The Art of Booking A-List Podcast Guests
"Now What?" host Carole Zimmer shares her playbook for landing stars like Jane Fonda, Gloria Steinem, Joe Biden & Ethan Hawke
Hey Besties!
Who’s your dream podcast guest? What if it turns out they might be more attainable than you think?
When you see a show with a parade of high-profile guests, it seems like those producers and hosts have some kind of secret cheat code to the podcast booking video game. But maybe they’re just more comfortable with rejection.
For the season two premiere of Podcast Bestie, I had the pleasure of interviewing veteran journalist and Now What? host Carole Zimmer, whose guest list includes Gloria Steinem, Jane Fonda, Ethan Hawke, Joe Biden, Larry Charles, Gabriel Byrne, and countless other fascinating (and famous) people.
The advice I gleaned from Carole is advice so practical and encouraging for anyone trying to level up their own interview show.
Here are my biggest takeaways:
1. Booking great guests isn’t magic; it’s a numbers game
Even with decades of journalism experience at major publications, Carole still hears “pass” (or crickets) far more often than “yes.”
“I think I probably get—out of ten I think I get six nos. I’ll say maybe four people will say yes,” she estimated. And yet, she keeps asking because she only gets those four amazing yeses alongside the six rejections.
It’s consistent outreach that has built her enviable guest roster—and as it grew, each recognizable name made the next pitch a little easier. That’s the compounding power of social proof. And the inspiration I needed to go after my favorite big-name guests.
2. Your pitch email should prove you’re worth someone’s time
Carole doesn’t send generic requests. Instead, she personalizes every email by referencing the guest’s work, highlighting why she’s genuinely interested in talking with them in specific, showcasing recent notable guests, and linking to one of her newsletters so publicists can immediately see the quality of the show.
She also makes saying yes as easy as possible in terms of logistics. “I’m very flexible in terms of time, day, making it convenient for the guests to do it.”
3. Research is a huge competitive advantage
Nailing the research portion of a great interview isn’t rocket science. If your guest wrote a book, read the book. If your guest made a documentary, watch the documentary. Carole doesn’t believe in winging interviews. “I do A LOT of research,” she explained.
The goal isn’t to impress your guest with how much trivia you know about them. It’s to ask them questions nobody else is asking—questions that get at what really motivates them. Instead of rehashing their résumé, Carole is interested in uncovering “what makes these people tick.” That’s how conversations become memorable instead of just another stop on the press tour.
4. Let your guest tell their own story
One of Carole’s biggest lessons after nearly 200 episodes was to stop showing her homework. “When I started, I would tell people a story,” she recalled. “Now instead of telling a person’s story, I’ll just ask them to tell me and that I think is way better.” It’s a subtle but important shift.
Your job as an interviewer is to set up the guest to shine, not demonstrate everything you learned about them. It’s better to use those tidbits as openings for them to surprise both you and your audience.
5. Your interview notes should provide structure, not handcuffs
Preparation matters, but so does spontaneity. Carole writes a list of detailed questions before every interview, but she’s careful not to force the conversation back to her outline if something more interesting emerges.
“I will kind of go with it and then come back,” she said. That’s the sweet spot: enough preparation to stay organized and on track, yet enough flexibility to follow unexpected moments. Some of the best podcast moments happen when you’re willing to ditch the script for a worthy tangent.
And more…
This episode is packed with fascinating stories and nuggets of wisdom, including how Carole landed Joe Biden, why she still prefers in-person interviews whenever possible, and the surprisingly simple newsletter strategy she uses to promote every episode (kinda like I’m doing here).
If booking bigger guests and becoming a stronger interviewer is on your bucket list, my conversation with Carole is full of excellent advice you can put to use immediately.
Listen here:
And if you want Carole’s juiciest podcasting tips, become a paid subscriber for our bonus segment:
I’m teaching some upcoming classes you might be interested in:
The Multi-Passionate Writer’s Life (THIS IS SUNDAY!)
12 Months to a Full Memoir in Essays Incubator: Write Your Memoir in a Year (apply now)
How to Build a “Platform” for Writers Who Shudder at the Thought
Start a Newsletter to Supercharge Your Platform, Network & Business
How to Make 2027 Your Best Writing Year Yet: Manifest Your Writing Goals Seminar
So… ROLL CALL! 🗣
Who’s the dream guest you’ve been too intimidated to pitch? Drop their name in the comments below. Maybe this is your sign to finally send that email.