One common misconception is that success with AI comes from finding the "perfect” prompt. While prompts certainly matter, the biggest factor influencing AI output is actually the quality of the information you provide.

Think of AI as if you were onboarding a brand-new Executive Assistant. If you simply asked them to "summarize my week," they would have very little context about your priorities, your projects, or what actually matters to your executive. The result would probably be a generic summary that doesn't provide much value.

The same principle applies to AI.

The more relevant and organized context you provide, the more useful the output becomes. Whether you use Claude, Gemini, Microsoft Copilot, ChatGPT, or another AI assistant, the principle remains exactly the same.

If you remember last week's newsletter, we introduced the concept of AI connectors and integrations - the secure connections that allow AI to access information from applications like Gmail, Outlook, your calendar, project management tools, CRM, and collaboration platforms.

This week's prompts build directly on that foundation.

For AI to generate a meaningful Executive Context Brief, it first needs access to the information you're asking it to analyze. Depending on the AI platform you're using, that access may come through native integrations (such as Microsoft 365 Copilot, Google Gemini for Workspace, Slack AI, or HubSpot Breeze), automation platforms like Zapier, Make, or n8n, or by manually providing the information yourself.

One practical workflow that many Executive Assistants can adopt is creating a Weekly Executive Context Brief every Friday afternoon. Rather than allowing Monday morning to become a scramble, this workflow encourages spending a few minutes every Friday collecting the information that matters most while it is still fresh.

This workflow is best viewed as a repeatable system rather than a one-size-fits-all template. Every executive works differently, every organization uses different software, and every Executive Assistant supports unique priorities. The workflow should evolve alongside the executive's needs

Step 1: Review the Week Ahead

A typical Friday routine might include reviewing the executive's calendar for the upcoming week. Look for meetings that require preparation, back-to-back appointments that leave little room for transitions, travel schedules, customer meetings, presentations, or potential scheduling conflicts.

Step 2: Gather Your Context

Review your inbox and identify conversations that still require action. If your organization uses Microsoft Outlook, Microsoft 365 Copilot can quickly summarize long email threads, identify action items, and highlight messages that may require your attention. If your organization uses Google Workspace, Gemini for Workspace offers similar capabilities within Gmail by summarizing conversations and surfacing key information.

If your organization uses collaboration platforms such as Slack, Microsoft Teams, or Google Chat, consider reviewing conversations tied to your executive's highest-priority initiatives. Instead of asking AI to summarize every conversation, provide only the channels or discussions that are directly relevant to the coming week.

Project management systems such as Asana, ClickUp, Monday.com, or Notion can provide another important layer of context. Review upcoming deadlines, overdue tasks, blockers, and milestones that may affect your executive's priorities.

If your organization uses a CRM such as HubSpot or Salesforce, review any important client developments, major opportunities, upcoming renewals, or significant relationship updates. HubSpot's Breeze AI can help summarize contact activity, CRM records, and engagement history, while Salesforce's built-in AI capabilities can surface account insights, summarize opportunities, and highlight important customer updates.

Rather than manually reviewing every record, use these built-in AI features to quickly identify the developments your executive should know before walking into Monday morning. Those insights can then become an important section of your Weekly Executive Context Brief.

Step 3: Generate Your Executive Context Brief

Now paste the prompt below to create a weekly executive context brief:

Or to identify outstanding commitments:

As you begin experimenting with AI workflows, remember that the goal is not to automate everything at once. The most successful AI implementations usually begin with a single, repeatable workflow that solves a real problem. Once that process is working consistently, you can gradually expand it to include additional tools and information sources.

It is also worth remembering that AI performs much better when information is organized before it reaches the model. Instead of pasting dozens of unrelated emails and notes into one prompt, separate your information by source or topic whenever possible. Giving AI structured inputs makes it much easier to produce structured outputs.

Finally, always keep yourself in the approval process. AI is excellent at gathering information, summarizing conversations, and identifying patterns. It should not become the final decision-maker, particularly when legal matters, client relationships, financial decisions, or executive communications are involved. Human judgment remains the most important part of every workflow.

Slack says conversation and thread summaries, plus huddle notes, are now available to all customers on paid plans, and its Slack AI add-on is no longer sold separately on the Slack website.

Notion’s AI product now includes Enterprise Search, custom agents, connectors, and meeting-note workflows across workspace content and connected apps, including Slack and Google Drive. That makes Notion especially relevant if you want one place to collect context before building the executive brief.

Microsoft 365 Copilot’s release notes show continued updates to Copilot capabilities, and Microsoft’s Copilot Studio updates now include agent memory, organizational-data access, and computer use automation for multi-step workflows. For EAs, this matters because it expands what can be automated across email, calendar, Teams, and related workstreams, especially for recurring briefing workflows.

Artificial intelligence is changing the way Executive Assistants work, but it is not changing what makes the role indispensable. The greatest value an Executive Assistant provides has never been the ability to manage calendars or organize inboxes. It has always been the ability to create clarity, anticipate needs, connect information, and help executives make better decisions.

AI can gather information, summarize conversations, and organize data in seconds. What it cannot do is understand organizational culture, recognize subtle priorities, build trusted relationships, or exercise sound judgment. Those remain distinctly human strengths.

The most successful Executive Assistants will not be those who simply adopt AI tools. They will be the ones who thoughtfully integrate AI into their existing workflows, allowing technology to handle repetitive tasks while they focus on strategic thinking, relationship building, and executive partnership.

Let AI collect the information. Let your expertise create the insight.

That's it for this week.

This Friday, spend 20 minutes creating your first Executive Context Brief using AI. Pull together information from your calendar, inbox, project management system, collaboration tools, and CRM (or whichever tools you use), then use Prompt #1 to generate a one-page briefing.

Hit reply and tell us: What was the most valuable insight your Executive Context Brief uncovered? We'd love to hear how you're putting AI into practice.

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The Base Team