How to hire an executive assistant, step by step
An executive assistant sees nearly everything you do, from your calendar to your inbox to your family logistics, so a casual hiring process carries real risk. These steps run from defining the job to the first month together, and each one tests for the judgment the role depends on.
Decide which role you need
Titles blur, so start with the work. List the tasks you want off your plate and the decisions you would like made without you, then match them to a role.
If you need someone to own your calendar and protect your time, you are hiring an executive assistant. If you mainly want a thinking partner who runs initiatives, that is a chief of staff, and the pay and profile differ sharply.
- Executive assistant: supports one or a few leaders with calendar, email, travel, meeting preparation and gatekeeping.
- Administrative assistant: keeps an office or team running, with scheduling, supplies, records and general support.
- Virtual assistant: remote and often part time or freelance, best for defined tasks rather than a close partnership.
- Chief of staff: a strategic role that drives priorities and projects across a leadership team, usually without administrative work.
Write the job description around outcomes
Describe what success looks like instead of stacking adjectives. Saying the assistant keeps your calendar aligned with your top three priorities and flags conflicts a week ahead tells candidates far more than calling for someone detail oriented. Name the tools they will use daily, such as your email and calendar platform, travel booking and expense software.
Be explicit about confidentiality, and say whether you will ask for a nondisclosure agreement. Several states and cities, New York among them, require a good-faith pay range in job postings, so settle the range before you publish.
- Three to five outcomes the role owns.
- The tools, systems and time zones involved.
- Travel, after-hours and on-call expectations.
- Confidentiality requirements.
- Reporting line, location and pay range.
Research pay with market data
Pay for executive assistants varies widely by city, industry and the seniority of the executive. Use more than one source. The U.S. Bureau of Labor Statistics publishes wage data by metro area for executive secretaries and executive administrative assistants, and recruiters and salary surveys add current local detail.
Price the job you described, not the title. An assistant supporting a chief executive across time zones, with personal and family logistics on top, commands more than one supporting a department head during office hours. Many states and cities, including New York, bar employers from asking candidates about their pay history, so build the offer from the role itself.
Interview with real work samples
Ask finalists to complete short exercises that mirror the job, keeping each under an hour or paying for longer ones. Watch how they ask clarifying questions as closely as you judge the result.
In interviews, probe discretion and prioritization with real scenarios. Ask what they did when someone pressed them for information they could not share, how they chose between two urgent requests, and when they last pushed back on an executive’s plan.
- A calendar puzzle: three conflicting meeting requests across two time zones and a delayed flight, resolved and explained.
- An email draft: decline an invitation from an important contact while keeping the relationship warm.
- A summary: turn a long email thread into five lines and a list of decisions needed.
Check references and backgrounds with consent
Ask to speak with executives the candidate supported directly, not only HR contacts. Specific questions work best: how did they handle a sensitive situation, what did you stop worrying about once they joined, and what do they need from a new manager?
A background check ordered from a screening company falls under the Fair Credit Reporting Act. You need the candidate’s written authorization after a clear disclosure, and before rejecting anyone based on the report, you must share a copy and a summary of their rights. Some places also limit when you may ask about criminal history; New York City, for example, generally bars those questions until after a conditional job offer.
Onboard deliberately in the first 30 days
Set up access before day one: delegated email and calendar permissions, travel and loyalty profiles, expense tools and a password manager for shared logins. A slow start on access wastes the weeks when a new assistant is most eager to learn.
Write a preferences document covering how you like meetings scheduled, how you travel, who always gets through and which topics you handle yourself. Then agree on decision rights in plain terms, and meet briefly every day for the first two weeks before shifting to a lighter rhythm.
- Meetings the assistant can accept, decline or move without asking.
- Spending they can approve, and up to what limit.
- Messages they can answer in your name, and in what tone.
- Situations that justify interrupting you.
Build the partnership over time
Keep a weekly one-on-one on the calendar and protect it. Use it to look ahead at the next two weeks, review what slipped and widen decision rights as trust grows.
Make feedback run both ways. Ask what slowed them down, which of your habits create extra work and what context they are missing. Invite your assistant to planning meetings where they can hear priorities firsthand, and revisit the role every six months as they take on more.