Financial Assistant
Posted Sep 29, 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
Wintrust Wealth Management serves high net worth individuals, business owners and institutions. What experience do you have supporting financial advisors or wealthy clients?
What they are checking: Whether they understand the service level and discretion that private clients expect.
Tell me about a time you caught an error before it reached a client.
What they are checking: Whether they double-check their work, since mistakes with client money are costly and damage trust.
What does confidentiality mean when working with high net worth clients?
What they are checking: Whether they understand that discretion is essential and goes beyond just following privacy rules.
What would you do
A client calls asking to move money from their account today, but their advisor is in meetings all afternoon. What do you do?
What they are checking: Whether they follow verification and authorization steps rather than acting on a request just to please the client.
You get a call that sounds like a client, but something about the request seems off. How do you handle it?
What they are checking: Whether they can spot possible fraud and verify identity before acting, which protects clients.
How do you manage tasks for more than one advisor when their priorities conflict?
What they are checking: Whether they can prioritize fairly and communicate clearly instead of letting work quietly slip.
About the work
How do you prepare an advisor for a client review meeting?
What they are checking: Whether they know what goes into meeting prep, like account statements, performance and open action items.
What account paperwork have you processed, such as new accounts, transfers or beneficiary changes?
What they are checking: Whether they have handled the core operational forms that keep a wealth practice running.
Are you licensed, such as the SIE or Series 7, or would you be open to earning those licenses?
What they are checking: Whether they have or will get the licenses that often let assistants take more on for advisors.
What tools like Excel or CRM systems have you used to track client information?
What they are checking: Whether they can keep client records organized and up to date in the systems a wealth team relies on.
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Practice this out loudThe full job description
As published by Wintrust.