12 strategies to work more effectively with your executive assistant

Executive overview

Most founders hire an assistant but never fully delegate — they stay in the loop on email, own their calendar, and handle travel coordination themselves. The result is stress without relief.

The fix is treating your assistant as the owner of your time, not a task executor. Four pillars make this work: inbox, calendar, travel, and communication rhythm.

Your inbox is a public to-do list for strangers; your assistant's job is to own it entirely.

Inbox management

• Create a folder structure including a review folder where the assistant parks anything unresolved
• Hold a daily meeting to scan the review folder, the task list, and sent replies — this is how you train them
• Build an inbox SOP: as the assistant handles scenarios, document responses as reusable templates
• The SOP compounds over time — future assistants inherit the full playbook

Calendar ownership

• Define a perfect week: give your assistant time blocks for sales calls, team meetings, gym, family — they schedule within that scaffolding
• Do a calendar complete review every Sunday: the week ahead should be fully populated with context before you add your own priorities
• Add rich notes to every invite — links, prep materials, copied emails — so you can ramp up in seconds before any meeting
• For meetings booked via Calendly or third-party links, create a parallel "notes" entry with full context alongside it

Travel coordination

• Use a preloaded year: a single one-page document showing every month as dots, highlighting travel, events, and family commitments — shared with your partner
• Create trip files: a Google Doc per trip with accommodation, transport, agenda, and links — referenced from all calendar entries
• Run a weekly sync with your assistant and partner to scan the next 2–3 weeks, resolve childcare conflicts, and align schedules before they collide

Communication rhythm

• Run a daily sync with your assistant to give context on emails, decisions, and relationships — this is how they build a context map of your world
• Use rerouting: when someone messages you on the wrong channel (SMS, WhatsApp, DMs), screenshot it, loop in your assistant, and move the thread to email — this trains contacts over time
• Implement closing the loop: at the end of each day, the assistant posts a Slack summary of everything completed or moved forward — you scan it only when you have a question, not as a check-in