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.

To get past a curated interview persona, ask a candidate to describe a time they had to work with someone they viscerally disliked. Their answer reveals their true approach to conflict, blame, and collaboration under pressure.

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.

Don't start an interview on the back foot by reciting your resume. Immediately reframe the conversation by asking what about your background excited them. This forces them to reveal their needs and shifts the dynamic to a consultation, not an interrogation.

Engaging an executive late in a deal requires a different approach than initial discovery. Bring them up to speed on the project, frame the conversation around what you hope to achieve, and then ask high-level questions that connect to their strategic priorities to respect their time and position.

Instead of only asking questions, leaders should begin interviews by explaining their personal values. This gives candidates a clear picture of what it's like to work with you on good and bad days, fostering a deeper connection and allowing both parties to assess the fit more honestly.

When asking direct, potentially uncomfortable questions about performance or risk, start with a softening phrase. Saying "This might feel out of bounds..." or "I'm not sure how to ask this..." makes the prospect more comfortable opening up about sensitive executive-level problems.

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.