Senior Administrative Assistant. Real Assets (Chicago)
Posted Sep 23, 2026 · We last checked this listing on Oct 6, 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
Tell me about the most complex calendar you've managed. How many people were you supporting, and how did you keep it from falling apart?
What they are checking: Whether they have handled senior-level calendar load before or are stepping up from a lighter support role.
Tell me about a time you made a mistake on someone's schedule. What happened and what did you change afterward?
What they are checking: Whether they own errors honestly and build a habit that prevents the same slip from happening again.
How do you organize your day when you're juggling scheduling, travel, expenses and a pile of ad hoc requests all at once?
What they are checking: Whether they have a real method for multitasking rather than just reacting to whoever asks loudest.
Describe a time you had to push back on or redirect a senior person politely. How did you word it?
What they are checking: Whether they have the confidence and tact to manage up, which senior executives quietly expect from a strong assistant.
What would you do
Two senior partners in Real Assets both want the same open hour, and each says theirs is urgent. What do you do?
What they are checking: Whether they can weigh competing priorities calmly and loop in the right person instead of guessing.
An executive's flight to a site visit gets canceled late at night and they have a meeting at 9 a.m. the next day. Walk me through what you do.
What they are checking: Whether they can solve travel problems fast and think ahead about who else needs to know about the change.
In an asset manager you see confidential deal names, investor details and compensation. How do you handle that kind of information day to day?
What they are checking: Whether they understand discretion in a public investment firm and know what never gets mentioned outside the room.
About the work
Walk me through how you put together board materials. Where do errors usually creep in, and how do you catch them?
What they are checking: Whether they treat board books as high-stakes documents with version control and a final check, not just formatting.
How do you handle expense reporting for executives who travel a lot and lose receipts?
What they are checking: Whether they have a system that keeps expenses accurate and on time without nagging busy people constantly.
What tools do you use most, like Outlook, Concur, Excel or PowerPoint, and which one are you strongest in?
What they are checking: Whether their software skills match the daily work so they can be productive without heavy training.
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Practice this out loudThe full job description
As published by Blue Owl Capital.