An executive assistant is hired for judgment, not administrative speed. Define what the executive should stop doing, then test decisions: a double-booked calendar with competing stakeholders, an inbox to triage, a trip that collapses mid-journey. Referrals and assistant networks beat job boards for this role, and the final call belongs to the executive who will work with them daily.
Trust-dependent roles travel through networks, not adverts. The best route is a referral from another executive assistant or from a senior leader whose assistant has just moved on. Assistant communities, professional associations and the alumni networks of large employers all produce candidates who are quietly open to the right role while being entirely uninterested in the market generally. Specialist agencies earn their fee here because the pool is relationship-held rather than published. Chiefs of staff and senior office managers looking for narrower, deeper work are worth approaching directly. Run the search discreetly if the incumbent is still in post. Publish a precise [executive assistant job description](/job-descriptions/executive-assistant) even for a referral pipeline, because ambiguity about scope is the single most common reason these hires fail.
Name the executive and the decision rights. Candidates need to know whose calendar they hold, whether they may decline meetings on that person's behalf, what spending authority comes with the role, and how much confidential material passes through their hands. Say whether personal and family logistics are included, because discovering that after starting is a common cause of early resignation. Describe the travel pattern and the realistic hours around board meetings and results periods. Be clear about whether the role sits alone or inside an assistant team, and whether it can grow toward chief of staff. Assistants at this level choose the executive as much as the company, so describe how that person works: pace, communication style and what they find most difficult to delegate.
Give them a conflict with no right answer. A useful exercise: the executive is double-booked between a board member, an unhappy customer and an internal review that took a month to arrange, a flight has moved, and two of the three parties have already been rescheduled once. Ask what they would do and, more importantly, why. Strong candidates ask about relative priorities, propose a sequence, name who they would call personally, and say what they would tell the executive afterwards. Weak candidates simply pick one. Follow it with an inbox triage of a dozen real-looking messages. Then use focused [executive assistant interview questions](/interview-questions/executive-assistant) about a time they overruled or challenged the person they supported.
The executive must be in the room, early. Chemistry is not a soft consideration in this role; it is the job. Run a short working session rather than a formal interview: walk through a genuine week, let the candidate ask how the executive prefers to be interrupted, and watch whether they probe or simply agree. Add a scenario debrief with a second senior leader, and a conversation with the assistant team or office manager they will coordinate with daily. Coordinating three senior diaries is itself a test of your own process, and [interview scheduling software](/interview-scheduling-software) keeps it from slipping. Reference the people the candidate protected, including peers and junior staff, not only former bosses.
Expect a longer search than for other administrative roles. Experienced assistants are candidate-short in most markets, they move rarely, and they are selective because a bad executive match makes the job miserable. Referral-led searches move faster than advertised ones but still take time to surface the right person. Keep everything visible in an [applicant tracking system](/ats) so a quiet pipeline does not stall unnoticed. Close on the relationship rather than the package: autonomy, the executive's willingness to actually delegate, the stability of the role, and how decisions get made. Assistants who leave usually cite being micromanaged or kept away from real information, so address both directly in the final conversation.
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