How to Book Stress-Free Travel for Executives in 7 Steps

No question: Booking travel for executives requires careful management of competing priorities. You’ll likely have to deal with last-minute schedule changes, executives’ specific preferences, premium service expectations, and the pressure of knowing a missed connection could derail a critical meeting.

And when you support multiple executives — each with their own airline loyalties, hotel preferences, and dietary requirements — the coordination compounds.

This guide breaks down how to book travel for executives step by step, from initial trip requirements through post-travel reconciliation, and how to reduce your workload with a travel management platform.

How to Book Travel for Executives

Executive travel booking follows a predictable sequence. Here’s how to execute each phase.

1. Clarify Trip Purpose and Constraints

Before you even look into bookings, confirm the executive’s trip goal(s), key meetings, locations, and required arrival and departure windows. For example, flying to a 9 a.m. board meeting means your executive should probably land the night before.

Check your company’s travel policy, approval requirements, and budget limits before searching options. If the destination carries elevated risk (someplace with, say, political instability, health advisories, or security concerns), flag those issues early so you can arrange appropriate insurance, security briefings, or alternative accommodations.

2. Gather Profile Information and Documents

Here’s a tip that will make your job easier: Build and maintain a complete traveler profile for each executive you support, including their:

• Legal name (exactly as it appears on their ID)
• Date of birth
• Loyalty program numbers
• Known Traveler Number (KTN) or redress number
• Seat preferences
• Hotel brand and amenity preferences
• Dietary requirements
• Accessibility needs

Fortunately, travel management platforms can store this information so that executive assistants can book trips more efficiently.

But don’t leave anything to chance: Verify that passports, visas, and any required vaccinations remain valid for the entire trip, including buffer time if travel dates shift. For international travel, check entry requirements at least two weeks before departure.

3. Build the Itinerary Skeleton

Now it’s time to map out the executive’s plans. Plot meeting times on a timeline, then work backward (to determine when your executive needs to arrive) and forward (to determine when they can depart). Build flight windows, hotel nights, and ground transportation around those anchors with realistic buffers for delays, traffic, and any time-zone adjustment(s).

For complex multi-city trips, prepare one or two alternate itineraries with different options for travel time, comfort, and cost. Presenting options lets your executive make a quick decision rather than needing to review every possible flight. Clearly frame the options and tradeoffs. For example: “Option A arrives two hours earlier but requires a connection; Option B is nonstop but lands at 4 p.m. instead of 2 p.m.”

4. Book Flights, Hotels, and Ground Transportation

Then dive into the booking process. Remember, you’re booking for executives, so select flights that minimize stress as well as cost. Prioritize reasonable departure times, limited connections, and an appropriate cabin class — especially when a tight schedule or high‑stakes meetings are involved — even if that sometimes means choosing a flight that isn’t the lowest-priced option.

When it comes to picking a cabin class, match options to trip length and company policy; many organizations allow business class for international flights over a certain duration while requiring economy for domestic flights.

Then, choose hotels near meeting locations — ones with the amenities your executive requests and/or uses, such as:

• Reliable Wi-Fi
• Workspace
• Late check-in
• Compatibility with their preferred loyalty program

Don’t forget about airport transfers and ground transportation. Arrange specific pickup instructions, driver contact information, and backup options if the primary arrangement falls through. For high-stakes arrivals like investor meetings or board presentations, consider services with live flight tracking that adjust pickup times automatically when flights are delayed.

5. Route Approvals and Confirm Payment

Before ticketing, route the completed itinerary through your company’s approval workflow.

Some organizations require a manager or finance team member’s sign-off for trips exceeding certain thresholds, while others need travel manager approval for international bookings or premium cabin classes.

Attach the correct project codes, cost centers, and payment methods during booking.

6. Prepare the Travel Itinerary

Now it’s time to show off your organizational skills. Create a single, mobile-friendly itinerary document containing everything your executive needs:

• Flight details with confirmation numbers
• Hotel addresses with check-in times
• Ground transportation pickup locations with driver contacts
• Meeting times with addresses
• Time zone references for each location

Include emergency contacts, your phone number for urgent issues, and any tickets or QR codes your executive will need. Send calendar invites that block travel time and include location details to help your executive avoid accidentally scheduling a conflict when they're travelling.

7. Confirm Before Departure and Support During Travel

Mark your calendar: A day or two before departure, check for any flight schedule changes, verify hotel reservations, and confirm car service pickup times. Handle online check-in and boarding pass downloads so your executive doesn’t have to deal with stopping at an airport kiosk.

While the executive is traveling, monitor for disruptions. When you spot a delay or cancellation before your executive does, you can present possible solutions. For example: “Your 2 p.m. flight is delayed three hours; I’ve already identified a 1 p.m. option on another carrier. Would you like me to switch you?”

When the trip is over, promptly reconcile the executive’s expenses, collect any feedback about what worked or didn’t, and update saved preferences based on what you learned.

What to Look for in an Executive Travel Management Platform

Managing one trip for an executive can be a lot, and EAs already have plenty on their plates. Executive travel solutions can offer game-changing efficiencies. The best platforms combine booking, payments, expense management, and traveler support in one place, offering six specific capabilities designed to reduce manual coordination:

1. Centralized Preference Management

When you support multiple executives, it’s hard to keep up with their preferred airlines, seat selections, and hotel brands. Your travel management platform should apply these preferences automatically during booking.

That’s exactly what Navan does: The platform stores these profiles and applies them instantly, so booking becomes a matter of confirming details rather than re-entering them.

2. True Delegate Booking Capabilities

Instead of sharing travel itineraries over email or text, your travel management platform should allow you to suggest options for what an executive can approve themselves in the app, and when you should be looped in.

For example, with flight delays, gate changes, and cancellations, the traveler should receive direct notifications, while you only receive copies of booking confirmations. Executives stay informed without overwhelming you with every minor update.

3. Itinerary Coordination and Calendar Integration

Calendar integration eliminates manual itinerary updates. Navan automatically adds flights, hotels, and travel details to your executive's calendar — and when bookings change, updated itineraries go out via email and calendar invites without you lifting a finger.

In-app and printable itineraries keep everyone aligned. Executives can pull up trip details in the app or rely on a clean, printable itinerary for their briefcase or car. You can easily export or forward itineraries to security teams, office operations, drivers, or family members who need arrival details. Everyone knows where the executive is and when they’ll arrive, reducing back-and-forth coordination and last-minute confusion.

4. Group and Event Travel Management

Leadership offsites, board retreats, and client events can require coordinating travel for dozens of attendees — a process that becomes unmanageable when handled booking by booking. The solution is to set event parameters once and let attendees self-serve within your guardrails.

Navan Group Travel lets you define arrival and departure windows, allowed booking types, and spending limits. Attendees book themselves while you maintain visibility into actual versus estimated costs as bookings happen. For recurring routes, you can reuse previous itineraries to save setup time on repeat trips.

5. VIP-Grade Services and Proactive Support

Executive travel often demands premium services that standard programs don’t include: black car service, lounge access, expedited security, and dedicated support. Navan integrates many of these needs directly into the booking flow, so you can arrange cars, seats, and other preferences alongside flights and hotels. Through Navan’s supplier relationships, executives can benefit from negotiated rates and perks, such as flexible cancellation policies or preferred rooms, that aren’t typically available when booking on public sites.

For travelers who require a higher level of support due to their roles or trip complexity, Navan Pro — powered by Reed & Mackay — provides white-glove service.

6. Proactive Disruption Management

Real-time flight monitoring helps identify potential delays, cancellations, and connection risks before travelers even get to the airport. Predictive models analyze weather patterns, connection risks, and delays to identify emerging disruptions hours before departure, send alerts, and proactively rebook flights.

7. Built-in Flexibility for Business Schedule Changes

Travel disruptions aren't the only reason itineraries change. Meetings get cancelled, deals run long, and clients ask for dinner the night before departure. A platform that charges change fees or requires phone calls for every modification slows you down when schedules shift for business reasons.

Look for self-service rebooking that lets you extend hotel stays, swap same-day flights, or adjust ground transportation directly in the app. Navan lets both EAs and executives make these changes instantly — no hold times, no back-and-forth with support. When a board meeting gets extended by a day, adjusting the return flight takes minutes.

8. Access Controls for Sensitive Itineraries

For executives whose travel details shouldn't be widely visible, whether due to competitive sensitivity, personal safety, or simply discretion, the platform should let you control who sees what. Standard company-wide travel dashboards can inadvertently broadcast executive movements to employees who don't need that information.

Navan allows admins to configure role-based visibility, restricting itinerary access to specific individuals rather than entire teams. You decide who receives booking confirmations and views trip details in reporting dashboards. Sensitive travel stays visible only to those with a legitimate need to know.

Book Executive Travel with Navan

By following the same booking sequence for every trip, you don’t have to start from scratch each time. You know what to ask, when to escalate, and where things typically go wrong.

The right platform makes that process faster. Navan’s all-in-one platform combines delegate booking, automated expenses, and 24/7 support in one interface.

Get started with Navan today.