The short answer
Decide what this person will own on your behalf: your calendar, your inbox, your decisions, or all three. Then write down what they can decide without asking you, and hire the executive assistant whose working style fits how you work, not just the one with the longest resume or the best interview. A poor fit lands on one person, you, and arrives as time spent re-explaining, re-checking, or doing it yourself.
Why this hire is hard right now
The numbers say a steady, small market. Job Bank rates the Toronto-region outlook for executive assistants "moderate" for 2025 to 2027: a few new positions, several openings from retirements, and a moderate number of unemployed workers with recent experience. About 9,340 people hold these jobs in the region, and finance, insurance, and real estate employ 28% of them, professional, scientific and technical services 14%. In the US, BLS projects flat employment for executive secretaries and executive administrative assistants through 2035: 489,300 jobs in 2025, 100 fewer by 2035.
The story under the numbers is AI. Bloomberg reported in May 2026, citing people familiar with the matter, that PwC's US arm laid off about 600 executive assistants, recruiters, and other support staff in February. The article describes firms cutting support roles to make room for AI. If scheduling is what tools take, the job that remains is judgment on your behalf, which depends more on one working relationship than any other role. Know how you work, write it down, and hire someone whose style matches or complements it.
What an executive assistant does
BLS describes executive assistants as giving high-level support to an office and its top executives: reviewing incoming documents, conducting research, and preparing reports, with some supervising clerical staff. How far that goes is your decision. Three levels cover most jobs:
| Level | What it looks like | What you need to have decided |
|---|---|---|
| Runs your calendar | Schedules, books travel, arranges meetings | Which meetings can move, and whose time outranks whose |
| Speaks for you | Drafts and sends messages, screens your inbox and calls | Which messages go out without your approval |
| Decides for you | Sets your priorities, reviews documents, handles confidential matters | What they can say no to, and what they must bring to you |
The third row is the one people rarely write down.
The most useful thing you can give an executive assistant is a list of what they can decide without asking.
Working style: write it down first
Neither answer in the table is wrong. The trouble starts when an assistant and an executive hold opposite ones.
| Moment | Write down, for how you work | What a mismatch looks like |
|---|---|---|
| Something goes wrong | A flight is cancelled, or a message went out you did not want sent: do you want to hear at once, or hear it solved? | A double-booked call is quietly fixed by moving the wrong meeting, and you find out in the room. |
| Instructions conflict | Your instruction clashes with a colleague's, or with what you said last week: who wins, and should the assistant raise it? | The newest instruction wins, even when it quietly reverses an earlier one. |
| Feedback | Do you want to be told when you are wrong, such as double-booking yourself? Will you say when they are? | Neither side raises it, and the assistant becomes a messenger instead of a partner. |
| Speed against quality | Which messages go out in your name fast, and which does the assistant draft for you to approve? | Everything waits for your approval and you become the bottleneck, or nothing does and a message goes out you would not have sent. |
Where your answers are "it depends," write down what it depends on. That is the part a candidate cannot guess.
What a bad hire costs
The most transparent estimate puts the cost of replacing an employee at about a fifth of salary, and it is probably low. A 2012 review by the Center for American Progress found a median of 21% of annual salary across most jobs. Only 2 of its 11 papers counted indirect costs such as lost productivity. The data are historical and American, so read them as an order of magnitude. For an executive, the larger bill is time and confidence: hours spent re-explaining, and a calendar you stop trusting.
What fit research does and doesn't show
A 2005 meta-analysis of 172 studies found that fit with a supervisor tracked how people felt about the supervisor (corrected correlation .46) and the job (.44), but much less performance (.18) or tenure (.09). A 2022 summary of research on leader-member exchange, the quality of the relationship between someone and their boss, found it moderately linked to performance, satisfaction, and commitment, and to intentions to leave, but not to whether people actually leave. The reading: the relationship shapes how the work goes more than whether the person stays. For an assistant who works for one person, the relationship is most of the work.
How to screen for fit
Ask every candidate the same questions and score the answers against what you wrote down. A 2022 re-analysis of hiring research (Sackett and colleagues) ranked structured interviews first, with a validity of .42, ahead of work samples at .33, as summarized by SIOP. The figures cover job performance across occupations, not executive assistants specifically.
Questions that surface working style
Ask about a real past situation, then keep asking "what did you do next?" until you hear actions, not intentions.
- Something went wrong: "Tell me about a mistake made in an executive's name: a message, a booking, a commitment. What did you do first, and who did you tell?"
- Instructions conflicted: "An executive's instruction clashed with what another leader wanted, or with something they said earlier. What did you do?"
- Feedback: "Tell me about a time you disagreed with an executive's decision. How and when did you say so, and what happened?"
- Speed against quality: "What did you send for approval, and what did you handle alone? How did you learn where the line was?"
A 30-minute work sample
Hand over a mock week: a calendar with three conflicts, five emails to answer in your name, one of them confidential and one from someone you would normally decline, and a missing fact such as who is travelling. Ask for a one-page note on what they would do, what they would decide, and what they would ask you. Watch for:
- Asks what they may decide: strongest.
- Decides, then tells you what they decided: good.
- Decides silently: a risk, whatever else the note shows.
References
Ask a former executive: "What did this person need from you to do their best work?" Then spend an hour with each finalist on a real week's calendar.
Canada and the US
| Ontario | United States | |
|---|---|---|
| Usual title | Executive assistant (NOC 12100). | Executive secretary or executive administrative assistant. |
| Size | About 9,340 in the Toronto region (Job Bank). | 489,300 jobs in 2025 (BLS). |
| Median pay | C$35.93 an hour, range C$26.14 to C$50.00 (Job Bank, 2023 to 2024 data). Toronto region: C$36.06. | US$76,590 a year (BLS, May 2025). |
| Outlook | "Moderate" for 2025 to 2027, Toronto region. | Flat employment, 2025 to 2035. |
FAQ
What does an executive assistant do?
BLS says they give high-level support to an office and top executives: reviewing incoming documents, conducting research, and preparing reports. In practice, how much they decide for you is the real definition of the job.
What is the difference between an executive assistant and an office administrator?
An executive assistant works for a leader or a few; an office administrator runs the office for many. BLS's May 2025 median pay is US$76,590 for executive roles and US$47,540 for the group excluding legal, medical, and executive.
How much does an executive assistant earn in Ontario?
Job Bank's Ontario median is C$35.93 an hour, with a range of C$26.14 to C$50.00 (2023 to 2024 data). The Toronto-region median is C$36.06.
What should I ask in an executive assistant interview?
Ask about real past situations: a mistake made in an executive's name, conflicting instructions, disagreeing with a decision, and where the approval line sat. Use the same questions for every candidate and add the mock-week work sample.
Will AI replace executive assistants?
Nobody knows yet. BLS projects flat employment for executive roles through 2035, and Bloomberg reported AI-related cuts at large firms in 2026. Hire for the part tools do not do: judgment about what to decide and what to bring to you.
Sources
All pages opened October 27, 2026.
- U.S. Bureau of Labor Statistics, Occupational Outlook Handbook: Secretaries and Administrative Assistants, executive row (last modified August 27, 2026)
- Job Bank, Government of Canada: Executive assistants (NOC 12100): outlook, Toronto region (2025 to 2027; outlook updated December 10, 2025)
- Job Bank, Government of Canada: Executive Assistant (NOC 12100): wages in Ontario, with a Toronto row (Labour Force Survey, 2023 to 2024; updated November 19, 2025)
- Bloomberg Government (James Booth), May 21, 2026: Executive Assistants Making $100,000 a Year Lose Jobs to AI. Paywalled; I read the visible portion only.
- Quality Improvement Center for Workforce Development (Stepanek and Paul), June 22, 2022: Umbrella Summary: Leader-Member Exchange
- Center for American Progress, Boushey and Glynn, November 16, 2012: There Are Significant Business Costs to Replacing Employees
- Kristof-Brown, Zimmerman and Johnson (2005), Personnel Psychology 58(2), 281 to 342: Consequences of Individuals' Fit at Work. Person-supervisor figures from Table 4.
- Sackett, Zhang, Berry and Lievens (2022), Journal of Applied Psychology 107(11), 2040 to 2068, as summarized by SIOP's TIP