Executive Assistant Travel Planning: How EAs Book and Run a Trip

The Work Behind a Business Trip

Executive assistant travel planning turns a line on a calendar into a trip the executive never has to think about. The flights land with margin to spare, the hotel is close enough to walk to the meeting, and a car is waiting wherever there’s no train. It’s one of the most skilled things an assistant does, and almost none of it is visible in the finished itinerary.

I’m Nir Sabato, co-founder of Catch. This page is for whoever currently does this job: the EA, the chief of staff, or the founder booking their own flights at eleven at night. The first half is the craft, laid out roughly the way an experienced assistant works through it. The second half is what’s changed, which is that Catch now books business travel end to end and keeps managing the trip after it’s booked.

If you already do this well, none of the first half will surprise you. It’s here because the people who buy travel tools rarely see how much judgment the job actually takes.

The Craft: How a Good EA Plans a Trip

Planning a trip well is a sequence of decisions, and the order matters more than people expect. Fares come last.

Read the calendar before you look at a single fare

Start with what the trip has to achieve. Open the calendar and the relevant email threads and work out its real shape: which meetings are fixed, which are still being negotiated, which one is the reason for going at all, and where each one physically happens.

A trip built around a 9am board meeting on Wednesday is a completely different trip from one built around a conference where the only fixed commitment is a Thursday afternoon panel. The first has almost no tolerance in it. The second has a whole day of slack.

You also read what isn’t on the calendar. If your executive has three people in that city they haven’t seen in a year, the trip is probably worth an extra evening. A booking site has no way of knowing that. You do.

Time the flights against the meeting windows

Flight selection is a meeting problem before it’s a price problem. The question isn’t the cheapest way to get there. It’s which departure protects the first commitment, and which return doesn’t strand them.

The rules experienced assistants apply are pretty unglamorous. Don’t land the morning of a meeting that matters, unless the schedule gives you no choice. Build a buffer for the ground leg, since the airport is rarely the hard part. Watch the last connection of the evening, because a delay against it turns a missed flight into a missed morning. And check what the return does to the next day. A red eye that saves four hundred dollars can cost a Thursday that was already fully booked.

Then apply the preferences. Aisle. The carrier they hold status with. Nothing before 7am if they’re useless before 7am.

Choose the hotel by proximity, not by rate

The highest-leverage decision in the whole trip is probably the hotel, and it’s chosen by walking distance to the actual meeting address. Not by the city. Not by the nightly rate.

Ten minutes on foot from the office they’re visiting is worth a lot more than fifty dollars a night. It removes a car, a variable, and the odds of arriving flustered. Get it wrong and you’ve quietly added two taxi rides a day and a hard dependency on traffic for the entire trip.

After proximity come the things they’ve complained about before. A gym that opens early. A desk they can actually work at. A room away from the elevator. That list isn’t preference trivia; it’s the difference between an executive who arrives functional and one who doesn’t.

Fill the gaps with ground transport

Between the airport and the hotel, the hotel and the meeting, the last meeting and the return flight, there are gaps. Each one is a car, a train, or a walk, and each one gets decided before the trip rather than during it.

The gaps also tell you whether the schedule is real. If a 2pm across town follows an 11am that’s already tight, someone has to move something, and it’s far easier to move it now than from the back of a car.

Keep a preferences file, and keep it current

Assistants who are fast at this are fast because they aren’t re-deciding anything. Somewhere there’s a document with the passport details, the loyalty numbers, the seat preference, the airline they refuse to fly, the hotel chains they like, dietary requirements, and the note about wanting late checkout every single time.

Every trip adds to it. The hotel that turned out to be too far. The 6am departure that was a mistake. The car service that was reliable. That file is the real asset in this job, and it’s why a good EA books a trip in fifteen minutes that would take someone else two hours.

Re-plan when the flight moves

Most of the effort in travel planning goes into holding the plan together after it’s made, not into making it.

A meeting moves and the return flight is suddenly wrong. The airline cancels and every rebooking option is bad in its own way. The client pushes from Tuesday to Wednesday, so the hotel, the flight, and the car all have to change together. This is the part that eats the day, because it shows up without warning and it won’t wait.

It’s also the part that sits outside what a booking tool does. The tool shows what’s available. Someone still has to weigh the options against everything else in the week and pick one.

How Catch Handles Travel Planning End to End

Catch does this work end to end, from the same calendar and email context you’d have read yourself. It isn’t a booking platform you search. There’s no travel screen to open. You ask in whatever channel you already use, or Catch raises the trip before you get around to it.

It spots the trip before anyone asks

A conference ticket lands in the inbox. A meeting appears on the calendar in another city. A flight gets booked with no hotel against it. Catch reads those triggers and comes back with the flight and the hotel already worked out, ready to book.

That’s where most of the savings actually come from. Trips get booked when they surface, not two weeks later once the fares have moved.

It books flights, hotels, and ground transport itself

Catch operates as the travel agent. It books the flights, the hotel, and the ground transport directly rather than handing you a search page with filters. Where the company has a travel policy, Catch books within it: the rates, the approval flows, the upgrades that are authorized.

It applies what it has learned about the traveler

The preferences file stops being a file you maintain. Airline, seat, flight times, hotel class, room type, whatever requirements someone has flagged before, Catch carries all of it forward. Complain once about a hotel with no gym and Catch weighs that into every stay it offers afterwards.

It handles the last mile, including by phone

This is the part booking tools leave to the traveler. Catch picks the hotel by proximity to the actual meeting address. It calls the front desk to confirm a room detail, arranges the late checkout, books the restaurant, orders the car. Those are real outbound phone calls placed on your behalf, and voice is included in the plan with no per-call fees.

It keeps managing the trip after booking

The work continues after the booking is made. Catch watches for a better rate, and where the booking is on a flexible rate it cancels and rebooks. When the trip moves, it rearranges the pieces that depend on each other. When something changes on the day, it deals with it and tells you what it did.

Who This Is For

• Executive assistants and chiefs of staff who plan frequent trips and want the booking and re-booking off their desk
• Founders and executives who currently do their own travel planning between other work
• Executives at growing companies and owner-operator businesses who travel repeatedly to the same cities, conferences, and clients
• Teams without a dedicated EA where travel planning gets absorbed by whoever has time
• Executives with an assistant who’d rather that person spent their hours on the work only a person in the building can do

How It Works

1. Connect your email and calendar - setup is self-serve and takes under three minutes. No workflow builder, no configuration.
2. Catch reads the context - the calendar, the threads, the confirmations already sitting in your inbox.
3. Ask, or wait to be offered - say “I need to be in Chicago Tuesday to Thursday” in Slack, email, text, or on a call. Or let Catch raise the trip when it spots the trigger.
4. Review and confirm - early on, Catch checks with you before it acts. As it learns how you travel, it handles more on its own.
5. Catch runs the trip - bookings made, last-mile details arranged, rates watched, changes handled until you’re home.

What Changes

The planning time goes away. The tab-juggling a trip takes, plus the second round of it when something moves, stops being anyone’s work.

Trips get booked earlier. Booking becomes a two-line exchange, so it happens when the trip appears rather than when someone finally finds an hour. That’s where the meaningful savings sit.

Nothing depends on one person’s availability. Catch works around the clock and answers in seconds. A flight cancelled at 11pm doesn’t wait for the morning.

The cost sits differently. A fully loaded US executive assistant runs somewhere around $120,000 to $180,000 a year. Catch is a flat $99 a month, voice included, no per-call fees. None of which is an argument for letting anyone go. The traditional admin work is handled; the person doing it today grows into the operational and in-person work Catch doesn’t cover.

Frequently Asked Questions

Get Started

If you plan trips for someone else, or you plan your own between everything else, the fastest way to see the difference is to hand Catch the next one. Connect your email and calendar, tell it where you need to be, and see what comes back.

Get Started with Catch for $99 a month.