Hiring an executive assistant is not really a hiring problem. It is a trust problem.
That distinction changes how you should run the process.
This person will see your calendar, your inbox and conversations you have not had with your own leadership team yet. So the usual screening questions matter less than they do elsewhere. What matters is judgment, discretion and whether what they told you is true.
Most interview processes for this role test none of those things.
Define the job before you write the posting
Hiring an executive assistant starts with a definition problem, not a sourcing one.
Executive assistant means very different things across companies. In one it is calendar and travel. In another it is chasing decisions across departments, handling board material and speaking on your behalf.
So write down what the first 90 days actually involve. Be specific. Which decisions can they make alone? Which inboxes do they own? Who do they chase when you are unavailable?
That list becomes your posting and your screening criteria. Without it, you will interview for general competence and hire whoever interviewed best.
The same principle applies to any role you hire for, which we covered in our piece on hiring beneath the surface.
Interview questions that reveal judgment
Standard questions produce standard answers. Everyone claims to be organised. So ask about situations instead, and pay attention to what the answer reveals about how they think.
- Tell me about a complex schedule you managed. What broke, and what did you do about it?
- Describe a time you had information your manager’s team did not. How did you handle it?
- You have 3 urgent requests from 3 people who all outrank you. Walk me through your next hour.
- Tell me about a project you ran start to finish. Where did you need permission, and where did you decide alone?
- Describe a difficult person you worked with. What did you change about your approach?
- When have you pushed back on your manager, and what happened?
That last question is the one most worth asking. An assistant who has never disagreed with an executive will not protect your time, and protecting your time is much of the job.
What to listen for
Strong candidates describe their reasoning, not just the outcome. They explain the trade off they made and why.
Weak answers stay generic. Watch for people who describe what they would do in theory rather than what they actually did.
Pay attention to tone too. This person represents you in writing and on calls, so how they speak in an interview is a reasonable preview.
Why verification matters more in this role
For most roles, checking a resume is good practice. When hiring an executive assistant, it is the core of the decision.
Think about what you are handing over. Confidential documents, access to your accounts, and knowledge of things not yet public. So the gap between what a candidate claims and what is true carries a different weight here than it does in a warehouse hire.
And this is exactly where hiring processes get rushed. Reference checks take days, past employers respond slowly, and the temptation is to skip them because the candidate was impressive in conversation.
Workwolf® handles that part as a standalone service. Our verification checks cover employment records, academic credentials, certifications, references and criminal record checks. So you get confirmed facts rather than a promise you have to trust.
Adding a behavioural read
Verification tells you what is true. It does not tell you how someone works under pressure, which is the other half of this decision.
That is what Packfinder measures. We built it with Self Management Group, who report that more than 30 million people have completed the assessment. That volume is what lets it compare a candidate against real patterns rather than a small sample.
For a single hire it will not replace your judgment. Still, it gives you a second read on discretion and independence before you hand over your calendar.
The mistake most people make
Almost every posting for this role leads with organisation and software skills. Both are easy to teach.
Judgment is not. Neither is the instinct to know which of your 40 daily requests actually matters, or when to say no on your behalf.
So weight your process accordingly. Screen for tools if you must, but decide on judgment.
Where to start
Hiring an executive assistant well comes down to preparation. So write the 90 day list first. If you cannot describe what this person will own, you are not ready to interview.
Then pick 4 of the questions above and ask every candidate the same 4. Comparing answers across people tells you far more than a free flowing conversation with each one.
And verify before you offer, not after. Talk to our team about running verification on your shortlist.
