Hire an Executive Assistant with senior-level judgement

Define the level of support you need

Executive support ranges from scheduling and travel to acting as a chief of staff for operations. Decide whether you need an EA who executes instructions precisely or one who anticipates, prioritises and pushes back. Both are valid, but they require different experience and different candidates.

Share how you work

Write a short user manual about yourself: when you do your best thinking, how you prefer to receive information, who always gets access and which meetings you would rather avoid. This document saves weeks of trial and error and helps your EA make decisions in your absence.

Start with the calendar, then the inbox

Calendar ownership produces quick, visible wins and builds trust. Once it is running smoothly, introduce inbox triage with clear categories, such as action required, information only and delegated. Only then move to drafting and sending on your behalf for routine correspondence.

Agree confidentiality boundaries

Be explicit about what is confidential and how sensitive material should be handled. Use secure document sharing, restrict access to the minimum required and agree how personal and business matters are separated. Clear boundaries protect both you and your assistant.

Review the partnership monthly

A short monthly review covering what is working, what is not and what to hand over next keeps the role growing. Many leaders find their EA takes on considerably more within the first quarter once the foundations are in place.

A sample job summary for an executive assistant

A clear summary might read: we are seeking an experienced executive assistant to support our managing director, owning a complex calendar, preparing briefing notes for meetings, coordinating board papers and managing travel across Australia and overseas. You will act with discretion, anticipate needs and keep commitments moving. This role suits someone who has supported senior leaders before and enjoys bringing order to a busy schedule. Even if we run the search, writing this summary forces useful decisions about scope, seniority and the hours that must overlap.

Red flags when hiring an executive assistant

Be wary of candidates who describe the role purely as task execution, who cannot give examples of anticipating a leader's needs or who speak loosely about confidential information from previous roles. Discretion shows in how candidates talk about past employers. Also watch for discomfort with pushing back: an executive assistant who never says no will struggle to protect your time. The strongest candidates describe how they shaped calendars, prepared leaders and closed loops, not just how many meetings they booked.

What a good first week looks like

In the first week, your executive assistant gains delegated access, reviews your calendar for the next month and meets key people you work with, at least by introduction. They prepare briefs for two or three upcoming meetings so you can calibrate the level of detail you prefer. A short daily check-in covers decisions and preferences. By the end of the week, they should own scheduling requests and travel, and you should already notice fewer coordination messages in your inbox.

Remote versus in-house executive support

Senior leaders sometimes assume executive support must be in the office. In practice, most executive assistant work is digital: calendars, email, documents, travel bookings and video meetings. A remote EA can do all of this effectively, with occasional in-person needs handled through local services or your team. The managed model adds continuity, because cover is arranged during leave, and access to AI tools that speed up briefings. In-house support still suits roles that involve physical office management or frequent face-to-face hosting.

Measuring your executive assistant's impact

Executive support is best measured by its effect on your week. Track hours of protected focus time, the share of meetings that start with a prepared brief, the number of open actions closed on time and how often you personally handle scheduling or travel. Ask a few key colleagues each quarter whether working with you has become easier. Together, these signals show whether your assistant is multiplying your time or simply processing tasks.

Interview questions to ask a executive assistant

1. How would you protect two hours of focus time each day in a packed calendar?
2. Describe how you prepared an executive for an important meeting.
3. Tell me about a time you had to say no to a senior stakeholder.
4. How do you track actions across many meetings?
5. How have you handled confidential information in previous roles?
6. Walk me through planning a multi-city business trip.
7. How do you use AI to summarise long documents accurately?
8. What do you need from an executive to do your best work?

A 30, 60 and 90 day plan for your new executive assistant