To move beyond superficial questions, ask a candidate for their real-time assessment of their own performance. Their answer to what you like and what might be causing you pause reveals their ability to read a room, their self-awareness, and how they react under pressure.

Open-ended questions can be hard to answer, while leading questions feel trapping. Instead, ask an open question and immediately provide 2-3 potential answers as "leads." This makes it easier for the prospect to respond and makes the conversation feel collaborative, not interrogative.

Before giving feedback or answering a complex question, ask a clarifying question. This isn't just for the other person's benefit; it's a strategic tool to help you target your own response, ensuring it's relevant and concise.

Instead of asking leading questions that corner an interviewee, use open-ended prompts starting with 'how,' 'what,' or 'why.' This encourages expansive answers and genuine information gathering, whereas closed questions allow for simple, uninformative deflections, achieving no learning.

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.

Reading from a list of questions makes an interview feel robotic and signals a lack of active listening. The more effective method is to internalize the core points from a prep sheet and then put it away. This frees you to be fully present, listen actively, and let the conversation flow naturally.

An interviewer's goal is to learn, not to talk. By dominating the conversation, as when the interviewer's question was twice as long as the answer, nothing is learned. A good rule of thumb is to limit your own speaking time to 10-15% to maximize information gathering.

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.