Later Never Comes What I saw driving past my childhood home this morning. They say you can’t go home again. First of all, I don’t know who “they” are. But in this case, “they” weren’t wrong. My mother-in-law was visiting last week. This morning I drove her to the bus station so she could head […]
In this week’s Data Diaries, we follow last week’s data-boundary thread into the harder question: what happens when the model remembers a person it should forget, and who answers for the decisions that model then makes? Privacy and automated decisions sit on the same fault line, and the law now treats them that way. Here […]
Before You Scale, Land It Once The fastest path to everywhere goes through one place. Your AI strategy looks ambitious. That is the problem. I say that to almost every leader I talk to right now, because the roadmap is impressive on paper and producing very little in reality. The plan covers six departments. The […]
INBOX INSIGHTS: (2026-08-26) Walking Back Productivity, Vibe Coding Part 4 :: View in browser 👉 Take our new course, AI for Writers! Watch This Newsletter 🎧 Listen to this newsletter as an MP3 How do you walk back your productivity? You would think that our pipeline or payroll is what keeps me up at night. […]
Read More… from INBOX INSIGHTS: (2026-08-26) Walking Back Productivity, Vibe Coding Part 4
You’re Not Stuck in AI Pilot Purgatory. You’re Hiding In It. A pilot is not a commitment, and that is the whole problem. You haven’t been stuck in pilot purgatory. You have been hiding in it. I want to say that as plainly as I can. The pilots are not the problem. Most of them […]
A Realistic 90-Day AI Plan This is the last issue in the series. Thank you for sticking with me through the last three pieces. You’ve learned more about the unglamorous side of AI work than most in our field are willing to share. That matters. Quick recap of where we’ve been: Issue 1: The gap isn’t […]
You’re Starting in the Wrong Place Last week I wrote about the gap between having an AI strategy and actually doing anything with it. The response was a lot of variations on the same email: “Yes. This is us. Now what?” So let’s get into it. Let’s begin with the most common mistake I see. […]
This post was originally featured in the March 25th, 2026 newsletter found here: INBOX INSIGHTS: Directing AI, AI Digital Clone Part 1 Moving from Executing to Directing AI If you know me, you know I have opinions about AI replacing people. Strong ones. Loud ones. The kind that earns me the “ranty pants” label on […]
This post was originally featured in the March 11th, 2026 newsletter found here: INBOX INSIGHTS: 5P Framework by Trust Insights™, B2B Marketing Writing and AI Part 1 (Re)Introducing the 5P Framework by Trust Insights™ I have a confession: I used to think the problem with change management was that people didn’t follow the framework closely […]
Why We Plan, But Don’t Execute Let me ask you something, and I want you to be honest with yourself: How closely are you actually tracking that Q1 roadmap you sat through endless hours of meetings to put together? Are you planning without doing? I’ll wait. I posed this question to our free Slack community, […]
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