Before you hire a travel advisor: the questions that separate planners from order-takers

The five questions that tell you the most

Ask a travel advisor what kinds of trips they plan most, how they are paid, who they book through and what that gives you, what they will not do, and exactly what happens if something goes wrong while you are abroad. Ask for the fees in writing. Then notice whether they asked about you, your group and your reasons for traveling before they started talking about destinations, because that tells you more than any single answer.

I am on the other side of this conversation every week, and I welcome these questions. A client who asks them is a client who cares about the trip, and an advisor who is uncomfortable answering them is telling you something important. Here is how I would think about each one, and what a good answer sounds like.

• What kinds of trips do you plan most often?
• How are you paid, and what will I owe you?
• Who do you book through, and what does that unlock for me?
• What do you not do?
• What happens if something goes wrong during the trip?

What kind of traveler is your sweet spot?

Travel is too broad for anyone to be expert at all of it. An advisor who mainly books all-inclusive beach weeks will see different problems than one who plans a three-generation trip to Ireland or a business traveler's month of meetings. Ask what most of their trips look like, and ask for a recent example similar to yours.

My own focus is luxury travel, multigenerational family trips and corporate travel. My Fora profile also lists off-the-beaten-path travel, safari, Antarctica, Europe and Mexico, and my personal favorites include Switzerland, Tahiti, Italy and Argentina. If someone asked me to plan a budget backpacking trip, I would tell them I am not the right person, and that honesty is exactly what you want to hear when the trip is outside an advisor's strengths.

If you are hiring for business travel, the questions shift. Ask how quickly the advisor responds during the workday, whether they handle dining reservations and events as well as flights and hotels, and whether there is round-the-clock support when you are in a different time zone. My Unlimited Travel Planning retainer exists for exactly that kind of traveler, with 24/7 concierge service for travel needs, but not every advisor offers it, and you should know before you rely on it.

How do you handle a group whose needs pull in different directions?

If more than one household is traveling, ask this directly. A family trip with grandparents, parents, teenagers and toddlers is a different design problem from a couple's vacation, and the advisor should be able to explain how they balance pace, rooms, mobility and budget across the group. Listen for practical answers: building in time apart, choosing hotels where the family can be close without being on top of each other, limiting the number of moves, and having one or two decision-makers rather than a committee.

Multigenerational travel is the reason I founded RB Travel Collective, and a recent trip to Ireland to celebrate a retirement is a good example of what it involves: several households, different ages and interests, one itinerary that had to work for all of them. Many Dallas families I talk with have tried to plan this kind of trip through a group chat first. Ask the advisor what they would do differently, and you will learn quickly whether they have done it before.

How are you paid, and what will I owe you?

Advisors are paid in different ways: some charge planning fees, some charge nothing up front, some work on annual retainers, and many combine approaches. None of these is wrong. What matters is that you know before the work begins. Ask what the fee is, what it covers, what would change it, and whether it is refundable if you decide not to travel.

I publish my fees on my website, from $50 for a premium-cabin flight booking to $1,100 for a full two-week itinerary for a single family, and I note the situations that get a custom quote: last-minute travel, multi-group trips and trips of two weeks or more. I break all of that down in what a luxury travel advisor costs. Whatever advisor you choose, get the answer in writing.

Who do you book through, and what does that unlock?

Most independent advisors work under a host agency and may belong to one or more luxury networks. Those affiliations decide which hotels the advisor has relationships with and which amenities they can pass along. I book through Fora, and RB Travel Collective is a Virtuoso member. At partner hotels that can mean amenities such as a hotel credit, free breakfast and a possible upgrade.

The word to listen for is possible. A trustworthy advisor will tell you that upgrades depend on availability at check-in and will not promise one to win your business. Ask which properties in your destination are partners, what the amenities are at each, and how they compare with what you would get booking the same room yourself.

Then ask about the parts of the trip that are not hotels. Who arranges the guides, the drivers and the experiences, and how well does the advisor know them? On a full itinerary I book transfers, activities and excursions through trusted local partners, which is how clients end up with experiences that do not appear in any search result. An advisor who relies only on large tour aggregators can still plan a good trip, but you should know which kind you are hiring.

What happens when something breaks at six in the morning?

This is the question most people forget, and it is the one that matters most once you are in the air. Flights cancel, hotels oversell, a transfer driver does not appear, someone gets sick. Ask who you call, whether that person will actually answer while you are abroad, and what they did the last time a client's plans fell apart.

Full-service clients of mine have someone looking out for them during the trip, not just before it. One client whose trip hit several last-minute changes wrote that I handled everything seamlessly, so they could relax and enjoy the trip. A good advisor should be able to describe a real situation like that without hesitation. I go deeper on what you can do yourself, and what travel insurance does and does not cover, in what to do when plans change mid-trip.

Ask what they will not do

An advisor who says yes to everything is either very large or not being straight with you. Every good advisor has limits, and knowing them early prevents disappointment. Mine are simple: I book first, business and premium economy flights where it is a separate cabin, and I do not book economy fares. I am also not the right fit for a traveler who wants the highest level of service for little or no budget.

Ask, too, how they handle a request they think is a mistake. If you want five hotels in ten days with two grandparents and a toddler, will they tell you that is too much? The advisor who pushes back politely is protecting your trip.

Red flags that should end the conversation

Most advisors are honest and hardworking, and a single awkward answer is not a reason to walk away. A pattern is. If several of the signs below show up in the same conversation, keep looking, however good the destination ideas sound. The trip will only be as calm as the person managing it.

These are the patterns I would watch for, whoever is showing them:

• Fees that stay vague, or that appear only after you have committed.
• Promises of guaranteed upgrades or perks that no advisor can control.
• No questions about who is traveling, why, or what matters most to you.
• Cancellation and change terms they cannot explain in plain language.
• No clear answer about who supports you during the trip.
• Pressure to decide immediately, before you have seen a written proposal.

What a good first conversation feels like

The best first meetings feel more like an interview about your family or your work than a sales pitch. A good advisor wants to know who is coming, their ages and mobility, the occasion, the pace you enjoy, the trips you loved and the ones you did not, and what you would happily give up to protect what matters most. Destinations come later.

After that conversation, a good advisor should come back with a proposal you can actually evaluate: where you will stay and why, how the days are paced, what is private and what is shared, and what the trip will cost in total. It should feel like it was written for your group, not pulled from a brochure. If the proposal could have been sent to anyone, the listening did not happen.

I meet many clients in person in Dallas, and others by phone. I listen first, then tell you honestly whether the trip you are imagining fits the group, the season and the budget. If you are not sure whether you need an advisor at all, my guide on whether a trip is too complicated to plan yourself may help you decide, and for large family trips my guide to planning a trip for three generations shows the kind of questions I ask.

Bring these to the first meeting

You will get far more from any advisor if you arrive with a few facts in hand. You do not need a finished plan, just enough to make the conversation concrete:

• Your rough dates and how flexible they are.
• Everyone who is traveling, with ages and any mobility, health or dietary needs.
• A budget range for the trip, excluding flights, and who is paying for what.
• Two or three trips you loved and one you did not, and why.
• The non-negotiables: a celebration date, adjoining rooms, a quiet hotel, a direct flight.
• Passport expiration dates for everyone in the group.

Questions people ask me