The wrong question is doing a lot of damage.

The question isn't whether AI can do the tasks. It's whether you can afford to lose the judgment.

^{Girl at a typewriter - Museums of History New South Wales}

^{If you’re on the go and would rather listen to the article you can do that here.}

Another week, another piece asking whether AI will replace EAs and PAs. I’ve read three versions of this article in the last month alone and they all follow the same structure. Here are the tasks AI can now do. Here is a list of EA responsibilities. Look how much overlap there is. Isn’t that worrying?

I want to be direct with you because this framing isn’t just wrong, it’s potentially costing you something real. If you’ve read one of these pieces and thought “maybe I don’t need that hire,” you’ve made a decision based on a model of the role that simply doesn’t exist.

Here’s what those articles never account for, they list the tasks but they never model the judgment and the judgment is the entire job.

I placed an EA last year with a founder who had genuinely convinced himself he’d been managing fine with AI tools for months. His calendar was pretty clean, his emails got answered, meetings got booked and everything mostly ran smoothly on the surface. What he told me a few months after the hire was that he hadn’t realised how much he’d been white-knuckling it. How many micro-decisions he was still holding and how much cognitive load he had just silently absorbed. The EA took it and not because they followed a process but because they read him.

That’s what a great EA does. They run a continuous, live read on you and on your energy, your capacity, your blind spots and patterns and they make decisions based on that read that nobody else in your business is positioned to make. AI doesn’t have a relationship with you. It doesn’t know that the Wednesday board call needs to move because you get a migraine when you fly on Tuesday nights. It doesn’t know that a particular investor triggers a defensiveness that costs you thirty minutes of recovery time. It doesn’t know that you need twenty minutes alone before a pitch, not just a briefing document.

A great EA knows those things because they have been paying attention for months, with actual stakes.

I’m not arguing against AI here at all, the best EAs I know are using it constantly. Scheduling tools, summarising, drafting documents, building systems. They are genuinely more effective because of it but that’s exactly the point. The tool augments the judgment but it doesn’t replace it.

So the right question isn’t “will AI make my EA redundant?” The right question is do you have someone in your business whose job it is to protect your capacity and make calls you’re not going to be across? If the answer is no, whether that’s because you never hired that person, because you let them go or because you convinced yourself a stack of tools was the same thing then you’re probably

carrying weight you shouldn’t be carrying.

AI is very good at organising a schedule but it cannot reshape one based on how you are actually coping that week. That gap is not closing. That gap is the job.

I’d love to know whether any of this resonates with where you are right now. Hit reply and tell me.

Until next time, Henrietta