Good AI output starts with good context. Before asking AI to plan anything, gather the information you would normally need yourself: destination and dates, purpose of the trip, key meetings, preferred airports and airlines, hotel preferences, loyalty programs, seat preferences, budget, ground transportation needs, schedule flexibility, and any required approvals.

Once you have that information, AI can help turn a broad request into a manageable set of options. Instead of jumping between tabs while trying to remember whether Flight A arrives early enough for the first meeting or Hotel B is actually close to the client’s office, ask AI to organize your options around the priorities that matter most to your executive.

For example, you might ask it to compare three possible flight and hotel combinations based on total travel time, number of connections, arrival time, location, executive comfort, and schedule fit. Use AI to quickly compare the options, surface the tradeoffs, and organize the details. You still apply your judgment and make the final decision.

Then comes the important part: verify. Actual fares, availability, cancellation policies, baggage rules, hotel details, and other booking information should still be confirmed through your company’s travel platform or directly with the provider.

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Once the trip is booked, AI becomes less of a researcher and more of an organizer.

Take the confirmed flight, hotel, ground transportation, meetings, addresses, restaurant reservations, time zones, and other trip details and ask AI to organize them into a single itinerary. Instead of manually reformatting information from five different confirmation emails, you can use AI to create the first structured draft and then review it for accuracy. If you already have an itinerary format your executive prefers, attach a sample and ask AI to use it as the model for the new itinerary. This helps keep the structure and level of detail consistent from trip to trip.

But don’t stop at formatting. This is also a great moment to ask AI to be your second set of eyes. Give it the itinerary alongside the executive’s schedule (a screenshot of the relevant calendar dates works, too) and ask it to look for time-zone mistakes, overlapping commitments, unrealistic airport transfers, insufficient travel buffers, early departures after late events, or meetings that technically fit on the calendar but don’t make sense in the real world.

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Your working itinerary might contain every confirmation number, address, phone number, reservation detail, and backup plan. Your executive probably doesn’t need all of that.

Once you’ve built and checked the master itinerary, ask AI to create a concise executive travel brief answering the questions that actually matter (if your executive has a preferred format, attach a sample and ask AI to follow its structure and level of detail): Where am I going? When do I need to be there? Who am I meeting? Why does it matter? How am I getting there? What do I need to remember? Include the hotel, transportation, weather, key meeting context, and a few important reminders, but leave the operational clutter in your master version.

Then, 24-48 hours before departure, return to the trip for a final quality check. Confirm flight status, seats and boarding passes, hotel and ground transportation, meeting locations, travel times, time zones, weather, restaurant reservations, travel documents, and known disruptions.

AI can help you create the checklist and compare your latest information against the itinerary, but real-time information should always be verified with the airline, hotel, transportation provider, travel management company, or appropriate official source.

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Of course, even the best itinerary rarely survives every flight delay, meeting change, or last-minute request.

When something changes, AI can help you quickly understand the ripple effect. Give it the confirmed change and the current itinerary and ask which meetings, transportation arrangements, reservations, or calendar blocks may now be affected. It can also help you reorganize the schedule and draft quick updates to the people who need to know. You remain the decision-maker. AI can surface alternatives and help communicate the change, but actual cancellations, rebookings, fees, availability, and other consequential decisions should be confirmed through the appropriate provider.

And don’t forget the trip after your executive gets home. AI can help organize receipts and expense information, identify follow-ups, draft thank-you notes, summarize relationship notes for your CRM, and capture preferences that will make the next trip easier.

Those small observations eventually become something even more valuable than an itinerary: an Executive Travel Profile that helps you anticipate what your executive needs before they have to ask.

Microsoft’s latest Copilot release notes confirm that it can now reason across an entire inbox, calendar, and meetings, including delegate calendars, so EAs can ask natural‑language questions like “Summarize next week’s travel and related meetings” or “Find all emails about the Berlin trip and highlight action items,” with data access controlled by existing M365 permissions.

Google’s new Gemini 3.7 Flash model is generally available and billed as its “most intelligent workhorse” for coding and agents, with substantial improvements on business‑workflow benchmarks and availability across the Gemini app, Gemini Spark (AI Pro/Ultra), Gemini Enterprise, and the Gemini API - giving EAs more reliable agent‑style behavior when they use Gemini to orchestrate multi‑step tasks like email + calendar + travel briefs.

Slack’s August 2026 admin update adds agents to direct messages, expands Slackbot into slides, reports, and dashboards based on workspace data, and introduces adjustable AI content‑safety filters (Default, Maximum, None) via a new Guardrails section, so organizations can both empower EAs with in‑Slack AI assistance and tighten controls for regulated environments or EU AI Act compliance.

AI can be a powerful researcher, organizer, and second set of eyes, but you remain the final authority. Always independently verify bookings, changes, fares, flight status, travel requirements, and anything involving significant cost, safety, or legal considerations.

Keep privacy in mind, too. Executive travel can reveal schedules, locations, confidential meetings, payment information, and personal preferences. Avoid sharing sensitive information such as passport details, credit card numbers, credentials, or confidential meeting information with public AI tools. Stick with your organization’s approved systems.

You also don’t need to overhaul your entire travel process to get started. Pick one upcoming confirmed trip, give the itinerary and schedule to your approved AI tool, and ask it to identify potential scheduling or logistics issues and create a one-page executive brief. Give yourself 15 minutes. If AI catches one missing buffer, surfaces one conflict, or saves you from manually formatting the brief, you’ve found a practical place to start.

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The Base Team