I Asked AI to Challenge Two Decisions.
Here’s What Happened. Raising the Barr Weekly Memo: Issue 717

Last week, I shared how I built an AI Skill that helps me sharpen my content creation, challenge ideas, uncover deeper insights, and strengthen what I publish. It has become a powerful part of my creative process.

This week, I created a different Skill and put it to work on two decisions that mattered to me. One involved expanding my AI Insider Lab. The other concerned strengthening leadership in a photography organization I lead.

Both experiences reinforced the value of AI as a trusted thinking partner. Through thoughtful dialogue, challenging questions, and a willingness to question each other’s reasoning, we can discover possibilities and approaches we might otherwise overlook.

Expanding the AI Insider Lab

I’ve been committed to expanding the AI Insider Lab and welcoming additional groups of professionals who want to apply AI meaningfully in their businesses. That commitment hasn’t changed. What I wanted to examine was how best to approach the next group, including the program’s structure, learning experience, and execution strategy.

I used a six step process called Adversarial Decision Testing. Its real value comes from the dialogue. AI questions my assumptions, introduces considerations I hadn’t anticipated, and challenges my reasoning. Equally important, I question its recommendations, defend my thinking, and redirect the discussion when necessary.

What surprised me was where that conversation led.

I began by examining how to prepare for the next group. During the discussion, I raised a question I hadn’t intended to explore: Should the AI Insider Lab remain a 12 month program, or would six months serve members better?

That opened a much deeper examination of the learning experience. A shorter program might sound appealing, but would compressing the material actually improve results? Or would it create greater pressure to absorb and implement everything?

The discussion helped me recognize that the real question wasn’t simply how long the program should run. It was how to give members sufficient time to learn, experiment, and apply what they discover.

I haven’t finalized every element of the next group’s structure, but the examination strengthened my understanding of what a meaningful learning experience requires.

Strengthening Leadership Beyond Myself

As president of the Chagrin Valley Camera Club, I’m committed to developing stronger leadership that supports our vision and prepares future generations to guide the organization.

I brought this challenge into the same decision testing process. This time, we examined delegation, accountability, shared responsibilities, and how to build an organization that doesn’t depend excessively on its president.

At one point, AI asked whether I would be willing to leave certain activities temporarily unorganized if nobody accepted responsibility, rather than assume the work myself.

My answer was clear. I already carry substantial responsibilities within the club, and taking on more would undermine the leadership development I’m trying to encourage.

The question didn’t change my conviction, but it helped clarify an important boundary. We then explored how responsibilities could be shared, how members could exercise greater independence, and what accountability would look like.

I also challenged AI when its recommendations extended too far into future succession planning. My immediate priority was strengthening leadership for the current year while continuing to develop the organization’s longer term future.

The result was more than a decision. It was a clearer approach to achieving the outcome I wanted, including responsibilities, boundaries, and practical next steps.

What the Two Experiences Revealed

Both examinations reinforced three important lessons:

1. Challenge your assumptions, not just your conclusions. An alternative you haven’t considered may reveal a better approach or strengthen your original thinking.
2. Examine what success actually requires. Clarify the responsibilities, conditions, and actions necessary to achieve the intended outcome.
3. Challenge AI in return. A trusted thinking partner should welcome questions, disagreement, and correction. Your expertise and judgment remain essential.

What impressed me most was how the dialogue moved beyond evaluating decisions toward developing more thoughtful approaches to implementing them.

From a Workflow to a Skill at My Fingertips

Adversarial Decision Testing began as a structured workflow I designed and created for my own use and for members of the AI Insider Lab.

Turning that workflow into an AI Skill took the experience further. The Skill now guides the examination through six stages, asks questions one at a time, responds to my reasoning, and helps develop practical conclusions and next steps.

I now have another tool at my fingertips whenever I want to challenge an assumption, explore alternatives, reconsider an approach, or strengthen my thinking about a business or personal challenge.

My personal library of AI Skills has grown significantly, alongside the applications we’ve been developing. Let me ask you this: What if you could turn the business and personal challenges you face into practical, reusable solutions that are ready whenever you need them?

These aren’t merely experiments. AI has become a powerful tool for rapidly developing practical solutions and putting them to work.

AI Insider Lab members are beginning to use these Skills and develop their own. This week, they’re receiving Adversarial Decision Testing for both ChatGPT and Claude, which they can use, customize, and enhance as their capabilities grow.

At The Chad Barr Group, we’re also exploring opportunities to bring more of our AI Skills and applications to market, including developing customized solutions for clients. Stay tuned for what’s coming.

Try It With Your Next Decision

You don’t need a specialized Skill to begin. Choose a decision you’ve already made or are considering, and give ChatGPT or Claude this prompt:

I’m going to share a decision I’ve made or am considering. Don’t automatically agree with me or immediately recommend a solution. Act as a rigorous thinking partner. Challenge my assumptions, identify weaknesses in my reasoning, explore meaningful alternatives, and help me recognize what I may be overlooking.

Ask one question at a time and wait for my response. Welcome my challenges to your reasoning. Help me clarify what success requires, including responsibilities, conditions, and practical next steps. Keep the final decision in my hands.

This simple exercise may reveal something you hadn’t considered. The complete Skill takes the experience further, but the essential principle remains: better thinking emerges through thoughtful dialogue, not simply better answers.

I’m also preparing to welcome another group into the AI Insider Lab. More details will follow soon.

Challenging a decision isn’t always about changing your mind. Sometimes it’s about discovering what your decision will require to succeed.

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I Asked AI to Challenge Two Decisions. Here’s What Happened.