Would You Trust AI to Run Your Executive’s Schedule? A Question Every EA Must Now Answer
- Richard Arnott
- Nov 26
- 3 min read
Executive Assistants have always been the quiet architects of order in an executive’s world. Travel plans, last-minute diary changes, stakeholder meetings, conflicting priorities—somehow, it all gets resolved. Increasingly, however, AI is being positioned as the new solution to the chaos, with promises of effortless itinerary planning, automated meeting coordination, and even real-time travel adjustments.
But here’s the real question: would you trust AI—right now—to handle every detail of your executive’s schedule? And more importantly: should you?
Sundar Pichai, Google’s CEO, recently warned that while AI is astonishingly capable, it is also prone to subtle errors and should not be “blindly trusted.” For Executive Assistants, that warning hits close to home. When one small slip in a travel plan can cascade into a missed meeting, a lost deal, or an embarrassed executive, “trust but verify” is more than a philosophy—it is professional survival.
Where AI Can Genuinely Help
Let’s be fair: there is a lot AI gets right. Many EAs already rely on it to:
generate draft itineraries
prepare first-pass travel options
identify time zones, flight times, and meeting windows
offer alternative schedules or suggest more efficient sequences
capture key travel rules and preferences when clearly input
In fact, for repetitive admin such as gathering flight options, organising accommodation lists, or mapping locations, AI is exceptionally useful. It is fast, consistent, and tireless—a brilliant assistant to the assistant.
Many EAs are finding that AI can easily handle 70% of the groundwork, leaving them to apply judgement, experience, and nuance to the remaining 30%.
But Would You Let AI Run the Entire Show?
Here’s where things become less comfortable.
Planning an executive’s movements is not simply a matter of stitching together flights and meetings. It requires:
awareness of the executive’s energy levels
understanding unspoken political sensitivities
reading between the lines of an invitation
knowing when “optional” actually means “attendance essential”
accounting for personal preferences that are never written down
anticipating risks, delays, and cultural contexts
knowing which people must be prioritised—and which can safely be declined
AI does not yet understand the texture of an executive’s world. It lacks the organisational history, the intuition, and—crucially—the subtle signals that EAs absorb over many years.
Ask AI to plan a schedule, and it will likely produce something neat, logical, and impressively structured.
But will it notice that back-to-back meetings with two feuding stakeholders will cause chaos? Will it avoid booking a flight that always runs late? Will it know your executive likes 15 minutes of silence before a big investor pitch? Will it sense that a “casual coffee” in Singapore is actually a politically significant meeting?
Not yet!
This is exactly why Pichai’s warning matters: AI sounds confident even when it is confidently wrong—and that can be a dangerous combination in the world of executive support.
So Should EAs Trust AI Today?
Here is the honest answer: trust it to support you, but not to replace you.
AI is brilliant at the heavy lifting: gathering information, suggesting routes, checking calendars, comparing options, remembering preferences—when those preferences have been clearly stated.
But travel planning, meeting orchestration, and high-level scheduling are not administrative tasks. They are acts of judgement. They require context, diplomacy, and emotional intelligence—things no AI can offer.
In many ways, AI has shifted the EA role upwards: less time spent piecing together flight data, more time spent thinking strategically about the executive’s goals, relationships, and priorities.
But the idea of handing over the entire process to AI? At this stage, that would be handing over something far too valuable.
A Better Way Forward
Rather than asking whether AI can be trusted, a better question might be:
How can you use AI to become even better at controlling the schedule rather than surrendering it?
EAs who excel in the AI era will be those who:
let AI gather 80% of the inputs
use their expertise to refine the final 20%
apply judgement to nuance, politics, personality, and risk
“quality check” AI outputs with the sharp eye only a seasoned EA has
This is the partnership model that works today—and the one that protects your executive, your role, and your professional reputation.
In the End…
Would you trust AI to fully plan your executive’s travel, meetings, and itineraries right now?
Probably not—and rightly so.
But would you trust AI to help you plan them faster, smarter, and more accurately than ever before?
Absolutely.
AI is the assistant to the assistant, not the replacement. The EA who understands that will remain indispensable, no matter how intelligent the technology becomes.
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About the Author: Richard Arnott, BA, FInstAM, FIToL, is a Director of BMTG (UK) Ltd, and the author and lead presenter of the ground-breaking, globally recognised Advanced Certificate for the Executive Assistant: ACEA® program. Richard also sits on the editorial board of Lucy Brazier OBE's Executive Support Magazine.
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