Using AI with your Executive is something a lot of EAs are already doing, but very few of us have actually agreed with our Executive how each of us should be using AI. And what we’re hearing from EAs in our community is that, without that conversation, EAs and Executives often end up using AI separately, with neither of them knowing what the other is doing.
A typical example goes something like this. An EA has set up an AI tool to put together a morning brief for their Executive, with the day’s meetings, the papers they need to read beforehand and the emails that need a reply. Meanwhile, their Executive has set up their own AI agent to triage their inbox and summarize the overnight emails. When they finally talk about how they’re each using AI, they realize they have both been building and checking versions of the same thing for weeks, and most of that work is something the EA could have handled from the start.
Working separately like this is easy to fall into, because most organizations haven’t given anyone much guidance yet. In Microsoft’s 2024 Work Trend Index, which surveyed around 31,000 people who work at a desk (so that includes most of us), 78% of people using AI at work were bringing their own tools, and 52% were reluctant to admit using it for their most important tasks. A 2025 study by KPMG and the University of Melbourne of more than 48,000 people found that only 40% said their workplace had clear guidance on generative AI.
So what to do? Have one short, practical conversation, and write down what you agree.
This isn’t just another AI list; it’s a collection of prompts written by Assistants, for Assistants, to help you get the most out of ChatGPT and start making a real difference in your day-to-day.
Doing the same work twice is the most obvious problem, but there are others too. A lot of what AI does well for an Executive, like morning briefs, inbox triage, meeting prep and follow-up actions, is work that naturally belongs with the EA. If your Executive builds those workflows themselves, they spend their time setting them up and checking the results, and they miss out on what you add, such as knowing which emails are actually urgent and which senders always need a same-day reply.
There is also the question of risk. If you and your Executive are using different tools with different rules about what goes into them, it can be very hard to know where confidential information has ended up. Agreeing how you’re using AI with your Executive means you’re both working from the same set of rules, and agreeing those rules usually means you can use AI for more of your work with confidence, rather than less.
Before you talk to your Executive, check what your organization already allows. Find out which AI tools are approved, whether there are rules about what kind of information can go into them, and whether your Executive has access to anything you don’t, such as Copilot built into their Outlook.
If there’s no policy, you can still agree your own rules, and it’s worth letting IT know which tools you’re both using. IT would much rather hear about those tools from you now.
This is the practical part, and most of this conversation can be covered in twenty minutes. Here’s what to agree:
The easiest way to start using AI with your Executive in a more joined-up way is to bring a specific proposal rather than an open question. Open questions are easy to say no to, or to put off until next week.
Instead of asking:
“Are you OK with me using AI?”
Try:
“I’d like to take over your morning brief using Copilot. Every morning by 7:30, you’d get your meetings, the papers to read, and the emails that need you, and I’ll check every name and figure before the brief reaches you. Nothing from the board pack or HR would go into the AI tool. Are you happy with that, and is there anything you’re already using AI for that I could take off your plate?”
Can you see the difference? The first question puts the decision back on your Executive with no detail. The second shows them exactly what they’ll get and what you’ll check, and that last question is often the one that uncovers the work you have both been doing twice.
Once you have agreed how you’re using AI with your Executive, write what you’ve agreed in a few lines and keep that note with any other working agreements you have, such as your communication principles. The note doesn’t need to be formal, as long as you can both find it easily.
Then come back to the agreement when something changes. A new tool or a change to your role are both good reasons for a review, and the tools are changing quickly enough that a check every few months is probably sensible.
If you haven’t had this conversation yet, start by making a list of everything you currently use AI for, and take that list to your next one-to-one.
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