There is a short note at the end of this issue that may be relevant if you've been thinking about starting a newsletter or being more consistent with one.

Four years of writing The Expert’s Guild Weekly gave me a front-row seat to something I did not expect to watch this closely.

I have seen this newsletter evolve.

I have seen this industry shift.

And I have watched both move through the AI moment in real time, from the outside curiosity to the daily adoption to what is actually happening now inside real advisory businesses.

That gives me something worth sharing. Not theory. Observation.

It starts with a newsletter that used to take me three days to write.

When I launched The Expert’s Guild Weekly, it was just me, a blank page, and everything I wanted to say to this industry.

Three days to write every issue. Research, writing, editing, formatting.

Early tools helped.
Grammarly cleaned the prose.
Hemingway tightened the sentences.
Jarvis, which became Jasper, started cutting the time in half.
Three days became one.
I was more productive and I was happy.

Then AI arrived.

ChatGPT, Claude, and Gemini, and something different happened.

These were not editing tools. They changed the workflow itself. And watching that shift in my own work made me pay close attention to how the advisors around me were using the same tools.

What I saw was not what I expected.

I have a talented team of travel advisors.

World connoisseurs in the truest sense.

They know destinations, suppliers, properties, and experiences at a level that takes years to develop.

And yet when they open ChatGPT, that knowledge largely stays outside the conversation.

They type a question the same way they used to type into Google.

They ask for an itinerary and keep the first version that comes back.

They start from scratch every single time, as if the previous conversation never happened.

The output sounds like AI wrote it. Because AI did write it, without their voice, without their standards, without any of the judgment that makes them worth calling in the first place.

The problem is not the tool. The problem is the way they are using it.

There is a name for what they are doing.

They are querying AI.

And querying is not the same thing as thinking with it.

Querying AI is asking for an answer.

Thinking with AI is something else entirely.

It is bringing context, judgment, constraints, client nuance, voice, and accumulated experience into the conversation before asking it to produce anything.

The difference sounds small. The output is completely different.

An advisor who knows Portugal does not ask AI for a romantic five-day itinerary. She knows the couple should not split every night between Lisbon, Porto, and the Douro just because the map makes it look easy. She knows they want food without performance, a hotel with real neighborhood texture, and one private experience that feels personal instead of packaged.

That context is the value. AI can help shape it, express it, and personalize it, but only after the advisor brings the judgment into the room.

AI cannot know which beautiful itinerary is wrong for the client. The advisor knows.

The question is whether that knowledge enters the tool before the output is generated.

Most of the time, it does not.

They have the expertise. They are leaving too much of it outside the prompt.

AI used well does not flatten the advisor's expertise. It makes the expertise easier to organize, express, personalize, and repeat without draining the advisor every time.

That is the real shift. Not using AI more. Using it with more of yourself inside it.

The advisors getting real value from these tools are not the ones asking better questions. They are the ones bringing better context.

Before I go further, I want to be transparent about something.

I’m considering adding a dedicated section to this newsletter focused entirely on AI for travel professionals.

Practical workflows, real use cases, and prompts that actually work, built around how this profession operates rather than how the tech world thinks it does.

But I am not going to build it around what I think you need. I want to know where you actually are right now, because I want to give you something valuable every week.

Not where you think you should be. Where you actually are.

There is no wrong answer.

I’m asking because what I write next depends on understanding where this community actually stands. Take five seconds. Answer honestly.

I will be watching the responses closely.

Hit reply if you want to add anything. I read every response.

Until next week.

Alex

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