The Calendar Group

Hiring guide

Personal Assistant

The person who runs your day so you can live it — calendar, travel, correspondence, and everything unassigned.

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Personal Assistant · New York$80,000Personal Assistant · Atherton, California$180,000

Compensation

$90,000–$150,000 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.

A personal assistant is the difference between managing your life and living it. The calendar that actually reflects your priorities. The trip booked around how you like to travel, down to the seat and the early check-in. The gift that arrived on time, the contractor who got a decision, the inbox that no longer follows you to dinner.

In a private capacity, the role reaches well past scheduling. Your PA handles correspondence and gatekeeping, personal purchasing, appointments, memberships, and the long tail of tasks that belong to no one else. She works across your household, your office, and your family — often the connective tissue among all three.

The hire is intimate by nature. This person will know your preferences, your finances in outline, your family dynamics, and your moods before coffee. Skills can be verified; the harder judgment is trust and fit — whether this particular person can sit inside your life for years and make it quieter. That is the judgment we have spent two decades refining.

What the role owns

  • Complex calendar management and scheduling across personal and professional commitments
  • Travel planning — flights, hotels, ground transport, itineraries, and contingencies
  • Correspondence, phone screening, and gatekeeping on the principal's behalf
  • Personal purchasing, returns, gifting, and wardrobe coordination
  • Appointments, reservations, and membership management
  • Household liaison — coordinating vendors, staff, and deliveries with the home team
  • Expense tracking, invoice review, and personal administrative filing
  • Special projects — events, moves, renovations, and whatever the season brings

What great looks like

A great PA answers the question you were about to ask — the itinerary already includes the backup flight, the dinner reservation already accounts for the allergy.

She gatekeeps without giving offense; people who were told no by her tend to hang up feeling well treated.

Her systems survive her vacation — preferences, contacts, and standing instructions are documented so thoroughly that a substitute could keep your life running for a week.

She spends your money the way you would: she knows when to buy the better seat without asking and when a purchase needs your eyes first.

After a year, your own family cannot quite reconstruct how things worked before her — and neither can you.

Interview questions worth asking

  1. 01

    Walk me through how you planned the most complicated trip of your last role — what broke, and what had you already planned for?

  2. 02

    How do you decide what reaches your principal and what does not? Give me a real example of each.

  3. 03

    Tell me about a time you made the wrong call on your principal's behalf. How did you handle it?

  4. 04

    What do your preference files look like? What would a stranger covering your desk for a week actually find?

  5. 05

    Why did each of your last positions end, and what would those principals say about you unprompted?

Questions

Hiring a personal assistant, answered.

How is a personal assistant different from an executive assistant?
An executive assistant supports a professional role inside a company — the calendar, meetings, and communications of an executive at work. A personal assistant supports a life: home, family, travel, purchasing, and personal affairs. Many principals need both, and some hire a hybrid. If most of the work happens outside an office, you are looking for a PA — and the discretion requirements are higher, not lower.
How is this different from a private chief of staff?
Scope and altitude. A personal assistant executes — expertly, proactively, but within a life the principal still directs. A private chief of staff directs on the principal's behalf: managing staff and vendors, owning budgets and projects, making decisions across households. If you need superb execution, hire a PA. If you need someone to run the operation so you only touch decisions that require you, that is a chief of staff.
Should the role be in person, remote, or hybrid?
The work answers the question. Wardrobe, errands, household liaison, and event support require presence; calendar, travel, and correspondence do not. Most private PA roles land hybrid — anchored in your city with regular in-person days. Fully remote arrangements suit principals whose needs are administrative, but they narrow what you can delegate. Decide based on the tasks you actually want off your plate, not the arrangement that sounds modern.
How do you vet for discretion?
Carefully, and mostly by listening. We interview for how candidates talk about former principals — the ones who volunteer colorful details fail the test, however impressive the households. We check references directly with prior employers, verify the reasons each role ended, and run thorough background screening. Confidentiality agreements matter, but they are the floor. The instinct not to trade in your life is what we are actually hiring for.

Begin

Looking for a personal 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.