Founders Aren't Asking for an "AI Wizard": What They Want From Their Next EA

I have four Executive Assistant roles on at the moment. Not one founder has asked me to find an “AI wizard”. It has not come up in discovery, in the role brief or in conversations about onboarding. And when I screen candidates, “Can you build an AI agent?” is not at the top of my list of questions.

What I actually want to understand

When I speak to an EA, I want to understand how they work:

• How they make sense of competing priorities
• How they keep decisions and follow-ups moving
• How they organise information so it is useful, not just stored somewhere
• How they use tools to reduce repetitive work
• Where they know human judgement still matters

If AI is part of that, great. Show me where it helps.

A list of tools tells me very little

There is a big difference between these two answers.

“I use these six AI platforms.”

“Here is the problem I had, here is what I changed, and here is the difference it made.”

The second answer is the one I want to hear. It shows judgement, ownership and the ability to improve how work gets done. A tool list shows exposure. A described workflow shows impact, and it is far harder to fake.

Feeling behind before you have started

With so many people promoting AI courses, I worry that capable EAs are being made to feel behind before they have even looked at what they already do well.

This is not an argument against learning. A good course can be genuinely useful when it fills a specific gap. But if you are already using AI thoughtfully in your role, I would not rush to buy another one simply because your feed is telling you to catch up.

Start by mapping what you already do

Before you spend any money, map your existing workflows:

1. What have you simplified? Think of recurring tasks that now take a fraction of the time.
2. What have you automated? Include the small things: templates, rules, summaries, reminders.
3. What can you now do better? Look for improvements in quality, speed or consistency, not just effort saved.

Then identify what you actually need to learn. That gap, not a headline, is what decides whether a course is worth your time and money.

For founders hiring an EA

If you are hiring, it is worth asking the same questions. Rather than asking whether a candidate “knows AI”, ask them to walk you through a workflow they improved. You will learn far more about how they think, prioritise and follow through.

The bottom line

These four briefs are not the whole market. But they are a useful reminder: the founders I am speaking to want someone who can bring judgement, structure and follow-through. They are not asking their next EA to build AI agents.