The AI Sparring Partner: Using AI Prompting to Think Critically

Course details

Most people use AI to get answers faster. Justin Shaifer teaches business professionals to use it to think better. In this course, Justin explains why AI tools are built to agree with you, what that quietly costs you and your team, and how to set up a conversation where AI argues back instead of nodding along. He covers loading real context, configuring tools to challenge you by default, directing AI research, verifying AI output, and running full sparring sessions on real work. Every technique is demonstrated across AI tools (including Claude and ChatGPT), so the skill travels with you no matter which tool you use. After finishing this course, you will have built a personal library of sparring prompts you can run against any future project.

Learning objectives
Explain why AI tools tend to agree with you and how that agreement weakens your thinking.
Set up an AI conversation that challenges your reasoning instead of confirming it.
Configure AI tools so they push back on your ideas by default.
Direct an AI research task and verify whether the sources it cites actually support its claims.
Run a complete sparring session on your own decks, messages, and decisions.

Concepts

The AI Yes-Man Problem

Meet your AI sparring partner
Why AI agrees with you and what that costs

Turn AI Into a Worthy Opponent

Add your unique context
Give AI a role with a stake in disagreeing
Make AI interview you before it answers

Make It Argue Back

Set it once - Tune your AI to push back
Run a premortem - Assume AI already failed
Pressure-test a strategy doc from start to finish

Put AI to Work as Your Researcher

What deep research does
Check the sources AI gave you

Spar Across Your Real Work

Stress-test a deck before you present it
Sharpen high-stakes written communication

Conclusion

Keeping your judgment sharp