If you are an EA, PA, or VA juggling four diaries, a scrappy voice note, and an inbox that never stops refreshing, you already know the real problem is not a lack of effort. It is that none of your tools talk to each other. Your calendar does not know what is in your inbox. Your Trello board does not know what your principal just mentioned on a call. Everything lives in a different place, and keeping it all connected is left entirely up to you.
This is exactly the gap that Chris Colston addressed in a recent Pally Talk training session on using Claude, the AI assistant from Anthropic, in real EA workflows. Chris works full time helping executive assistants and their principals set up AI systems, and his session focused on one simple idea: AI is not here to replace the assistant. It is here to be an assistant to the assistant.
Below are four real examples from the session showing exactly how Claude can be used for the tasks that eat up the most EA time: travel planning, diary management, meeting notes, and email.
Example 1: Turning a messy travel brief into a clear itinerary
Chris shared a real scenario: an email arrives late at night, cobbled together from several earlier messages. Four details are unconfirmed, preferences are buried in throwaway lines, and nothing tells you what to prioritise.
By pasting that email into Claude with a simple prompt such as “turn this brief into a two day itinerary, flag anything I need to chase, what I need to book, and anything that clashes,” Claude returned a clean breakdown: what needed deciding first, a day by day plan, what to book, what to chase, and what information was missing. It even flagged a scheduling clash the assistant had not spotted, because it cross referenced the new email against context already saved in the chat.
Example 2: Spotting calendar clashes across multiple diaries
Many EAs are managing more than one calendar at once: the principal, a spouse, a house manager, a driver. Fifteen commitments can arrive through email, text, and scribbled notes, with no single view of the whole week.
Chris asked Claude to review commitments across all four diaries, flag clashes, and separate what the assistant could fix alone from what needed a decision from someone else. Claude returned a prioritised list of decisions needed, items the assistant could resolve immediately, and gaps that were unconfirmed anywhere. This is the kind of task that normally takes real concentration to untangle by hand.
Example 3: Turning voice notes into clear actions
If you have ever received a five minute rambling voice note full of decisions, vague deadlines, and half finished commitments, you know how much mental effort it takes just to extract what actually needs doing.
Chris demonstrated this by pasting a voice note transcript into Claude and asking for decisions, actions with owners, anything unresolved, and any vague deadlines flagged clearly. What came back was a short, structured summary that turned a confusing ramble into a checklist someone could act on immediately, including catching that several “deadlines” were never actually confirmed.
Example 4: Prioritising a crowded inbox
A typical morning inbox might have twelve emails by 9am, with the most urgent one buried seventh from the top. Claude was asked to review the inbox, identify what needed action that day, what needed a decision from the principal or another named person, and what could wait. It surfaced the item with an actual deadline, grouped related decisions together instead of chasing them separately, and drafted holding replies where appropriate.
The real reason this works: context
None of this depends on luck or a lucky prompt. The reason Claude produced such specific, accurate answers is context. Chris built each example around a Claude project with background information already saved, including who people are, what has already been agreed, and what matters to the principal. Every new chat then starts from that shared understanding instead of from zero. As Chris put it, that is the difference between a tool you use occasionally and a system that actually works for you.
Frequently asked questions
Do I need to connect my email and calendar to use Claude this way? No. You can paste in information manually, exactly as shown in these examples, and still get useful results. Connecting tools like Outlook, Google Calendar, or Trello makes it faster, but it is entirely optional and worth discussing with your principal first.
Is my principal’s information safe? You control what you share. You can keep details vague, avoid using real names, and check Claude’s privacy settings before pasting anything sensitive.
Will this replace the EA role? No. It handles the admin layer, drafting, chasing, and cross referencing, so you can spend your time where your principal actually needs you.
If you want to see this demonstrated live, or learn how to set up your own Claude project with the right context saved, Pally Talk runs regular training sessions for EAs, PAs, and VAs just like this one. Get in touch to find out when the next session is running.