There are interviews, and then there are conversations. The best podcast hosts know the difference, and the gap between the two is harder to close than it looks. 

In this bonus episode, I get to turn the tables. Jessi Hempel (host of the podcast Hello Monday and senior editor-at-large at LinkedIn) and I nerded out on the craft we both love: what it actually takes to walk into an interview prepared, how to stay present when a guest goes flat, and the moment a scripted exchange becomes something neither person planned for. 

If you've ever wondered what goes on in a host's head before and during a recording, this one pulls back the curtain. 

Jessi and I discuss: 

• Why Jessi walks into every interview with no notes, and the preparation habit that makes it possible 

• The AI experiment that went badly wrong, and what it taught Jessi about how not to prepare 

• How to tell whether a podcast host has actually read the book (there's a tell, and writers always spot it) 

• What to do when a guest is giving you nothing and the conversation is going nowhere 

• The hardest interview challenge to crack, especially with big-name guests on book tour 

• The moment an interview tips into a real conversation, and why you can't fake your way there 

Key quotes 

"The process of slowing down and sitting with material and stumbling over it and forgetting a lot of it, but just sort of tracing my own mind to figure out where I feel curious about it, is the process of preparation." 

"The best interviews tip into conversations." 

Connect with Jessi Hempel on Instagram. and LinkedIn. Check out her newsletter and listen to her podcast Hello Monday. 

If you haven't already, listen to the main episode with Jessi - where she gets into what actually works on LinkedIn in 2026. Check it out here.