AI executive assistant or a real one? A cost and task comparison

Sort the week before you compare prices

Here is what I would do first. Open last week's calendar and your sent folder, and tag every chunk of time with one of three labels.

Yours: the advice, the hard call, the meeting a client pays for. Person: phone calls, travel, events, chasing someone who ignores email, anything physical. Nobody: sorting email, routine replies, finding a meeting time, writing up a call, reminding you what you promised.

If the person pile is the big one, hire. If the nobody pile is the big one, set up the AI first and look at what is left after a month.

What each option costs

• Executive assistant, salaried. Median pay for executive assistants (BLS occupation 43-6011) was $76,590 a year in May 2025 (BLS). Payroll taxes, benefits and equipment come on top of that figure.
• Part-time assistant, 10 hours a week. $76,590 divided by a 2,080-hour work year is about $37 an hour. Ten hours a week at that rate is roughly $1,600 a month in wages. That is arithmetic on the BLS median, so real quotes in your area will differ.
• Claude Pro. $20 a month billed monthly, or $17 a month billed yearly (Claude pricing). One person.
• Claude Team. From $25 a seat a month billed monthly, with a 2-seat minimum. Built for a practice with staff.
• Setup. Your own time, spent connecting tools and writing instructions. Or my workshop, two working sessions on your own accounts, $599.

Who does which task

• Inbox sorting and routine replies: AI. It drafts, you approve. Anthropic's help center says sending, replying and forwarding through the Gmail connector ask for your approval by default (help center). Anthropic's Gmail docs call the connector read-only, so check what yours can do.
• Finding a time for four people: AI, through Google Calendar. A person if the four people need phoning.
• The recap after a call: AI, from your notes or transcript.
• Keeping the CRM current: AI, where your CRM connects to Claude. A person if it does not.
• Answering the phone, booking travel, running an event: Person.
• Saying no to people on your behalf: Person.
• The advice itself: You.

When a person is the right call

The AI cannot take a call, travel or show up anywhere. If your phone pile is bigger than your email pile, a person earns their cost. Same if you travel often, run events, or need someone physically in the office.

If you want a gatekeeper with judgment, someone who can read a client's mood and decide whether to interrupt you, that is a person too. Claude does not interrupt you. It acts when you ask, by your written rules.

And if the budget is there and you never want to think about setup, hiring is a fair choice. A new hire has to learn your clients too, and so does the AI, in writing.

Running both

If both piles are big, split the work by where it lives. Everything in email, the calendar and the CRM goes to the AI, set up with your rules. The phone, travel and anything in person goes to a part-time person.

Write down the split on day one. Who owns follow-ups. Who books meetings. Who updates the CRM.

If email is the biggest piece, start with an AI email assistant that writes like you. If you want to build the instructions yourself, start with Claude skills.

Questions