Foundation Playbooks

Plan Family Vacations

As the EA, you manage end-to-end planning for family vacations. This includes researching and booking flights, accommodations, and activities, plus handling all related logistics. You will create a clear travel itinerary and monitor for changes or disruptions. All steps, decisions, and communications must be logged in GuideLayer > Task comments, with AI Copilot supporting research, comparisons, itinerary optimization, and troubleshooting. Why this matters: Vacations are meant to be stress-free for the executive and their family. By managing the entire process, you save the executive time, ensure preferences are honored, and deliver a seamless travel experience. This process also builds a record of family travel preferences, making future planning faster and easier.

Angel Ligeralde
Marketing Manager, HelpFlow
our PROCESS

Plan Family Vacation Playbook

Overview / Purpose

As the EA, you manage end-to-end planning for family vacations. This includes researching and booking flights, accommodations, and activities, plus handling all related logistics. You will create a clear travel itinerary and monitor for changes or disruptions.

All steps, decisions, and communications must be logged in AI Tool / Project Management Tool, with AI Copilot supporting research, comparisons, itinerary optimization, and troubleshooting.‍

Why this matters: Vacations are meant to be stress-free for the executive and their family. By managing the entire process, you save the executive time, ensure preferences are honored, and deliver a seamless travel experience. This process also builds a record of family travel preferences, making future planning faster and easier.

EXPECTED OUTCOMES

  • Flights, accommodations, and activities booked accurately and on time.
  • A comprehensive itinerary prepared and shared with travelers.
  • Potential disruptions (delays, cancellations) proactively monitored and resolved.
  • Family travel preferences documented in AI Tool / Project Management Tool for future trips.
  • All actions, updates, and confirmations fully logged in task comments.

When to Use / Scope

Use this playbook for any personal or family vacation where the executive requests planning support. It applies whether the trip is domestic or international and whether booked well in advance or at the last minute.

Pre-conditions

  • Trip purpose, destination, and travel dates confirmed.
  • Access to payment methods and traveler profiles (including loyalty numbers and preferences).
  • Executive approval to proceed with research and bookings.

Roles & Responsibilities

‍Executive Assistant – Gather vacation details, research and compare options, make bookings, prepare itineraries, monitor for changes, document all steps, and proactively flag issues.

Executive / Family Members – Review and approve final selections and share special requests or restrictions.

Finance / Operations (if applicable) – Approve and process payments, handle reimbursements, ensure policy compliance.

Templates & Tools

Tools: GuideLayer, AI Copilot, TripAdvisor, Expedia, Airbnb, Booking.com, Google Calendar.

AI Copilot Power Prompts:

  • “Summarize vacation request and flag missing details I should confirm.”
  • “Generate a side-by-side table of flight/hotel/activity options with pricing and reviews.”
  • “Compare these flight and hotel options and suggest top 3 based on budget and convenience.”
  • “Update client preference profile based on this vacation’s selections.”

Client Feedback Template:

Hi [Client], I’ve completed the bookings for your upcoming vacation and prepared your itinerary. Could you share a quick note—was everything aligned with what you envisioned? Any tweaks you’d like for next time?

Success Indicators / Metrics

  • 100% of bookings confirmed and documented in GuideLayer.
  • Itinerary shared ≥1 week before travel (unless last-minute).
  • Zero missed preferences (airline, seat, room type, dietary needs).
  • Proactive resolution of travel disruptions.
  • Reduced back-and-forth due to early clarification of preferences.

Best Practices, Tips & Pitfalls

Pro Moves

  • Ask clarifying questions early—avoid incomplete trip briefs.
  • Present 3–5 strong options with reviews, pricing, and convenience comparisons.
  • Deliver options in side-by-side tables for clarity.
  • Add all confirmed bookings and travel times to the executive’s calendar.
  • Use AI Copilot to update the family’s travel preference profile after each trip.
  • Monitor flight and accommodation statuses daily before and during travel.

Top Mistakes to Avoid

  • Starting research without full trip details.
  • Presenting too few or unverified options.
  • Skipping documentation in GuideLayer task comments.
  • Ignoring proactive monitoring of flights or reservations.
  • Failing to use AI Copilot for research and optimization.

Troubleshooting & Edge Cases

  • Unclear preferences: Use AI Copilot to summarize missing details and request clarification early.
  • Budget approval pending: Note in GuideLayer and flag for follow-up.
  • Overbooked hotels or flights: Maintain backup options and prioritize flexible bookings.
  • Family member changes plans: Adjust bookings and update itinerary immediately.
  • Last-minute trips: Use fast-booking platforms (e.g., Expedia, Google Flights) and focus on reliability over cost.
  • Lost confirmations: Store all confirmations in GuideLayer or shared folders.
01
Task Intake in AI Tool (GuideLayer)
  1. Receive the vacation request in AI Tool / Project Management Tool.
  2. Gather key details: destination, travelers, dates, budget, accommodation type, and activity interests.
  3. Confirm payment process (EA card, executive card, or direct client handling).
  4. Use AI Copilot prompt: “Summarize client vacation request and identify missing info I should confirm before research.”
  5. Ask clarifying questions on flights, accommodations, transportation, and food preferences.
02
Research & Option Compilation
  1. Research flight, accommodation, and activity options that fit preferences.
  2. Ensure all options are well-rated and aligned with the family’s comfort level.
  3. Present 3–5 curated options per category in a comparison table with reviews and pricing.
  4. Log all findings and notes in AI Tool / Project Management Tool.‍
  5. Use AI Copilot: “Compare these flight and hotel options and suggest top 3 based on budget and convenience.”
03
Executive Review & Selection
  1. Share the curated options with the executive for review and approval.
  2. Record all decisions, special notes, and updates in AI Tool / Project Management Tool.
  3. Use AI Copilot prompt: “Analyze selected options and update client preference profile for future vacations.”
04
Booking & Confirmation
  1. Confirm all bookings per payment protocol.
  2. Upload all confirmations (PDFs, screenshots) to AI Tool / Project Management Tool.
  3. Create a comprehensive itinerary including:
    • Flights (codes, times, baggage info)
    • Hotel details (address, check-in/out)
    • Transportation (car rentals, transfers)
    • Activities schedule (with reservation details)
    • Emergency contacts
  4. Add all items to the executive’s calendar with direct links to AI Tool / Project Management Tool.
  5. Deliver itinerary to travelers at least one week before departure.
05
Proactive Monitoring & Post-Trip Updates
  1. Track bookings and monitor for disruptions (delays, cancellations, closures).
  2. Use AI Copilot: “Generate backup itinerary options in case of flight delay or cancellation.”
  3. Communicate updates immediately and adjust itinerary as needed.
  4. After the trip, request client feedback and update travel preferences in AI Tool / Project Management Tool.

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