Don't spend too much time around someone whose primary way of engaging with life is as a martyr. When suffering becomes your identity, you only see the hard parts of life.
James Clear
Last week, I interviewed one of my favorite writers. I first read his writing in Esquire when I was a teenager, and was swept away by how he told stories. I didn’t know it then, but his work would inspire me to pursue storytelling as a career.
Near the end of our interview, I asked what new projects he was excited about. His answer captured my attention—I wanted to be a part of it. But who was I to ask him, a hero in my life?
I did it anyway.
To my shock…he said yes.
When I listened back to the recording of our interview, I can hear myself saying, after we hung up, “If I hadn’t asked… If I hadn’t asked…”
If I hadn’t asked, I wouldn’t have booked my first interview that got me into podcasting.
If I hadn’t asked, this newsletter wouldn’t exist.
If I hadn’t asked, I wouldn’t have spent time with my childhood hero and had the chance to collaborate with him on a project.
On the other side of sweaty palms and doubt lies possibility. I’ve found time and time again getting there can be as simple as asking for what you want.
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Industry game changers and valiant minds from creative professions share their wisdom, adversities, and paths to innovation.
Elie Honig, former mafia prosecutor and host of Up Against the MobElie Honig is a CNN Senior Legal Analyst who worked for 14 years as a federal and state prosecutor. He is the national best-selling author of two books for HarperCollins, “Hatchet Man” (2021) and “Untouchable” (2023). In 2022, he was nominated for a national Emmy Award for “Outstanding News Analysis: Editorial and Opinion.” Honig writes a weekly column for New York Magazine and Cafe.com, and he hosts a true crime podcast about the mafia, Up Against the Mob. Honig graduated from Rutgers University (where he now teaches) in 1997 and Harvard Law School in 2000.
The pressure in the courtroom is way, way higher than in a podcast. Because the stakes are so real. And it's all live, it's all on the spot. In podcasts, we have the gift of editing. They're similar in the sense there’s the pressure to tell a compelling story in a compressed timeframe.
My work as a prosecutor helped me be a better interviewer for podcasts. You learn to ask the relevant questions, you learn to challenge people, you learn to phrase questions in a way that avoids boring or non-committal answers.
I definitely prefer podcast interviewing over courtroom interviewing. It’s liberating. The rules of evidence are designed to very carefully filter out information from a jury because we don't want jurors ruled by passion, prejudice, or emotion. But those same things are crucial to real-world storytelling.
But I still have that little voice in my head. In court, you can't really ask about emotions, unless maybe it’s a victim and fear is an element of the case. So you can't ask the mother of a murder victim, how did you feel when you found out your son was murdered? You would absolutely ask that on a podcast, but that would be wildly objectionable in court.
There's a fundamental skill that trial lawyers and prosecutors learn, which is taking a complex mass of information and presenting it in a way that's digestible and engaging. That's what you do when you stand up and address a jury. It’s very similar in podcasting.
The number one rule for interviews, in court or in podcasting, is preparation. You need to know everything about the person and their connection to the topic at hand.
We were trained as prosecutors to have one thought or idea per question. The technical term for it legally, if you do the opposite, is called a compound question. Let’s say you ask, “Were you in New York City on March 14th and did you witness a traffic accident?” That's actually two questions. A compound question is confusing for the interviewee and the audience. It also allows the interviewee to either dodge or collapse or answer only whichever part they want to answer. So one thought per question, and ask short, direct questions.
A nice little tactic is if you get a non-responsive answer or a sarcastic answer—just repeat the question.
It's pretty effective to just ask, “How did you feel when that happened?” “Did that surprise you?” is a good question. “What did you think when you saw that?” The kind of questions you would ask if it was your good friend and there was no microphone on.
In the second episode of season two of Up Against the Mob, our main star of the show is a cooperator named Anthony Arillotta. He talks about how he murdered people. And Anthony's got an extreme personality, but he and I have a good relationship. I know how to relate to him. I've known him for years, he was my witness. And Anthony, he's talking about how he was put on a hit and he shot this guy nine times. And I asked, do you have any regrets? And he goes, we shouldn't have driven down from Massachusetts to the Bronx, because we left too many evidentiary clues for you guys. And I'm like, no Anthony, I don't mean tactical regrets. I mean emotional regrets.
I have questions ready, but I’m not tied to a script. It's one of the biggest mistakes you can make because then you're not really listening. And you're not really following up.
When you get an unexpected answer in court, that's bad news. When you get an unexpected answer on a podcast, that's the best-case scenario.
People often ask me which is the most accurate of all the mob movies and shows. I've always said The Sopranos and I stand by that with one big exception. The Sopranos shows the grind of the mob. It shows the day-to-day stress and fear and tension and backstabbing that goes into it. The one thing I would say is way more people get killed in The Sopranos than in real life. Way more.
I always try to create a visual for real-life “characters” in the story. There's one guy, Big Al Bruno, who’s dead now but was a key figure in the story. And I asked everyone, okay, what did Al Bruno look like? And the descriptions are hilarious. Someone said this guy had a belly the size of a dumpster. One guy said he wore sunglasses everywhere he went, even indoors at the strip club. Those details can help paint a picture and tell you a lot about someone.
If you're telling a complicated story, you have to simplify it without dumbing it down.
Don't assume how much your audience knows. There are times when certain things require a bit of explanation without being condescending. If there was a term used by someone in an interview, either I would ask them, “What does that mean?” or I would make it clear with one or two sentences in narration.
It's one thing for you to tell a jury, “This was a horrible, devastating event.” It's another thing to go, “You remember the testimony of Frank, who got shot nine times? And he told you about how he dragged himself out of the car…” You're retelling the story, you're evoking the emotion through the facts of the story. You're not evoking the emotion by preaching. And I think it's much more effective to let the facts evoke the emotion than to bang on a pulpit and tell your audience they should be feeling a certain way.
A single memorable line from somebody who was at the event or somebody who experienced the event is going to be way more powerful than the narrator's retelling or characterization of it.
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