executive-mentor

Name: executive-mentor
Availability: InStock
Author: jmigrala

Critique strategic plans with adversarial reasoning workflows for executives.

Updated Oct 30, 2025

Search Tags:#postmortem #decision-framework #risk-analysis #pre-mortem #adversarial-thinking #board-prep #executive-coaching

Ready to run

npx skills add https://github.com/jmigrala/priceyourfence --skill executive-mentor-jmigrala

💬 Prompt for ChatGPT / Claude Chat▼

Please help me install this Agent Skill.
Skill: executive-mentor
Source: https://github.com/jmigrala/priceyourfence/tree/main/.agents/skills/executive-mentor
Command: npx skills add https://github.com/jmigrala/priceyourfence --skill executive-mentor-jmigrala

SYSTEM DOCUMENTATION & REQUIREMENTS

💡 This Skill includes scripts (resource) and references (resource) components.

What problem does it solve?

Adversarial thinking partner for founders and executives. It stress-tests plans, prepares for brutal board meetings, dissects decisions with no good options, and forces honest post-mortems to surface holes before the board notices.

Core Features & Use Cases

Adversarial review: surface holes in plans before execution.
Board-prep and crisis planning: generate hard questions, risk assessments, and playbooks.
Decision support: run structured challenges (pre-mortems, stress tests, postmortems) to improve outcomes.

Quick Start

Ask it to run an adversarial review of your current plan by simulating a board discussion and a postmortem.

Frequently Asked Questions about executive-mentor

High-intent search queries and answers about installing and using this skill.

FAQPage Schema

How do I run a pre-mortem to surface hidden risks in a strategic plan?▼

A pre-mortem stress-tests strategic plans by applying adversarial reasoning workflows that simulate failure scenarios before execution. It generates hard questions and risk assessments to surface hidden holes in your plan, ensuring weaknesses are identified and addressed proactively.

What is adversarial thinking and how does it apply to executive decision-making?▼

Adversarial thinking in executive decision-making involves applying structured critique to strategic plans to surface hidden risks. It works by challenging assumptions through pre-mortems, stress tests, and postmortems, forcing honest evaluation of decisions to improve outcomes before boards or stakeholders notice flaws.

How do I prepare for a brutal board meeting with risk assessments and playbooks?▼

You prepare for brutal board meetings by running adversarial board-prep workflows that generate hard questions, risk assessments, and crisis playbooks. This process stress-tests your strategic plan against potential board critiques, ensuring you anticipate difficult questions and have documented responses ready for discussion.

Can I use a decision matrix scorer and stakeholder mapper for crisis management?▼

Yes, you can use Python tools like decision_matrix_scorer.py and stakeholder_mapper.py during crisis management and stress-testing. These tools support adversarial reasoning workflows by quantifying decision trade-offs and mapping stakeholder impacts, which helps leaders navigate decisions with no good options.

What is the best way to conduct a postmortem that forces honest evaluation of decisions?▼

The best way to conduct a postmortem that forces honest evaluation is to apply structured adversarial critique workflows. By running a dedicated postmortem command, you dissect decisions with no good options, surface hidden risks that were missed, and generate an honest assessment of what went wrong to improve future outcomes.

When should I use adversarial review instead of standard risk analysis for strategic plans?▼

You should use adversarial review instead of standard risk analysis when preparing for board meetings, making hard calls, or managing crises where hidden risks must be surfaced. Adversarial thinking actively challenges plans through pre-mortems and stress tests, whereas standard analysis often only catalogs known risks without testing underlying assumptions.