The Challenge
A private equity operator, newly installed as CEO of a portfolio company, needed to have termination conversations with senior leaders who had lost their drive post-liquidity event. HR provided standard training materials, but the conversations required psychological nuance the operator didn't feel equipped to deliver. With significant organizational stakes and no safe space to practice, he turned to Jeremy Utley for guidance on whether AI could meaningfully help him prepare.
What They Built
Utley built a three-window ChatGPT workflow using ChatGPT Voice and O1: one window to profile the person being terminated, one to role-play the conversation via voice mode, and a third to deliver Kim Scott-style feedback on the executive's approach.
Utley's approach centered on a structured multi-window prompt architecture rather than any custom technology. The first ChatGPT window was prompted to conduct an interview with the operator, gathering everything known about the person being terminated — their personality, history, emotional state post-liquidity, and likely resistance patterns. The AI used this information to build a detailed psychological profile of the counterpart.
That profile was fed into a second ChatGPT window operating in voice mode, which role-played the conversation as the person being terminated. The operator could run the conversation, pause, restart, and replay progressively harder versions — including a "bad day" variant — building fluency and composure in low-stakes repetition. A third window was then prompted to respond as Kim Scott, author of Radical Candor, delivering direct feedback on what the operator said, how he said it, and where his approach fell short. The operator practiced independently after the session. The entire preparation loop ran in under 30 minutes using only off-the-shelf ChatGPT with no custom development, integrations, or proprietary tooling. Infrastructure and Integration Points are not applicable; this is a prompt-engineering-only workflow.
Senior executives and operators at PE-backed companies, public company CEOs, and C-suite leaders who regularly face high-stakes interpersonal conversations (terminations, negotiations, board presentations) and want a private, low-cost environment to prepare. Also organizations wanting to drive AI-first culture from leadership down.
