ChatGPT Prompts for Executive Assistants: Emails, Calendars, Travel, and Chief of Staff Work

Executive assistants write more than almost anyone else in an organisation. Emails on behalf of senior leaders. Meeting prep documents. Travel itineraries. Board summaries. Draft responses that need to sound like someone else. The work is high-volume, high-stakes, and often invisible.

AI doesn't replace an EA's judgment, discretion, or institutional knowledge. But it eliminates the blank-page problem and the time drain of starting every document from scratch. This guide covers the prompts that make EA workflows faster.

ChatGPT Prompts for Writing Emails on Behalf of an Executive

One of the core EA skills is writing in someone else's voice. AI can draft emails in a specified tone and style — you review, adjust, and send.

Example prompt:

Write an email from [CEO Sarah Chen] to [the leadership team] announcing [a change to the Q3 planning process — we're moving from a 3-day offsite to a series of 4 focused half-day sessions over two weeks]. Key points to include: [the change is designed to reduce travel burden and increase quality of discussion; the dates will be shared by the end of this week; feedback is welcome but the decision is made]. Tone: [Sarah is direct, warm, and doesn't over-explain — keep it under 150 words, no bullet points].

The more you can characterise the executive's voice — formal or casual, long or short, how they open and close emails — the better the output. Over time, you build a style reference you can include in every prompt.

Tips for Voice-Matching

• Include 2-3 example sentences the executive has actually written
• Specify what they don't do (e.g., "doesn't use exclamation marks", "never starts with 'I hope this finds you well'")
• Ask for a draft, then a revised version that's 30% shorter — often the shorter one sounds more like them

Meeting Prep: Briefing Documents and Agendas

Senior leaders walk into dozens of meetings a week. EAs who prep them well save real time and reduce embarrassing gaps.

Example prompt:

Write a one-page briefing document for [CEO Sarah Chen] ahead of [a 30-minute intro call with the CFO of a potential acquisition target, TechFlow Inc]. Include: [background on TechFlow — B2B logistics software, $18M ARR, 80 employees, Series B; key strategic fit for us; suggested objectives for the meeting; 3 questions Sarah should consider asking; any known sensitivities]. Format: [scannable — headings and short paragraphs, printable on one page].

The briefing doc format is reusable across all meeting types. Build a template, adjust the specifics each time.

For recurring meetings:

Write a standing meeting agenda for [Sarah's weekly 1:1 with her direct reports, 30 minutes each]. Structure: [5 min — their wins and blockers this week, 10 min — open discussion / coaching, 10 min — decisions and priorities for next week, 5 min — anything else]. Include a reminder note at the top to review any outstanding action items before the meeting.

Travel and Logistics Coordination

Travel planning is still one of the most time-consuming EA tasks. AI speeds up the drafting, confirmation, and itinerary work.

Example prompt:

Create a travel itinerary for [Sarah Chen] travelling from [London Heathrow] to [New York JFK] for [a 3-day board meeting]. Trip dates: [Monday 14 April, returning Thursday 17 April]. Hotel: [The Beekman, Tribeca]. Meetings: [Board meeting Tuesday 9am–5pm at 99 Park Ave; dinner with the chairman Tuesday evening; working lunch Wednesday noon at the hotel]. Format the itinerary as a day-by-day schedule with local time, addresses, and notes on transit between locations. Flag any gaps where she may need transport arranged.

Use this as the starting scaffold. Fill in confirmed flight details and add any specifics. The format is consistent and easy to update.

Drafting Responses to Sensitive Emails

Some emails in the exec's inbox require a careful response — complaints, media enquiries, investor questions, HR escalations. AI can help you draft language that's measured and appropriate.

Example prompt:

Draft a response from [CEO Sarah Chen] to [an email from a long-term enterprise customer who is threatening to cancel after a major product outage last week]. The customer is upset but hasn't cancelled yet. Key messages: [acknowledge the impact without over-apologising; explain that a full post-mortem is complete and the root cause has been addressed; offer a 30-day service credit; ask for a call this week to discuss]. Tone: [senior, accountable, forward-looking — not defensive or overly corporate].

Always review sensitive drafts carefully. The AI doesn't know the full relationship context — you do.

Board and Executive Communications

Preparing board materials, exec summaries, and investor updates often falls to EAs or chiefs of staff. AI helps with structure and language.

Example prompt:

Write an executive summary for [a 12-page board pack for Q1 2026]. Key points to cover: [revenue grew 22% YoY to £4.2M; gross margin improved 3 points; two key hires made in product and sales; Q2 priorities are customer retention and the EU market expansion; one risk to flag — the enterprise sales cycle has lengthened and we're watching pipeline closely]. Format: [3 paragraphs, no bullets, suitable for board members to read in under 2 minutes before the meeting].

For board decks, AI is best used for language and flow — not for the numbers or strategic narrative, which need to come from you or the exec.

Managing the Executive's Inbox

EAs often process and triage executive inboxes. AI can help draft holding replies, declutter requests, or write polite declines.

Example prompt:

Write a polite decline on behalf of [CEO Sarah Chen] to [a speaking request from a conference organiser]. Reason for declining: [schedule is full for the next 6 months]. Keep it short. Be warm but definitive — no room for negotiation or a follow-up ask. Suggest they consider [our VP of Product, James Okafor] as an alternative speaker.

Holding replies:

Write a brief holding reply for [an inbound partnership enquiry]. Sarah hasn't read it yet. Acknowledge receipt, say she'll review by end of week, and ask them to confirm that [their company name and what they're proposing] is the right summary of their ask. Keep it to 3 sentences.

Building Reusable Templates

The highest-leverage thing an EA can do with AI is build a template library once and reuse it forever:

• Email templates: Board comms, investor updates, client introductions, media holding replies
• Meeting templates: Agenda formats for 1:1s, all-hands, board meetings, client calls
• Travel templates: Itinerary format, hotel confirmation checklist, pre-trip briefing doc
• Document templates: Briefing one-pager, decision memo, action item tracker

Build each template with a prompt that's specific enough to produce a consistent result. Add example outputs. Share with the whole exec team.

What AI Can't Do for Executive Assistants

• Know the political dynamics in the room
• Read between the lines of an email the way you can
• Replace the discretion required for sensitive situations
• Make judgment calls about what the exec actually wants

The EA role is built on trust, context, and relationship. AI handles drafting and structure — you handle everything that actually matters.

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If you're a product manager, marketer, scrum master, or sales professional looking for a full AI prompt library for your role — explore the Workshift toolkits at workshift.store/toolkits →