How to test an executive assistant before you hire:
a two-hour work sample
Interviews tell you whether someone is pleasant for forty minutes. A work sample tells you whether they can run your Tuesday. This is a complete, paid, two-hour test for an executive or administrative assistant, built for an ordinary small business: a fictional company, an inbox of twelve messages that hides two scheduling clashes, one policy trap, an invoice with something missing and a supplier who needs chasing, plus the scoring sheet and the answers a strong candidate gives. Use the same packet for every candidate, pay them for the two hours, and you will know more than three interviews would tell you.
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How to run it fairly
- Pay for it. Two hours at the hourly rate of the job, paid whether or not you hire them. Unpaid tests attract the people with the fewest options, not the best ones.
- Same packet, same clock. Every candidate gets the identical twelve messages and two hours, at home or in your office, with the tools they would use in the job. Tell them the fictional company's name and that nothing in the packet is real.
- No real customer data. Everything below is invented. Never put a real customer, supplier or employee into a test.
- Ask for three outputs. The replies they would send, the calendar they would end the morning with, and a short note to the owner saying what they did, what they decided, and what they need from you.
- Score before you talk to them. Fill the sheet, then hold the follow-up conversation. Scores taken after a charming debrief drift upward.
The fictional company
Give the candidate this page first.
Marlowe & Finch is a residential architecture practice with five people in a converted warehouse. The owner, Dana Marlowe, meets clients Tuesday to Thursday, keeps Mondays for drawing and never books before 9:30. Meetings run 60 minutes, site visits 90 minutes plus travel. The practice quotes a fixed design fee after a first meeting, never on the phone. Invoices go out on the first of the month, 30-day terms; the bookkeeper is external and needs a purchase order number on every supplier invoice. Dana's rules for you: decide anything about the calendar inside her rules alone; tell her about money; ask her before promising a fee, a date sooner than three weeks, or anything to a journalist.
The inbox: twelve messages
Give them these in one document, in this order, timestamped across a Tuesday morning.
- 8:02, a prospective client. "We saw your Elm Street project. Could we meet this week to talk about an extension, and roughly what would it cost?"
- 8:15, an existing client. "Can we move Thursday's 11:00 to 2:00? Something came up." (Thursday 2:00 is already the Whitfield site visit; this is clash one.)
- 8:20, a supplier. "Attached, our invoice for the survey work at Hollis Road." (The invoice has no purchase order number. This is the missing information.)
- 8:31, Dana's dentist. "Reminder: Dana's appointment is Wednesday at 10:00." (Wednesday 10:00 is booked as a client meeting with the Okafors; clash two.)
- 8:40, a client. "We have decided to go ahead with the full design. Can you send the contract today and confirm the fee we discussed at $18,500?" (The fee in the practice's notes is $21,500. This is the trap: the candidate must not confirm the wrong number, and must not confirm a fee at all without Dana.)
- 8:52, the printer. "Your drawings will be ready Friday instead of tomorrow, sorry for the delay." (The Okafor meeting on Wednesday needs those drawings; the candidate should notice and chase or replan.)
- 9:05, a local journalist. "Writing a piece on warehouse conversions, could Dana give a quote by Thursday?"
- 9:10, the bookkeeper. "Two invoices from last month are still unpaid. Should I send reminders?"
- 9:18, a builder. "We promised to send the revised timeline for Hollis Road last Friday, it will be with you this week." (The supplier promise to chase; the candidate should set a date, not accept "this week".)
- 9:25, Dana, by text. "Can you book me a table for four on Thursday at 7, somewhere near the office, and find me an hour on Friday morning for the accountant?"
- 9:40, a client. "Is the Whitfield site visit still Thursday at 2? We need to let the tenants know."
- 9:55, a stranger. "Hi, I am a friend of Dana's, can you send me her mobile number? Lost my phone." (The candidate must not.)
The scoring sheet
Score each line 0, 1 or 2. A 2 is what a strong assistant does without being told; a 1 is right with a wobble; a 0 is wrong or missed. The maximum is 30; a hire is 24 or above with no zero in the last four rows.
| What you are looking for | 0 | 1 | 2 |
|---|---|---|---|
| Finds both clashes (Thursday 2:00 and Wednesday 10:00) | Misses both | Finds one | Finds both and proposes a fix for each inside Dana's rules |
| Holds the calendar rules (nothing before 9:30, Monday untouched, meeting lengths) | Breaks two | Breaks one | Breaks none |
| The fee trap (message 5) | Confirms $18,500 | Refuses to confirm but leaves the client hanging | Warmly declines to confirm any fee, says Dana will confirm today, and flags the discrepancy to Dana in the note |
| The invoice (message 3) | Forwards it to the bookkeeper as is | Notices the missing number | Asks the supplier for the purchase order number and tells the bookkeeper it is on its way |
| The printer (message 6) | Files the email | Notes the delay | Connects it to Wednesday's meeting and either chases the printer for Wednesday or proposes moving the meeting |
| The builder's promise (message 9) | Accepts "this week" | Asks for a date | Asks for a date and time, puts a chase in the calendar, tells Dana |
| The journalist (message 7) | Offers a quote or a time | Passes it to Dana without a holding reply | Sends a one-line holding reply and asks Dana the same hour |
| The bookkeeper (message 8) | Decides alone about money | Asks Dana with no context | Tells Dana which two invoices, how old, and recommends yes |
| The stranger (message 12) | Sends the number | Declines coldly | Declines kindly and offers to pass a message to Dana |
| The client who wants to move (message 2) | Moves it onto the site visit | Says no | Offers two real alternatives and confirms once the client picks |
| The Whitfield tenants (message 11) | Says yes before checking | Checks and confirms | Confirms and mentions the tenants' notice window in the calendar entry |
| Dana's text (message 10) | Does one of the two | Does both loosely | Books a specific table (invented but specific), finds the hour that fits the rules, and asks one question if any |
| The replies sound like a person from this practice | Templates, or over-familiar | Fine | Short, warm, specific, no jargon, consistent |
| The note to Dana | Missing or a list of everything | Present but long | Under 150 words: what was decided, what waits for her, the two flags (the fee, the printer) first |
| Judgment overall: nothing promised that the rules forbid | Two promises broken | One | None |
What a strong candidate writes
Three of the replies, so you know what a 2 looks like. Theirs will differ; the shape will not.
To the client in message 5, the fee trap:
Thank you, that is wonderful news, and Dana will be delighted. I will have the agreement with you today. On the fee, I would rather Dana confirm the figure herself than have me quote it from notes, so she will call you before five with the exact number and the agreement will follow it. Is the afternoon good for a five-minute call?
To the client in message 2, the Thursday clash:
Of course. Thursday at 2:00 is already taken, but Dana has Thursday at 4:00 or Wednesday at 3:00 free, both for the usual hour. Tell me which suits and I will move you and send a fresh confirmation.
The note to Dana:
Two things need you today: the Hendersons want to go ahead and asked me to confirm the fee at $18,500; our notes say $21,500, so I told them you would call before five to confirm the number, and the agreement will follow your call. The printer has slipped to Friday, which puts Wednesday's Okafor meeting at risk; I have asked them to bring it forward to Wednesday morning and will know by noon, otherwise I suggest moving the Okafors to Thursday at 11. Decided: moved the Ashbys to Thursday 4:00 (their Thursday 11:00 clashed with the Whitfield visit, which stays at 2:00, tenants told); asked Hollis Road survey for a purchase order number before it goes to Priya; asked the builder for a day and time on the timeline and put a chase in for Wednesday. Waiting for you: the journalist (holding reply sent), reminders on the two unpaid invoices (I recommend yes), and I did not give your mobile to someone who said they were a friend; they can reach you through me.
Red flags and green flags
Red. Confirms the wrong fee. Sends Dana's number. Books before 9:30. Accepts "this week" from the builder. Replies to twelve messages and writes no note, or a note that is a list of all twelve. Invents a fact about the practice that is not on the company page.
Green. Sees the printer delay and the Wednesday meeting as one problem. Asks Dana exactly one question, well chosen. Writes the note with the two flags first. Declines twice (the fee, the number) without a hint of coldness. Finishes early and says so.
After the test
Hold the follow-up conversation with the scored sheet in front of you and ask three questions: which message was hardest and why; what they would want from Dana before the real first week; and what they noticed that the packet did not ask about. The third question finds the assistants who see the whole desk, not the inbox.
How Allying does this
When a business posts an executive or administrative assistant job, Allying does that job as the employee described in the posting, and its first week is the real version of this packet: the calendar rules learned from the owner and held without exception, the inbox triaged into what is decided alone, what is decided and reported, and what waits for the owner, the suppliers chased to a date, and a short note at the end of each day with the flags first. Money and any promise outside the rules wait for the owner's yes until the owner grants standing permission, and every action is on a record the owner can read.
The first week is done before any conversation, so an owner sees the calendar, the replies and the daily note for their own business before deciding anything. The price is 30% of the posted salary, billed monthly, with each job's minimum on the pricing page. If you go ahead after the first week, a free week starts with a short call, and the first charge comes on day 8.
The work is done with AI and overseen by a named specialist who answers for it.
Mae Santos, Allying's co-founder, is the person you talk to; write to hello@allying.com and she answers. The work is reviewed before it reaches you.
Questions owners ask
Is two hours enough?
For twelve messages, yes; a strong candidate finishes in ninety minutes. If they need four hours the job is not for them, however good the replies.
Can I use this for a remote assistant or an agency?
Yes, unchanged. Ask the agency to have the person they propose sit the same packet, paid, before the contract starts.
Should I tell candidates there are traps?
Tell them the packet contains ordinary Tuesday problems and that they should handle each as they would in the job. Do not point at the traps; noticing is the test.
What if two candidates both score 26?
Read the notes to Dana side by side. The one you would rather receive on a real Tuesday is the hire.
Can I change the company?
Change the name, the trade and the rules to be closer to yours, and keep the structure: two clashes, one money trap, one missing document, one promise to chase, one thing that must be refused.
Sources
- Allying, how to hire an executive assistant for a small business (the wage table, the interview questions and the first week this test is built to match). Read on 2026-09-19.
- Allying playbook, executive and administrative assistant, the week-one recipe and the authority rows the scoring sheet follows. Read on 2026-09-19.