No, AI will not replace executive assistants. That was the first thing Chris Colston addressed in a recent Pally Talk training session on using Claude, the AI assistant built by Anthropic, in real EA, PA, and VA workflows. It is also the first question Chris says he gets asked at almost every industry event he attends, and it is a completely understandable one given how much attention AI has received recently.
Here is what EAs actually need to know before deciding whether, and how, to use it.
AI is an assistant to the assistant, not a replacement
Chris has spent the last six months working full time helping executive assistants and their principals set up AI systems, after years of using it in his own marketing career. His framing is simple: think of Claude as an assistant to the executive assistant, not a replacement for one.
What it takes off your plate is the admin layer underneath your actual role: the writing up, the chasing, the cross referencing between a diary and an inbox that never happens automatically. That frees you to spend your time where your principal actually needs a person, whether that is judgement calls, relationship management, or handling something sensitive in person.
It is not perfect, and it should never be fully trusted
The second point Chris was clear about is just as important as the first. AI gets things wrong. He describes it as “the worst it will ever be,” meaning it improves constantly, but that also means today’s output should never go anywhere without being checked first. Every draft, every summary, every suggested reply should be reviewed and approved by you before your principal ever sees it. You stay in charge of the AI, not the other way around.
You do not need to connect any of your tools to get started
A common misconception is that using Claude properly means connecting your entire inbox, calendar, and project boards from day one. It does not. Chris demonstrated multiple real EA tasks, including turning a messy travel brief into an itinerary and prioritising a crowded inbox, using nothing more than information pasted directly into a chat. No tools connected, no principal’s name required if you would rather keep it vague.
If you and your principal do decide connecting tools is worth it, that is where the bigger time savings show up. One of Chris’s clients receives a weekly briefing pulling together their sales pipeline, accounting, and inbox automatically, and reports getting roughly 20 percent of their time back as a result.
What actually happens to your data
Privacy is understandably a serious concern when you are working with confidential, high net worth, or otherwise sensitive information. Claude has a model training setting that can be switched off. With training turned on, conversations may be used to improve the model and retained for up to five years. With it turned off, conversations are kept for 30 days, and anything you delete is not used for training. Content flagged for a safety review may still be checked either way. It is worth reviewing this setting, along with Claude’s wider privacy policy, before pasting in anything sensitive, in the same way you already would with any platform you trust with client or business information.
For teams, there are also company wide setups available, where a principal, driver, chef, or wider household team can all work from the same connected system rather than everyone working in isolation.
Frequently asked questions
Does Claude ever go down, and what happens if it does? Like any platform, outages happen occasionally. Chris’s advice is not to rely on AI as your only system. Keep your existing tools such as Asana, Monday, or your email client running in parallel so you are never stuck if Claude is temporarily unavailable.
Why does connecting other platforms use up credits so quickly? Usage tends to spike at peak times of day. Turning off features like web search or extended thinking when you do not need them, starting new chats for new tasks rather than one long ongoing thread, and unticking tools you are not using in a given conversation can all help manage usage.
How does Claude compare to ChatGPT for this kind of work? Both can handle similar EA style tasks and offer comparable project style features. Preference often comes down to interface and how you like to work, rather than one being clearly superior for this use case.
Pally Talk runs regular training sessions like this one for EAs, PAs, and VAs who want practical, real world guidance on using AI well and safely. If this is useful, get in touch to find out about upcoming sessions.
Get in touch to be connected with Chris, admin@pallytalk.com