Questions to ask before someone books travel on your behalf

Most people who hand their travel booking to someone else make the same mistake: they assume capability from a polished pitch or good references, then only discover gaps when the itinerary is half-built or a flight is already booked wrong. The fix isn't a longer interview—it's asking the right questions and listening to how the answers come back. What matters is not just what they say, but whether they ask you clarifying questions in return, and how they handle the messy details that aren't on your first list.

Questions that reveal how they actually work

Start by asking them to walk you through their process for a trip like yours. Not a template answer—ask them to describe it step by step. Do they immediately ask about your preferences (aisle or window, hotel proximity to meetings, dietary needs), or do they assume? A good coordinator will interrupt themselves to ask. They'll want to know if you'd rather a 06:00 flight to save a hotel night or if you'd lose productivity on arrival. They'll ask whether you need a car or public transport, whether you're working from the hotel or only sleeping there.

Next, ask how they handle changes. Business travel changes. A meeting gets rescheduled, a client asks you to add a day, or a flight gets cancelled. Do they make changes themselves and notify you, or do they loop you in for approval each time? What's their communication channel—email, WhatsApp, a shared document? A strong answer includes a concrete example: "Last week my client's flight was cancelled. I checked alternative routes within two hours, booked a comparable flight on the same airline for the same price, and sent her a WhatsApp summary with the new confirmation before she even knew there was a problem." An evasive answer sounds like: "Oh, we handle all that." You want specifics.

Ask them directly: what happens if they book something wrong? If they reserve a hotel in the wrong area or miss a connection window, how do they fix it and what does that cost you? Their answer should include accountability. A coordinator worth their rate will say something like: "I eat the cost if it's my error. I'd immediately contact the hotel or airline to rebook, keep you informed of the new arrangements, and absorb any rebooking fees." If they hedge or suggest you'll need to sort it out, that's a flag.

Find out how they manage your preferences over time. Do they take notes on what worked and what didn't—your preferred airline, hotel chains, whether you like city-centre locations or quieter spots? Will they remember next trip that you had a bad experience with a particular hotel or transit route? This matters because good coordination improves with repetition.

The questions about money and boundaries

Ask whether they'll book only with your pre-approval, or if they'll use their judgment on lesser decisions. Some people prefer a coordinator who makes choices on amenities (upgrade seat, nicer room within budget) and only checks in on major calls. Others want approval on everything above a certain cost. Be explicit about this—and ask how they'd communicate prices as they go. Do they send you links and costs as options, or do they present a finished itinerary? There's no wrong answer, but you need to be aligned.

Ask for an example of when they've pushed back on a client's request. Have they ever told a client their preferred hotel was poor value, or that a routing was inefficient? A coordinator with confidence and judgment will have a story. If they've never disagreed with a client, they're either extraordinarily lucky or they're not thinking critically.

Finally, ask how they'd explain all the bookings to you. Would they send you a single master document, separate confirmations, or a weekly summary? What format works for you when you need to share details with an assistant or expense team?

Listen not just to the answers, but to whether they ask you questions back. A coordinator who listens harder than they talk is usually the one who'll get details right.

When you're ready to brief someone, Strove hosts verified travel coordinators who invite exactly this kind of scrutiny. Find one, ask these questions, and move forward with confidence.