Writing on AI, leadership, and the work itself.
Field notes from rebuilding a business on AI, and from helping founders build an AI team inside their own companies.
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Prompt Engineering vs Context Engineering: What a Business Owner Needs to Know
Prompt engineering is how you word the ask. Context engineering is what the AI knows when you ask. What to check when an AI answer comes back weak, and a two-question check to run before you type.
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What Do You Say to a Team That's Afraid of AI?
Executive coach Julia LeFevre on what sits under your team's fear of AI, why logic doesn't reach it, and the words a leader can use instead.
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Podcast
Why Facts Won't Calm Your Team's AI Fear
Executive coach Julia LeFevre and I talk about what sits under your team's fear of AI, why facts and training won't calm it, what leaders can do instead, and why AI made good enough easy.
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Automate or Augment? A Job-by-Job Test for Small Business Owners
Should you automate a job or augment the person doing it? Run four yes/no questions on one job at a time. Some jobs should be automated. The rest get AI in a supporting role, like a reviewer.
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Podcast
Your Team Found an AI Workaround. Is It the Fix?
John Matoso and I talk about why a policy and a training module won't hold on their own, what AI literacy looks like at work, and whether your team's AI workaround is something to shut down or learn from.
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Two Ways to Hand AI Too Much
People hand AI too much in two ways: access to their email, files and CRM, and the thinking itself. This week's PHP emergency shows the first. A reviewer role for AI helps with the second. Here is how a 5 to 50 person firm sets limits on both.
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Podcast
You Bought the AI Tool. Did Anyone Teach Your Team to Use It?
John Matoso and I talked about why owners keep buying AI tools and skipping the training, why how do I prompt it is the wrong question now, and whether being rude to Claude says something about how you lead.
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Why Do AI Pilots Stall After the Demo?
Most AI pilots in a 5 to 50 person firm stall for reasons that have little to do with what the tool can do. Nobody owns the first job, and nobody said what 'used' means. Here is a smaller start that holds: one job, one owner, one week-two test.
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Podcast
Don't Do AI to People
John Matoso and I talked through AI adoption as a human change. He wants the people who do the work in the room before anyone redraws it. I still want a quick win on a workflow they already have, so the trust shows up before the redesign.
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You Told Them to Use AI. Nobody Bought the Account.
You encouraged adoption and it worked. The work is now happening in personal accounts your organization does not own, under vendor terms nobody in the building has read. Here is what those terms actually say, checked this week, and the smallest fix that holds.
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Your Website Is a Business Card
A referred client trusted me before our first call. Where website credibility fits, and how I now write regularly from calls and notes I already had.
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Start With Meeting Prep, and the Follow-Up You Keep Dropping
The first AI job a founder should hand over is meeting prep and the follow-up loop after it. Not because meetings are special, but because that prep is work you already do badly under pressure and the follow-up is a loop you already drop.
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Your Team Is Hiding It, and Your No Is Why
The hidden AI use inside your company usually starts with a leader saying no. The tool gets used anyway, and the refusal only decides whether you hear about it.
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The Vacation You Never Actually Take
Most founders already know the fix for bad handoffs. Here's why knowing it has never been enough.
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The Genie Problem Doesn't Stay on One Desk
A genie doesn't misunderstand your wish. It grants it exactly. Now put that genie in front of your whole company, and the wish gets granted before anyone catches that the ask was wrong.
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You Sent the AI Memo. Your Org Chart Didn't Move.
Every founder who rolled out ChatGPT seats can name the tool. Almost none can name the seat it replaced. Here's the test that catches the gap before your next job req does.
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AI Is a Tool, Not a Genie
The machine did exactly what I asked and the result was unusable. That's not a bug in the tool. It's the oldest story we have about getting what you asked for, and it's the reason your people can't leave the room.
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The Stoic Case for AI Adoption
Every founder thinks this is the most disruptive moment business has ever seen. The Stoics say the panic is optional. Your response is the only lever you have.
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Tools Aren't Strategies
The question founders ask me most is which AI tool to use. It's the wrong first question. A tool is a part, not a strategy. Here's the durable layer to build instead, so the next tool is something you plug in, not something you rebuild around.
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AI Didn't Get Too Expensive. We Deployed It Like Idiots.
The AI bill came due at Meta and Microsoft. The tech didn't fail, the rollout did. Four mistakes that made AI cost more than the people it replaced, and the fix.
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I Had a Frontier Model for a Week. I Used It to Audit My Own Systems.
I had Anthropic's Fable 5 for a short window. Instead of building more, I pointed it at my own systems. The model is 10 to 20 percent of the work. The system it plugs into is what survives the swap.
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The Second Desk: The AI Team I Built Because My Ideas Kept Dying in the Handoff
Working Genius named the exact gap I'd had for years. No genius in Tenacity or Galvanizing. So I built an AI team to close it. This is what that looks like.
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Everyone's Job, Nobody's Job: What I Keep Turning Over After Watching a Product Exec Rebuild Her Company
A product exec rebuilt her company around AI in the open. Here's what stuck, and the one thing I'd push back on: the tools are not what make AI pay off. Your people are.
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Why Your AI Rollout Is Failing (It's Not the Tech)
Most AI initiatives don't fail on the technology. They fail because nobody changed how they work on Monday. AI adoption is a leadership problem wearing an IT costume.
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What AI Can't Do Is the Whole Point
Automation replaces people. Augmentation multiplies them. Eight months ago I rebuilt my own business on an AI team, and the part that worked was the part AI never touched.
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AI Vendor Risk Is a CAIO Decision, Not an IT Ticket
If your operation runs on one remote AI model, that vendor is a continuity risk. Here is how to own the ground your business stands on.