🎙️ Executive Series — Episode 10: Objection Anticipated — Turning AI Into Your Toughest Opponent

In this Executive Edition of Practical Prompting, Alex and his AI co-host, Practically Speaking, turn a tactic into a habit: use AI to surface objections before your stakeholders do—so decisions get faster, safer, and sharper.

Act I: The Couch Dilemma → The Hidden Criteria Play Alex walks through replacing a couch in hours, not months, by converting “vibes” into ranked constraints (back height, seat depth, dog-proof leather) and reframing the use case (reading + tea, not home theater). The result: fewer, better options and a cleaner ask. Lesson: many “objections” are your own unspoken criteria. Name them, and the noise falls away.

Act II: AI as Your Objection Simulator We zoom out to leadership. Before your deck leaves your desk, run an AI premortem: simulate CFO/COO/Legal—or whichever roles are actually in the room—merge duplicates, and return only the top three objections with evidence and a two-sentence counter. Package it in a one-slide “Likely Objections” box and a Decision Card (Goal, 90% plan, Top-3 risks + counters, Clear Ask). This reframes prep from defensive to proactive and trims approval latency.

🎯 Your Challenge: Run the meta-prompt on one live proposal today. Email alex@lololai.com with your Top-3 objections and the single riskiest assumption you’ll test this week.

Disclaimer: Views expressed are Alex’s own and do not represent any employer; no confidential information is shared.

Connect: alex@lololai.com