I asked AI to improve one paragraph in my profile instructions. The proposed replacement addressed the requested change and dropped three requirements I had already approved. I then realized that the requested change can be correct while the overall result is wrong. The revision had removed safeguards I had already established for how AI should work with me. I caught the omissions and had those instructions restored. These were standing instructions intended to guide future conversations. Had I copied the...

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...

I want more from AI than a fast answer. I want a thinking partner that questions my assumptions, challenges my conclusions, and tells me when my reasoning falls short. I challenge its answers just as firmly, because confidence is not proof that either of us is right. But a productive exchange has value beyond the work in front of me. When a question exposes a weak argument or a correction improves the result, I want that lesson carried into the...

The default AI request I hear constantly is: “Write this for me.” People hand AI an unfinished idea and ask it to make the idea sound finished. The result can be polished and persuasive long before the thinking is ready. AI can make an unfinished idea sound like a finished conclusion. That is the wrong sequence. AI has not earned the right to write. First, it should interview you until your idea is strong enough to publish. The Article I...

For years, I have said that a brilliant answer to the wrong question is still worthless. That was true long before AI. It matters even more now because AI can produce an answer so quickly, confidently, and professionally that we may never stop to ask whether it solved the right problem. A weak prompt can produce a meaningless answer. A poorly defined business problem can produce something more dangerous: a polished skill that repeatedly solves the wrong thing. The Question...

This week’s Raising the Barr is intentionally different. In the spirit of Rosh Hashanah, I am sharing one article without the usual carousel or video, leaving more room for reflection. For most of my life, reflection was a private meeting between me and myself. I never questioned the obvious conflict of interest. I was the person under examination, but I also controlled the questions. I presented the evidence, explained the circumstances, defended my decisions, and delivered the verdict. That arrangement...

Last week I did something in a live AI Insider Lab session that I could not rehearse, could not edit, and could not rescue if it went badly. I put a real business on the screen in front of a room of experienced consultants and let AI take its marketing plan apart. Patrick and Barbara Lyons volunteered: Barbara Lyons Mulvey Interiors. Barbara has spent twelve years in interior design. She is a color expert, and she can walk into a...

Last week I told you I would settle one question live, in front of a room, and report back today. The question was whether the AI Insider Lab is the umbrella over everything I do or one of the pieces underneath it. I named a second question behind it, about pricing and what a client actually thinks they are buying. The first question did not get settled during the live session. The second one broke wide open instead. I went...

This issue does not end with an answer. That is deliberate. For more than thirteen years I have arrived in your inbox with a position. Something I had already worked out, tested, and was prepared to defend. This week I am arriving with a decision that is wide open, and tomorrow afternoon I am going to work it in front of a room of people with AI arguing against me the entire way. Start with what I told you last...

AI will agree with you. Ask it for feedback, a second opinion, a pressure test on your best idea, and the first thing back is some version of yes. Good thinking. Strong point. You are on the right track. That is not the AI being honest. It is the AI being built. Standard models learn from human feedback, and human feedback rewards the answer that pleases. Agreement scores well. Disagreement feels like friction, so training optimizes it out. There is...