The question I wish every client would ask me has nothing to do with where I’ve traveled.
Clients ask good questions.
“Have you been on this ship?” Yes, or I know someone who has, and I can tell you what they found in cabin category D versus E and why it matters.
“How do you charge?” A planning fee, and here’s exactly what it covers.
“What happens if something goes wrong?” You call me directly — not a hold queue.
Those are the right questions. They tell you whether I can actually do what I’m promising.
But the question that changes the outcome of a trip more than any of those — the one almost nobody asks — is this:
What’s the best process for collaborating with you once I see the first draft?
Here’s what I tell the clients who do ask.
I want honest feedback. Not polite feedback, not “this looks great, let’s go with it” feedback when something in the back of your mind isn’t sitting right. Honest, specific, timely feedback — the kind that requires you to actually think about what I’ve put in front of you.
If the pacing feels rushed, say so. If the hotel I suggested doesn’t match what you had in mind, tell me what you were picturing instead. If you went looking at alternatives on your own — Tripadvisor, a travel blog, an AI tool — and something caught your eye, bring it to me. I’m not threatened by outside research. I’m in a better position to evaluate it than you are, and more often than not, there’s a specific reason I didn’t suggest it. Sometimes there isn’t.
What I can’t work with is silence.
The clients who come back after a trip and tell me it was exactly right — not “amazing, thank you” in the polite way people talk to their service providers, but actually exactly right — are almost always the ones who pushed back somewhere in the planning process. They flagged the restaurant they weren’t sure about. They said the second week felt over-scheduled and they wanted more room to breathe. They sent me something they found on their own because they felt a little nervous raising it.
Those conversations made the trip more theirs.
The clients who defer entirely — who trust me so completely that they never question anything I suggest — often end up with a trip that’s 90% right. Which is a good trip. But it isn’t the one I could have built with their participation.
I work best as a collaborator. The itinerary I’m most proud of building came out of five rounds of feedback, one genuine disagreement about a departure city, and a last-minute hotel change the client felt almost too awkward to bring up.
It was the right trip.
If you’re thinking about working with a travel advisor — me or anyone — ask that question. Ask how they want to hear from you when something doesn’t feel right, when you find something on your own, when you’ve changed your mind about something you said you wanted.
A good advisor will have a real answer.
If you’re in the early stages of planning something and want to think out loud about it, my DMs are open. No commitment. Just a conversation.
