On with Kara Swisher Isaac Chotiner on Confrontation, Curiosity, and Being the 'Interview Assassin'
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Jan 5, 2026 
Isaac Chotiner, a staff writer for The New Yorker, is known as the 'interview assassin' for his confrontational questioning style that unveils truths from prominent figures. He discusses his preparation for tough interviews and shares insights from his viral Q&As with Karine Jean-Pierre and Cass Sunstein. Chotiner also explores the fine line between opinion and neutral questioning, the dynamics of declining access to guests, and reflects on the important stories shaping the political landscape for 2026.
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Phone Interviews Enable Tougher Questions
- Isaac Chotiner prefers phone interviews because not seeing a guest makes confrontational questioning easier.
- He says phone interviews let him push harder in ways that feel harder face-to-face.
Tailor Prep To Topic Knowledge
- Prepare differently depending on whether you already know the topic or are coming in fresh.
- Read widely in your subject area and line up experts before the interview.
Write Only What You Need
- Use notes and selectively write exact questions when precision matters.
- Keep structure loose so you can follow interesting turns in conversation.