40-60% of Executives Needed a Devil's Advocate
A prompt that interrogates the career decision you've already half made.
Inside this issue:
The 18-month number that turns a $400k career decision into a coin toss
What your partner and your mentor will never do to the reasoning behind your next move
🔒 The devil’s advocate prompt that interrogates your decision one question at a time, then hands down a verdict
You’re about to say yes.
Maybe to the offer that landed this week. Maybe to the counteroffer your CEO slid across the table to keep you.
And everyone you’ve asked for advice agrees with you.
That should worry you.
Why this prompt exists
The 18-month number
The success rate for executives at the 18-month mark in a new role sits between 40 and 60%.
Turn that around: 40 to 60% of executives fail within 18 months of signing. For a decision worth $200k to $400k a year, those are coin-toss odds.
I run retained executive searches for a living. I’ve watched strong candidates take roles their whole circle applauded. The applause never shows up in the 18-month number.
Your advisors won’t do this job
By the time you ask for advice, you’ve usually already decided. You’re collecting votes.
And your circle knows how to vote. Your partner wants you happy. Your mentor enjoys being agreed with.
Nobody in that room is paid to find the crack in your reasoning.
AI does this job without flinching. It has no stake in your outcome and no relationship to protect. Ask it to argue against you and it will keep going for as long as you can stand it.
That’s this week’s prompt. It interrogates your career decision before you make it, then tells you where the reasoning breaks. Built for Director, VP, and C-level decisions: offers, exits, pivots, counteroffers, relocation, going independent.
If your decision survives the interrogation, sign with confidence. If it breaks, you found out for free.
How to use it
1. Copy the full prompt below into Claude or ChatGPT.
2. Answer one question at a time. Give real numbers. Vague answers get you a vague verdict.
3. Let it finish. It interviews you first. The attack and the verdict come at the end.
The prompt
