Professional allocators rarely receive feedback on their ability to question managers. Ted Seides found that hosting a podcast, which requires listening to and editing his own interviews, created an invaluable feedback loop that dramatically improved his information-gathering and due diligence skills.

For 20 years, Ted Seides never debriefed his own performance as an interviewer. Only when forced to listen to his podcast recordings did he create a feedback loop and improve his craft, highlighting a common blind spot for professionals who conduct interviews.

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.

To prevent guests from adopting a rehearsed, "idealized" persona, the podcast host starts recording as soon as they sit down. By eliminating formal cues like "Are you ready?", the conversation feels natural and unplanned, leading to more honest and unguarded responses that reflect the guest's true personality.

It is far easier to extract deep knowledge from experts, like a CEO, through a conversational podcast than by asking them to produce a polished written essay. Podcasting lowers the activation energy for sharing complex ideas.

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.

While AI can automate interview prep, it actually increases the value of being a great interviewer. Eliciting unique qualitative data through skilled questioning provides a proprietary information advantage that AI can then analyze, amplifying potential alpha.

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.

Andy Richter's technique for better interviews is to start recording the moment a guest arrives. This captures unguarded conversation before the formal "commercial vessel" of the show begins. Avoiding a stilted intro maintains a framework of real human interaction, leading to more authentic content.