Are you leading with an AI-first approach? Are you and your teams using AI as a tool?

Or, is it people-first, AI-forward? Or are you guiding AI as teammates?

Words matter. Tom Winter and I will unpack this on Wed, May 21 at noon ET / 9 am PT. Come join us!

https://lnkd.in/gCP4Kfqq

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By day, I advise on AI and GTM strategy. By night, I fought a box cutter, a glue gun… and proved a point AI still can’t touch.

This week, I ran a little experiment.

I designed a graduation box for my daughter and also asked AI to generate one too. Something beautiful. Something meaningful.

And honestly, AI did a solid job (right photo). Clean, polished, visually striking.

But here’s what it didn’t do:

► Stay up late with a box cutter

► Burn its finger on a hot glue gun

► Get the warmest hug and biggest smile when my daughter saw it

► Hear her friends say, “That’s the cutest graduation box I’ve ever seen”

► Watch people pause to leave sweet, heartfelt notes inside

We wrapped it up with the most incredible graduation party at home with 120+ of our dearest family and friends came together to celebrate her.

And now, she’s counting down the days until she becomes a proud CU Buff at the University of Colorado Boulder.

This whole moment reminded me that marketing isn’t arts and crafts. But it lives at the intersection of strategy, creativity, and human connection.

AI can assist, accelerate, and even inspire. But it can’t copy love, laughter, or the pride in creating something with your own hands.

It can’t recreate something so imperfect but so perfect for the moment.

Will AI ever replace that?

Maybe it’ll match the look and feel. But the memory, the meaning, the human in it all?

That’s still ours.

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What if AI isn’t just changing how we work but quietly breaking the way we’ve organized companies for decades?

The walls between departments are blurring. Customers don’t care about your org chart. They expect seamless experiences, fast handoffs, and connected journeys.

That’s why a new operating model is emerging: work charts.

Where org charts define who knows what (departments + roles), work charts define what needs doing (jobs-to-be-done + workflows).

This shift is already happening faster than many leaders realize.

In this week’s newsletter, I share:

• The AI Work Chart Maturity Model I use with clients to map their evolution (a model aligned with Microsoft’s Work Trend Index Report and Harvard + P&G study)

• Real-world case studies from Dice and Cin7 showing early wins and lessons

• Practical steps you can take right now to start breaking silos in your org

You can read the full issue below.

Prefer to listen instead? There’s also a 12-min podcast version with two AI hosts. Listen to it while having lunch, walking the dog, or driving. Link is in the comments, https://lnkd.in/gUysN2E6.

This is part of my biweekly Practical AI in GTM newsletter. I share real-world applications and strategic insights for forward-thinking teams. You can subscribe at the top of the page if you want these in your inbox every other week.

A huge thank you to Scott Braun (SimpliSafe), Carol-Lyn Jardine (Dice/DHI Group Inc), Sean McCaffrey (Cin7), and Jacob Warwick (ThinkWarwick Global). It’s been an absolute pleasure to go on this AI journey with you and your teams.

Here’s the 12-min AI podcast version of this newsletter. Listen to it during lunch, while driving, walking the dog 😉 https://drive.google.com/file/d/1nw2RaTGn47ihf-2gl0Yqqb2r7C_BrZtp/view?usp=sharing

Once you hit play, give it just a few seconds then it will start.

Disclaimer: This podcast was generated by AI based on this written newsletter and reviewed by me to ensure ethical and responsible AI use. It’s designed to provide an efficient, more inclusive way to consume information.

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