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Why CMOs Should Get Comfortable Being Confused By AI

A reminder that the fastest AI learners are not the leaders who pretend to know everything; they are the ones willing to wander, ask, and learn.
Drew Neisser

Drew Neisser is the founder of CMO Huddles and a globally recognized authority on B2B marketing. He’s an AdAge columnist, LinkedIn TopVoice, leading CMO coach, podcast host & friend of penguins everywhere.

Summary

At an AI conference, even seasoned CMOs can feel like they have wandered into a foreign country where they catch every third word. That discomfort is useful. The leaders who learn fastest are not the ones pretending fluency. They are the ones willing to wander, ask questions, and turn confusion into curiosity.

Why AI Rooms Can Make CMOs Feel Behind

It started in the opening keynote. AI as a five-layer cake. One of the layers? Inference.

Everyone around me nodded like this was Marketing 101, and I’m sitting there thinking, “Should I know this?”

That is the strange gift of being in a serious AI room right now. Even experienced leaders can feel behind. Acronyms fly. Vendors blur. Smart people say “model context protocol” with the same casual confidence most humans reserve for “lunch.”

There is something oddly powerful about putting yourself in a room where you do not speak the language. It is like traveling to a foreign country where you catch every third word and fill in the rest with context and guesswork. You can either pretend you get it, or you can get curious.

Curious is better.

Why Wandering Beats Pretending

The best learning did not come from sticking tightly to an agenda. It came from wandering.

I talked to vendors I was not shopping. I stopped at booths because of tchotchkes I did not need. I ran into Huddlers doing the same thing: Absorbing, comparing, trying to make sense of the landscape.

One random stop led to a company sitting on a goldmine of HR data that could be wildly useful to CMOs. I would not have found it if I had stayed perfectly efficient.

That is the lesson. In emerging spaces, over-optimization can make you less informed. You need some agenda. You also need room for discovery.

Why Sameness Is A Marketing Warning

Of course, wandering through a hundred AI booths also reveals another truth: Sameness is everywhere.

A lot of companies are saying the same thing. Faster. Smarter. Agentic. Automated. Copilot. Platform. Transformation. If you dropped the booth copy into a blender, most categories would come out as purple-gray soup.

Then one line broke through: “Someone’s gotta babysit the bots.”

That worked because it was human, specific, and slightly funny. It named a real anxiety in plain language. It made the problem memorable.

When you see a hundred companies saying the same thing, that is not only a branding problem. It is a leadership problem. Someone has to decide what the company actually believes, who it serves, and what it wants to be known for.

What CMOs Should Do After The Event

The post-event temptation is to collect slides, share a few notes, and move on. Resist that.

Instead, ask three questions.

First, what did we learn that changes our view of the market? Second, what should we test in the next 30 days? Third, where is our own messaging guilty of sounding like everyone else?

AI learning is not a spectator sport. It is not enough to attend the conference, collect the badge, and return with five buzzwords and a tote bag.

The CMO’s job is to translate curiosity into action.

If the room made you feel a little behind, good. That may be the most honest place to start.

Q&A

What should CMOs do when they feel behind on AI?

Admit it privately, then get curious publicly. Ask better questions, test small use cases, and learn with the team.

Are AI conferences worth attending?

Yes, if you use them for pattern recognition and discovery, not just vendor shopping.

What is the biggest marketing lesson from AI events?

Sameness is everywhere. Clear, human, specific messaging stands out faster than generic AI claims.

How should teams follow up after an event?

Turn notes into a short test plan: What changed, what to try, who owns it, and how you will measure learning.