You asked AI to make an email sound more professional. Forty minutes later, Claude knows your entire reporting structure, your issues with authority, and why “quick sync” feels like a threat. Aaron Berger and Heather Vontava talk about what happens when your AI assistant becomes the coworker you vent to, the therapist you never booked, and the suspiciously enthusiastic supporter of your side of every argument. They get into overly agreeable bots, office politics, privacy, and the difference between getting perspective and repeatedly asking until the computer admits you were right. Plus, “work Claude” versus “street Claude,” rehearsing difficult conversations, and why changing Kevin’s name to “K” isn’t witness protection. If you’ve ever asked a chatbot, “Am I being unreasonable?” while carefully leaving out the part where you were, this episode is for you.
