You’re mid-task. The email is half-drafted, the schedule won’t reconcile, or your executive just asked you to turn a chaotic briefing into something coherent, and you’ve hit a wall. AI won’t replace your judgment, your discretion, or the trust you’ve spent years earning. But used well, it can be the colleague who unsticks you, quickly, without the small talk. Here are five ways to put it to work.

1. Draft the email you don’t know how to start

Tone is everything at this level. An email to a board member lands differently than one to a vendor, and getting it wrong can create friction that your executive has to spend political capital smoothing over. When you’re staring at a blank page, give AI the context: who it’s going to, what the desired outcome is, and what relationship dynamic matters, and ask for a draft.

The first version won’t be right. It never is. But it gives you something to push against, which is far faster than starting cold. Edit for voice, trim the hedging, and send something you’d be proud to have your name on.

TRY ASKING: “Draft a brief, warm reply declining a meeting request from a long-term contact. The tone should be personal but firm. My executive has capacity constraints through Q3.”

2. Turn a data dump into a readable briefing

Your executive has 12 minutes before a call with someone they haven’t spoken to in two years. You have a LinkedIn profile, an old email chain, a news article, and a conference bio. Pasted together, that’s not a briefing, it’s noise. AI can synthesize it into the three things your executive actually needs to know: what the person does now, what’s changed, and what the likely agenda for the conversation is.

You’re not outsourcing the analysis. You’re compressing the formatting work so you can spend your time on the interpretation that only you can do.

TRY ASKING: “Here’s background on [Name] ahead of a 15-minute introductory call. Summarize in three bullet points: current role and focus, any recent news worth referencing, and one likely topic they’ll raise.”

3. Think through a tricky situation out loud

Sometimes what you need isn’t a deliverable, it’s a sounding board. You’re managing a scheduling conflict that’s going to upset someone regardless of how it’s handled, or navigating a request from a family member that cuts against how the household runs. These are judgment calls, and the judgment is still yours.

But talking through the options, even with an AI, helps externalize the problem. Describe the situation, the constraints, and the relationships involved. Ask what considerations you might be missing. You’ll often find that by the end of typing it out, you’ve already worked out what to do.

TRY ASKING: “Help me think through a scheduling conflict. I have two back-to-back commitments that can’t both be held, and both parties are important to manage carefully. Here’s the situation…”

4. Tighten a document that’s one draft too long

You’ve received a report, proposal, or memo that’s 14 pages when it should be 4. Your executive isn’t going to read it. Your job is to get them to the decision point without losing anything important. This is exactly the kind of task that AI handles well: paste the document, specify the audience and purpose, and ask for a condensed version that preserves the key findings and the recommended action.

Review the output carefully; you’re checking for what got cut that shouldn’t have been. But the initial compression work takes minutes instead of an hour.

TRY ASKING: “Condense the following into a one-page executive summary. The reader is time-pressed, needs to understand the recommendation, and will likely only ask one follow-up question. Prioritize accordingly.”

5. Build a checklist for something you’ve never handled before

First-time tasks are where experienced EAs can still get caught out. Coordinating a family office meeting you’ve never run before, managing the logistics of a private medical appointment in another city, handling the arrangements for an estate matter, these are high-stakes and low-margin-for-error. AI can give you a working checklist of everything that typically needs to be managed, which you then interrogate and adapt to your specific situation.

You’re not following it blindly. You’re using it to make sure you’re not missing the thing you didn’t know to ask about.

TRY ASKING: “I’m coordinating [type of event/task] for the first time. Give me a comprehensive checklist of everything that typically needs to be arranged, from early logistics through to day-of details and follow-up.”

A few important things to keep in mind: don’t put sensitive personal details, confidential client information, or private correspondence into any AI tool without understanding your employer’s data policies. The prompts above are frameworks; what you share in them is your call.

AI works best when you know exactly what you need. Better input is better output and the fact that you’re asking the right question is still the skill that matters most.

Recognized by Forbes as one of America’s Best Professional Recruiting Firms for 2024, 2025 & 2026, as well as by Business Insider America’s Top Recruiting Firms and Inc Magazine’s PowerParter’s List, Pocketbook Agency is an award-winning boutique recruitment firm placing exceptional, high-level administrative and support roles across the US in both corporate and domestic settings. If interested in working with us or for additional inquiries, please reach out to [email protected].

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