How One PE Operator Aced a Termination Talk in 30 Min
A new portco CEO cloned the person across three ChatGPT windows — profile, role-play, and a Kim Scott critic — and HR called the result the most effective talk they had witnessed.
Best Ever
Conversation HR had ever witnessed
Jeremy Utley
Adjunct Professor, Author, Podcaster
Stanford University, Ideaflow, Beyond the Prompt: How to Use AI in Your Company
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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 demonstrated a three-window ChatGPT workflow: first, prompting the AI to interview him and build a psychological profile of the person being terminated; second, feeding that profile into a new window and role-playing the conversation via voice mode; third, having a third ChatGPT window act as Kim Scott (author of Radical Candor) to deliver brutally honest feedback on his approach. The operator practiced progressively harder scenarios — including a 'bad day' version — within 30 minutes. He then continued refining the approach independently before the actual conversation.
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.
AI Role
The AI performs three sequential roles across a three-window ChatGPT workflow: first, it interviews the user to build a psychological profile of the person being terminated; second, it role-plays the termination conversation in voice mode using that profile; and third, it simulates the perspective of Kim Scott (author of Radical Candor) to deliver critical feedback on the user's conversational approach — escalating scenario difficulty on request.
Impact
"Most Effective Conversation" Recognition
The PE operator conducted his termination conversation and received unsolicited praise from the head of HR, who called it 'the most effective conversation I've ever witnessed in the company' — without knowing AI had assisted in the preparation.
Rapid, Low-Cost Preparation
The entire preparation cycle — profiling, role-play practice, and expert feedback — was completed in approximately 10–15 minutes using off-the-shelf ChatGPT, requiring no proprietary tools or significant investment.
National Park Service: 40 Days Saved Per Employee
A non-technical NPS facilities manager built a custom GPT in 45 minutes that compressed federal statement-of-work paperwork from 3 days to under 1 hour per project. One colleague alone saved an estimated 40 days of labor per year (20 SOWs/year × 2-day reduction). Scaled across the park service, Jeremy estimated 10,000+ days of labor could be saved annually.
Implementation Complexity
The implementation uses only off-the-shelf ChatGPT with no custom development, integrations, or proprietary tooling — the entire workflow is constructed through prompt design across three standard browser windows. Complexity is negligible from a technical standpoint; the value lies entirely in the prompt engineering methodology.
Best Fit For
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.
