Executive Assistant
Posted Aug 5, 2026 · We last checked this listing on Oct 4, 2026
Likely interview questions for this role
Written from this job description, not a generic list. Each one notes what the interviewer is really checking.
About your past
You would coordinate travel including flights, hotels and car services, and assist with expense reports. Tell me about a trip that fell apart and what you did.
What they are checking: Whether they stay calm and resourceful when travel plans fall apart, because an executive stranded mid-trip needs fast, practical fixes from their assistant.
The posting asks you to anticipate the needs of leadership by proactively managing complex calendars. What does anticipating actually look like?
What they are checking: Whether they actually plan ahead for leadership's needs rather than reacting to requests, which is what makes an executive assistant truly valuable.
The posting names a high degree of personal integrity to maintain trust across senior leadership. What kind of information would you be trusted with, and how do you protect it?
What they are checking: Whether they can be trusted with sensitive leadership information and keep it protected, because discretion is the foundation the whole role rests on.
Tell me about working for someone demanding. What did you learn about how to support them?
What they are checking: Whether they adapt to how a demanding person works and learn from it, because supporting senior leaders means fitting their style, not yours.
This supports FIRST Insurance Funding, a premium finance business, at $27.00 to $39.50 an hour asking three to five years. What would you want to know about the executives you would support?
What they are checking: That they treat the fit with the principals as the deciding factor.
What would you do
You would manage the daily schedule and travel for a chief executive, a president and a chief operating officer. When their calendars conflict, how do you decide?
What they are checking: Whether they can fairly balance three senior executives' competing demands, since juggling conflicting calendars without picking favorites is the hardest part of this role.
You would create the agenda deck for monthly executive meetings by collecting updates from other executives. How do you get those updates in on time?
What they are checking: Chasing senior people for inputs, which requires tact and persistence.
You would coordinate visits of outside guests and candidates. What makes a visitor's day go well?
What they are checking: Attention to the guest experience as a reflection on the firm.
You would handle personal arrangements for executives as well as business ones. How do you hold a boundary while still being helpful?
What they are checking: A real and delicate part of this job, stated in the duties.
About the work
You would set up and prep materials for company-wide meetings. How do you make sure nothing is missing before the room fills?
What they are checking: Whether they prepare thoroughly and check details before a meeting starts, since gaps become very visible once the whole company is in the room.
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Practice this out loudThe full job description
As published by Wintrust.