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One Question

Each week I ask one question and try to answer it.

"Is micromanagement back in fashion?"

4 min read

Jul 14, 2026

"Is micromanagement back in fashion?"

Welcome to this edition of "One Question". "Is micromanagement back in fashion?" I recently had to put one of my AI agents on a PIP (performance improvement plan).... sort of. Maybe I've fired him? Maybe I just moved him to the agent equivalent of Storage B. (Office Space reference) My relationship with my agent, who I named Walter, started off beautifully. It’s been rocky ever since. Here's the story of Walter. First, what's an agent? Using ChatGPT or any of the others is like buying a car...

Is anyone working less?

3 min read

May 12, 2026

Is anyone working less?

Welcome to this edition of "One Question"! A ridiculous AI generated image showing the same person twice. Unless they are twins? Who work at the same place? And wear the same outfits? At least they don't have six fingers. Is anyone working less? Seventeen years ago, Tim Ferriss wrote The 4-Hour Workweek. He talked about working smarter, automating the mundane, and freeing yourself from the grind. The book became the blueprint for people who didn't want to wait until retirement to live the...

"Are we there yet?"

3 min read

Apr 21, 2026

"Are we there yet?"

Welcome to this edition of "One Question". At the bottom I have a link to a short feedback form. I'd love to learn what you think about my newsletter. AI generated "Are we there yet?" kid "Are we there yet?" Picture this. You're driving a car. You're 30 minutes into a three-hour trip. You have a fresh cup of coffee sitting in the cup holder next to you. Traffic is moving well. All of a sudden, the six-year-old sitting in the back seat blurts out, "Are we there yet?" You glance at the GPS and...

Are we all turning into LeBron James?

2 min read

Apr 7, 2026

Are we all turning into LeBron James?

Are we all turning into LeBron James? I recently attended a conference called Transform. Great conference. I highly recommend! The attendees were primarily Chief Human Resources Officers and Chief Learning & Development Officers. There was also a new title held by some, “The Chief Human Resources and AI Enablement Officer”. The fact that this new title exists is a reflection of the time we're in. The rollout of new technologies inside companies has generally fallen under the umbrella of the...

Does your job from ten years ago exist today?

3 min read

Mar 12, 2026

Does your job from ten years ago exist today?

I have a big personal announcement, but I’ll leave it to the end so you can read this newsletter first. Does your job from ten years ago exist today? My first job out of college was at Book of the Month Club. Internally, we called it BOMC (pronounced Bomb-See). At the time, BOMC was primarily a print catalog. My job was to wander around the building gathering all the assets for each month's catalog - book covers, copy, layouts, etc. There were catalogs for different genres, and the pressure...

What do brainstorming and tequila shots have in common?

3 min read

Feb 26, 2026

What do brainstorming and tequila shots have in common?

Before you dive into this newsletter, I have BIG NEWS. I'm launching a startup focused on helping companies with AI literacy. It's the biggest challenge I hear from clients. It's so big that it's worth doing something big about it - bigger than my existing business. More to come, but I'd love to hear if and how this is a challenge for you. And now... the newsletter. What do brainstorming and tequila shots have in common? I’m sure you’ve attended a few brainstorming meetings in your career. To...

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