently on the core message.

'Radical listening' expands on active listening by incorporating internal data. This means paying attention to your own emotional reactions and intuition during a conversation, as these signals can reveal unspoken truths and lead to more profound questions and insights.

True connection requires humility. Instead of trying to imagine another's viewpoint ("perspective taking"), a more effective approach is to actively seek it out through questions and tentative statements ("perspective getting"). This avoids misreads and shows genuine interest.

The most effective salespeople are not those with the 'gift of gab,' but those who master listening. Influence is created by asking questions that get prospects to reveal their problems, then using that information to create a value bridge to your solution.

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.