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In this episode of convos.dev, Jess and Chris dive into the world of hiring and interviewing for tech roles. Chris shares what he's learning from screening 300+ applicants for a technical writer role at Resend — from red flags in applications to the culture-fit questions he's found most revealing. Jess brings the skeptic's take, drawing on her experience with mock interviews and candidates who game the system. They also discuss AI in interviews, the difficulty of predicting long-term fit, and why hiring is one of the most expensive decisions a startup makes. Plus: a rant about the lack of good AI slide tools, Claude Island, and some fun show & tell. 0:00 Intro 2:59 Screening 300+ applicants — what stands out 5:21 Should you use AI to screen candidates? 7:04 Culture fit: why it matters so much at startups 10:51 What makes a candidate stand out in interviews? 12:07 Why it's so hard to vet for long-term fit 14:05 The most revealing interview questions 22:24 Catching a candidate using AI during an interview 25:01 Hiring is expensive — reflections on the process 25:37 Tool Review 30:05 Show & Tell Links https://convos.dev : Submit questions and feedback