Born After AI: What a Company Founded Today Should Do Differently
Companies have born-on dates. AI just changed what yours should be. I’ve been thinking about a question lately: What would ...
The Hand-Me-Down Frontier
Also: At the end of this post over 25+ links, stories, and tools I found interesting in the world of ...
The Unwatched Hours
At the end of this edition of the Human Side of AI, over 30 stories, releases, and editorializing that caught ...
Do You Have to Do the Work to Understand It?
AI is changing what we can direct. How should that change what we have to learn? ….At the bottom of ...
You Changed the Work. You Didn’t Change the Test
At the bottom of this post: 25+ links to stories, launches, and perspectives on AI I think are worthy of ...
Yes, I Used AI. Call It a Cheat. The Story Is Still Mine.
At the bottom of this post: 37 links to stories, launches, and perspectives on AI I think are worthy of ...
Every Room Is an Open-Book Room Now
A job candidate can now read the answer to your hardest interview question off the inside of their own glasses. ...
You Lack Judgement
Get a knowledge point wrong and most of us are fine. You thought company X did Y. You got yesterday’s ...
Writing Couldn’t Answer Back. AI Can.
We’ve entered the detection wars. Substack’s launch post in July noted that Pangram can detect whether AI was used but ...
Working On a Business You’ve Never Worked In
The person who handles the finances in our business never had formal training for it. They’d tell you themselves they’re ...
AI Made These Skills Valuable. You Can’t Cram For Them.
A manager put the problem to me plainly a few weeks ago. “Can they actually get there, or am I ...
The Usage Mirage: Why Atlassian Handed AI to the Business Instead of IT and Why a Multitude of Models Matter
Atlassian just published an honest report about their own AI transformation, including what hasn’t worked. One number in it should ...
Your AI Rollout Is Going Great. Just Ask Your Boss
I spend a lot of time asking leaders and employees the same questions about AI, and I keep getting answers ...
The Redesign Divide: Everyone Has the Tools. Only 16% Changed the Work.
There’s a test you can run on any company in about five minutes, and it predicts more about their AI ...
If You Tried AI 90 Days Ago, You Haven’t Tried AI
Best before: 90 days. That’s the expiration date I’d put on almost any strong opinion you hold about what AI ...
The Three Humans: Evaluating Hires, Promotions, and Vendors When AI Makes Everyone Look Expert
What are you even evaluating anymore? My day to day involves two roles. For the first, it involves being the ...
The Legibility Gap: Your AI Isn’t Underpowered, It’s Under-Onboarded
Try this test. Could an AI agent do an hour of useful work for you tonight, while you sleep? Not ...
The Coupon Trap: Why “With-AI / Without-AI” Pricing Quietly Devalues Your Firm
A research agency just rolled out two-price proposals: one number with AI, one without. AI saves time, so they pass ...
You’re Going to Be Packaged. You Might As Well Go First
I had a back-and-forth on LinkedIn last week that has stayed top of mind for me. Someone argued that students wearing ...
The Inbox Mirror
Everyone asks me the same question in AI training. What should I build first? Custom GPT, skill, workflow, agent, vibe-coded ...
Peacetime Is Over. Most of Us Haven’t Realized It Yet
There’s a newspaper ad from the late 1980s that ran in the Phoenix classifieds. “You Can Be The Voice of ...
Everyone is a Director Now: Taste and Judgment Beat Production in the AI Era
For two years the argument about AI writing has been stuck on one question. Did you really write it? Does ...
One-Way Authenticity
A client sent over a contract last week and I needed to review the terms in the agreement. I have ...
The 26-to-2 Conversation
A while back I watched a CEO on video describe, with visible excitement, how a team went from 26 people ...
The Visual Self: Why Every Leader Will Soon Need a Personal Visual Style, Not Just a Written One
For 25+ years of running businesses, I’ve worked on developing a writing style. A way of opening an email. A ...
The Forgiveness Gap
I see it almost every week. Someone posts a screenshot of an AI getting a citation wrong and racks up ...
The Great Downgrade
For the first time in nearly 30 years, I downgraded our Microsoft licenses last week. Not cancelled, just downgraded. The ...
The Art of Asking: Turning AI License Spend Into Actual Productivity
If you’re on a leadership team, here’s a question worth sitting with. You’re paying for ChatGPT licenses, Claude licenses, and ...
I Built an AI Board of Advisors. Here’s Why You Should Too.
One of the strategies I’ve been using for a significant amount of time is treating AI as a genuine thinking ...
Are You Skipping the Most Practical AI Step?
Today I want to talk about something that I think is really important to consider. If you’re a business leader ...
AI Made Your Team Faster…Your Performance Review Didn’t Keep Up
If you’re a manager whose team has meaningfully embraced Generative AI over the past year, you’ve obviously noticed a lot ...
RISE Above AI: A Framework for Knowing What to Keep and What to Give Away
I think we can all agree that AI is more than capable when it comes to taking on certain tasks ...
Are You a Good Delegator? Your AI Results Depend on It.
Does your manager delegate well? This is a question that most business professionals, if they have a manager can answer ...
The Era of Plausible AI
Today I want to talk about Moltbook and Moltbot. Now, there’s a lot I could say here about what this ...
The One Skill That Will Matter More as AI Takes Over
In 2026, there’s a skill I think you should develop. It’s the ability to debate well, and the reason I ...
Vibe Coding: Build Software for an Audience of One
As we move into 2026, I want to tell you something that I think you should be focused on all ...