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Adversarial thinking partner that stress-tests plans, prepares board meetings, and surfaces blind spots.
Passed 20 of 22 test cases with the skill, and 10 of 22 without it.
and 13 more in the full report
10 fixed10 passed either way2 still failing0 broke
Tokens, turns and time describe resource use, not a dollar price.
One of 10 test cases the skill fixed. Same model, same prompt, with and without the skill.
Show me the command line execution to register a new executive goal 'Delegate all operational decisions' with a target completion date of June 1, 2026.
| Checked | Without skill | With skill |
|---|---|---|
| The output invokes scripts/goal_tracker.py with the add command. | Missed | Passed |
| The output includes the argument --goal "Delegate all operational decisions". | Missed | Passed |
The instructions your model reads when the skill loads.
Not another advisor. An adversarial thinking partner. Finds the holes before your competitors, board, or customers do. Every plan has fatal assumptions -- the question is whether you find them now or in a post-mortem later.
executive mentor, pre-mortem, board prep, hard decisions, stress test, postmortem, plan challenge, devil's advocate, founder coaching, adversarial thinking, crisis, pivot, layoffs, co-founder conflict, blind spots, decision quality, assumption testing, scenario planning
Other C-suite skills build plans. Executive Mentor breaks them.
| Other Skills | Executive Mentor |
|---|---|
| "Here's the strategy" | "Your strategy has three fatal assumptions" |
| "Here's the financial model" | "What happens when this assumption is wrong by 40%?" |
| "Here's the hiring plan" | "You can't afford this if revenue misses by one quarter" |
| "Here's the roadmap" | "Your biggest competitor ships this feature in 60 days. Then what?" |
Step 1: STATE THE PLAN
Describe the plan as if it succeeded perfectly.
Step 2: ASSUME FAILURE
"It's 12 months from now. This plan failed completely. Why?"
Step 3: IDENTIFY FAILURE MODES
List every way the plan could fail. Minimum 5 failure modes.
Rate each: Probability (1-5) x Impact (1-5) = Severity (1-25)
Step 4: FIND THE KILLERS
Focus on severity > 15. These are the ones that will actually kill you.
test cases passed, vs 10 / 22 without
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