The Calendar Group

Hiring guide

Executive Assistant

Senior-level support for an executive's working life — calendar, communications, and the judgment behind both.

Begin a search for this role(877) 404-5290

Compensation

$90,000–$160,000 base

Typical base compensation, major U.S. markets, 2026. Scope, travel, and household complexity move the range.

We advise on offer structure — schedule, housing, benefits, bonus — before every search. The right package is how great people stay.

An exceptional executive assistant changes what a leader can carry. The calendar reflects strategy instead of whoever asked loudest. Meetings begin prepared and end with owners. Correspondence goes out in your voice, travel bends around your energy rather than the airline's schedule, and the thirty small decisions that used to reach you now get made — correctly — one level down.

At the senior level, the role is a thinking partnership. A great EA understands the business well enough to protect your time from the merely urgent, drafts in your register, reads the politics of a meeting request, and represents you to boards, investors, and direct reports with exactly the right weight. The keyboard skills are assumed; the judgment is the job.

We place EAs who have supported principals at the top of their organizations and have the references to prove it — long tenures, executives who followed them between companies, and specific stories of trust extended and honored. When we present a short list, every name on it has already cleared that bar.

What the role owns

  • Strategic calendar management aligned to the executive's actual priorities
  • Meeting preparation — briefings, materials, agendas, and follow-up tracking
  • Correspondence drafted and managed in the executive's voice
  • Complex travel planning across time zones, with contingencies built in
  • Gatekeeping and triage of requests, meetings, and communications
  • Board meeting logistics and materials coordination
  • Expense management and administrative operations for the executive's office
  • Liaison with leadership teams, assistants, and external stakeholders

What great looks like

A great EA runs the calendar as an editor, not a clerk — declining, shortening, and combining meetings so the week reflects what the executive actually said mattered this quarter.

Her drafts go out with light edits or none, because she has absorbed the voice — the phrases her principal uses, and the ones he never would.

She sees around corners: the briefing for Thursday's difficult meeting includes the history with that counterpart and the question likely to come up in the last five minutes.

Other executives' assistants trust her, which quietly gets her principal better slots, earlier intelligence, and favors that never appear on any org chart.

When she is out for a week, the seams show — and when she returns, the backlog is cleared by Tuesday.

Interview questions worth asking

  1. 01

    Walk me through how you managed your last principal's calendar — what did you decline on your own authority, and how did you decide?

  2. 02

    Show me how you prepare an executive for a high-stakes meeting. What is in the briefing, and how long is it?

  3. 03

    Tell me about a time you caught a mistake — yours or your principal's — moments before it went out. What happened?

  4. 04

    How do you handle a board member or major investor who wants time your principal does not want to give?

  5. 05

    Describe the working relationship with the best executive you supported. What did they delegate that surprised you?

Questions

Hiring an executive assistant, answered.

How is an executive assistant different from a personal assistant?
An EA supports a professional role — the executive's calendar, meetings, communications, and stakeholders inside a business context. A personal assistant supports a life: home, family, travel, and personal affairs. Many senior principals need both kinds of support, and some hires span the two. If the majority of the work involves the company, hire an EA; if it involves the household, hire a PA; if it is genuinely both, say so up front.
What distinguishes a senior EA from a good administrative assistant?
Judgment exercised independently. An administrative assistant executes defined tasks well. A senior EA makes calls in the principal's name — which meeting to decline, how to phrase the sensitive reply, what can wait until Monday — and gets them right. In interviews, listen for decisions made without asking, and what happened when one was wrong. Candidates who have only ever executed instructions will describe processes; senior EAs describe choices.
Should we hire from inside our industry?
It helps less than most executives expect. Industry vocabulary can be learned in a quarter; calendar judgment, discretion, and executive-level polish take years and transfer completely. The exceptions are heavily regulated or technical settings where context genuinely shapes daily decisions. We would generally rather present a superb EA from an adjacent industry than a middling one who knows your acronyms.
How do we assess EA candidates beyond the interview?
Simulate the work. Give finalists a realistic exercise — a conflicted calendar to untangle, an email to draft in your voice from bullet points, a travel scenario with a disruption — and review it together. How they think aloud matters as much as the output. Then let references carry real weight: prior principals, reached directly, asked what they delegated and what they would not. That conversation reveals more than any résumé.

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Looking for an executive assistant?

Tell us about the household and the role. A senior advisor — not a coordinator — will come back to you within one business day.

Held in confidence. No obligation.