mentor-cunningham

Apply Cunningham's frameworks to slow impulsive business decisions.

3|1|Updated Mar 27, 2026

Search Tags:#frameworks #coaching #risk-management #mentorship #decision-making #critical-thinking #business-strategy

Ready to run

npx skills add https://github.com/ryankolean/summit-claude-skills --skill mentor-cunningham

💬 Prompt for ChatGPT / Claude Chat▼

Please help me install this Agent Skill.
Skill: mentor-cunningham
Source: https://github.com/ryankolean/summit-claude-skills/tree/main/skills/mentor-cunningham
Command: npx skills add https://github.com/ryankolean/summit-claude-skills --skill mentor-cunningham

SYSTEM DOCUMENTATION & REQUIREMENTS

What problem does it solve?

Coaching through Keith Cunningham's published frameworks to help users slow down, think critically about business decisions, avoid costly mistakes, and ask better questions.

Core Features & Use Cases

Thinking Time: Guided time for deliberate analysis before acting.
Dumb Tax & Question Quality: Aid in reframing questions to surface risks and learning from past mistakes.
The Constraint: Help identify the single limiting factor that, if addressed, unlocks growth.
Use Case: A founder evaluating a new initiative pauses to map questions, risks, and expected outcomes before committing resources.

Quick Start

Ask Cunningham to enter Thinking Time mode and walk through a current business decision using his core frameworks.

Frequently Asked Questions about mentor-cunningham

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

FAQPage Schema

How do I slow down impulsive business decisions before committing resources?▼

To slow down impulsive business decisions, you apply guided Thinking Time frameworks that force deliberate analysis, mapping risks, and evaluating expected outcomes before making strategic commitments.

What is the best way to identify the limiting factor blocking my business growth?▼

To identify the limiting factor blocking business growth, you find the constraint by isolating the single bottleneck that, if addressed directly, unlocks further operational scale and revenue.

How do I ask better questions to surface hidden risks in my strategy?▼

You ask better questions to surface hidden risks by applying the principle that the quality of your answers is determined by the quality of your questions, using the Unasked Question framework to reframe problems.

Can I use this coaching framework for evaluating new startup initiatives?▼

Yes, you can use this decision coaching framework for evaluating new startup initiatives. It is designed for founders who must decide on bets, commitments, or strategic moves to avoid paying a Dumb Tax on mistakes.

What is the difference between revenue, profit, and cash when making strategic bets?▼

When making strategic bets, the difference is framed as Revenue Is Vanity, Profit Is Sanity, Cash Is King, prioritizing actual cash flow and profit sustainability over top-line revenue metrics.

When should I not use a deliberate thinking process for business strategy?▼

You should not use a deliberate thinking process for business strategy when facing routine, low-stakes operational choices that require immediate execution, as the Thinking Time framework introduces necessary friction for high-stakes decisions only.