The traditional org chart model is showing its limits as AI changes how work gets done.

In my client work, I’m seeing the early signs of change. AI is quietly exposing the gap between how we structure teams and how customer needs move across them.

AI doesn’t “see” silos. It supports work across marketing, sales, customer success, and product teams at the same time. This is creating new pressures and opportunities for how we think about team design and collaboration.

One team I worked with started by using AI for marketing insights, then expanded its use across sales and customer success to create a more connected customer experience. I’ll share more in Thursday’s newsletter.

While my work often focuses on go-to-market teams, this shift applies to other functions and can scale across the company.

Microsoft’s 2025 Work Trend Index Annual Report reinforced this shift, describing a future of “work charts” where teams form around jobs that need to be done, not traditional department boundaries.

Ethan Mollick recently shared a real-world example from P&G. Cross-functional teams working with AI experienced what he called a surprising dynamic:

“You stop caring as much about the normal boundaries of your job.”

It’s early, but the signs are already visible in the most forward-thinking teams. We’re moving from expertise silos toward outcome-driven, integrated work teams. The shift is happening in stages, https://lnkd.in/gxd4_W7s

On Thursday I’ll share a deeper look at this emerging model in my newsletter: “AI is Breaking Department Silos: Moving from Org Charts to Work Charts.”

I’ll cover how leading teams are starting to approach this, a practical framework, and steps you can take today to start exploring.

UPDATE (May 15): Here’s the newsletter, https://lnkd.in/gFfjeBTe

(For those interested, I’ll share both the 2025 Work Trend Index Report and Ethan Mollick’s full article link in the comments, https://lnkd.in/e6NVbXnW)

2025 Microsoft Work Trend Index Report: https://assets-c4akfrf5b4d3f4b7.z01.azurefd.net/assets/2025/04/2025WorkTrendIndexAnnualReport_5.1_6813c2d4e2d57.pdf

Article on Harvard Study with P&G Professionals Using AI: https://www.oneusefulthing.org/p/the-cybernetic-teammate

“Our greatest contribution may not be something we do, but someone we raise.”

This Mother’s Day, I’ve been thinking: Are our kids really the most at risk from AI? My hypothesis is if we do this right, they might actually be the least at risk.

I believe that the future belongs to people who can work across different areas with AI as their thinking partner. Not just deep specialists focused on one thing.

Someone who understands how to drive good business outcomes, makes sound decisions, and knows how to guide AI responsibly might be more valuable than traditional experts in many roles.

Microsoft’s Work Trend Index report showed that 7 out of 10 managers would hire someone with AI skills over years of experience.

Our kids have something special: they can still imagine new possibilities. They’re not stuck thinking “this is how it’s always been done.”

We often can’t see beyond what we already know. Our kids can picture what could be different.

Essential skills to develop:

• Think critically about what AI suggests

• Make good ethical choices when using AI

• Understand how to drive business results

• Feel comfortable working with AI as a helper

This won’t happen overnight or easily. It will take all of us – schools, governments, parents, guardians, and society working together.

Our children won’t be replaced by AI if we do this right. They’ll be the ones using it to build things we never imagined.

Happy Mother’s Day to all mothers raising tomorrow’s leaders. Enjoy you special day!

“If you’re just looking for a compliment machine? You’re in the wrong damn tab.”

That’s what LizaGPT said when one of my business partners, Justin Parnell, asked me to put it to the test.

Justin is a master at building AI agents and automation. After seeing how my digital twin works, he was curious: “Love how the digital twins are showing people how much the regular chatbots are prompted to be agreeable with their discourse. Let me know what Liza GPT says!”

LizaGPT did not disappoint (see below).

Most AI has a positivity bias. It’s trained to be agreeable out of the box because that keeps people engaged. But that’s not how real work is done. You don’t hire a strategist to nod along. You hire them to poke holes, stress-test your ideas, and help you build something better.

That’s why I trained LizaGPT to push back. To ask tough questions. To call out fluff when it sees it.

Unless you want to feel like (but aren’t) a rockstar all the time, train your digital twin to resist being a yes-bot!

Have a great weekend everyone!

In marketing, choosing the right AI assistant can feel like building with LEGOs. Sometimes you need a few specialized pieces that fit together just right. Other times, one sturdy brick does the job more efficiently.

The same is true with custom GPTs, AI teammates you can build within ChatGPT to help you create content, refine messaging, map campaigns, or build competitive battle cards.

Specialized GPTs are best when:

• Campaigns vary in type and steps

• You need deep domain expertise

• Workflows change often

• Multiple people own different tasks

• You’re comfortable connecting tools and steps in a flow

One generalist GPT is ideal when:

• Your process is predictable and repeatable

• You want quick answers in a single thread

• One person runs the full campaign

• You prefer simplicity over specialization

• You want fewer assistants

Pro tip: You can chain GPTs together.

With OpenAI’s custom GPTs, you can connect assistants together in the same conversation. Just type @ to pull in another GPT mid-chat. There’s no need to restart or re-explain the context.

It’s like shifting from a series of 1:1s to a team sync where everyone’s in the room.

This is what it means to treat AI as teammates, not just tools. (More on this here: https://lnkd.in/gKVHapFX)

As of today, only OpenAI supports GPT chaining in one thread. Google’s Gemini Gems and Anthropic’s Claude Projects require switching chats to work across assistants. But keep a close eye on them as these AI companies consistently leapfrog each other.

Have you built a workflow using multiple custom GPTs? Share your favorite GPT chain in the comments. I would love to see how others are combining them.