How to Give Your Executive Assistant an AI Toolkit: A Practical Configuration Guide

For most executive assistants supporting senior leaders in UK organisations, the priority tools are:

Microsoft 365 Copilot, if the organisation has a licence. This integrates with Outlook, Teams, Word, and PowerPoint and is the most relevant tool for the day-to-day tasks an EA performs. Prioritise this if available.

Claude (claude.ai) for longer document work: drafting correspondence, preparing briefings, synthesising research. Claude handles long documents better than most tools and produces clean, professional prose.

ChatGPT for research tasks, particularly where real-time web search is needed (ChatGPT Plus with web browsing). Useful for preparing background briefings, researching contacts before meetings, and tracking news relevant to the executive's agenda.

Start with one tool and build competence before adding more. For most EAs, Copilot (if licensed) or Claude is the right starting point.

The most time-consuming AI configuration task for an executive assistant is training an AI tool to draft in the executive's voice. This investment pays back quickly.

Create a Claude Project (available on Claude Pro) for the executive. In the project instructions, include:

A description of the executive's communication style: formal or informal, concise or detailed, direct or diplomatic.

Examples of the executive's actual correspondence (anonymised where necessary) that the AI can use as style references.

Standing context: the executive's role, the organisation, the key stakeholders the EA communicates with on the executive's behalf.

With this configuration, an EA can ask Claude to draft correspondence with significantly less editing required. 'Draft a reply to [person] declining their meeting request but leaving the door open for future contact. Match the executive's usual tone based on the examples in this project.'

Update the project instructions when the executive's style preferences evolve or when new context becomes relevant.

Preparing briefings for senior leaders is one of the highest-value tasks an EA performs, and AI substantially accelerates it.

For external meetings: 'Research [person/organisation] and prepare a briefing note covering their current role, recent activities, any news in the last six months, and any known connections to [executive's organisation or agenda]. Format as a one-page briefing suitable for a senior executive to read in five minutes before the meeting.'

For board meetings: upload the board pack to Claude and ask: 'Identify the three items that require the most active engagement from the chair/CEO and prepare five lines on each: what is being asked, what the likely debate is, and what the executive should prepare to address.'

For speaking engagements: 'Research the event [name], the expected audience profile, recent themes in [relevant industry], and any known attendees who might be significant. Prepare a briefing that gives the speaker relevant context for their address and for networking conversations.'

These workflows replace several hours of manual research per week with shorter, higher-quality outputs.

Copilot in Outlook is the most directly useful AI tool for EA inbox management. Key applications:

Drafting responses to routine correspondence: 'Draft a reply to this email confirming the meeting, asking for an agenda, and checking whether [colleague] should be included.' Copilot can generate a first draft that needs only minor editing.

Summarising long email threads before the executive reviews them: 'Summarise this thread in three bullet points: what was decided, what is outstanding, and what action is required from [executive].'

Meeting preparation summaries: for recurring meetings, Copilot can pull together recent emails, Teams messages, and documents related to the meeting topic and summarise the current state before the executive joins.

For EAs not using Copilot, Claude and ChatGPT can perform similar drafting and summarisation tasks with copy-pasted email content, though this is slower than the Copilot integration.

Senior leader and EA should agree clear boundaries for AI use:

What can the EA send without the executive reviewing? AI-drafted routine confirmations and simple responses might be sent directly. Substantive correspondence on the executive's behalf should typically be reviewed before sending.

What information can the EA share with AI tools? Consumer AI tools should not receive commercially sensitive information, personal data about individuals, or confidential board matters. For sensitive correspondence, draft without names and specific confidential details, or use enterprise tools with appropriate data handling.

How should the EA flag AI limitations? If an AI-drafted response looks odd or the EA is uncertain about tone, it should be flagged rather than sent. EAs should treat AI output as a first draft, not a finished product.

A brief conversation between the senior leader and EA to agree these boundaries takes 30 minutes and prevents misunderstandings that could be harder to repair.