Commercial Real Estate Banker II
Posted Jul 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
Walk me through how you'd build a pipeline of commercial real estate prospects in the Chicago market from a standing start.
What they are checking: Whether they have a repeatable prospecting method or just wait for referrals to show up on their desk.
Tell me about a CRE deal you closed that almost fell apart. What saved it?
What they are checking: How they handle late surprises like appraisal gaps or environmental findings without losing the client or the bank's protections.
Tell me about a time credit declined or restructured a deal you believed in. How did you handle it with the client?
What they are checking: Whether they can deliver bad news honestly and keep the relationship without blaming the bank's credit team.
Where do your referrals come from today, and how would you widen that network around Rosemont and Chicago?
What they are checking: Whether they already have ties to brokers, attorneys and developers that can feed new business.
What would you do
Office vacancy is up and your borrower's anchor tenant just gave notice. What do you do in the first week?
What they are checking: Whether they get ahead of a deteriorating credit with the borrower and credit team instead of hoping it resolves.
How do you decide when a prospect isn't a fit for a community bank like Wintrust and should go elsewhere?
What they are checking: Whether they protect the bank's risk appetite and their own time instead of forcing every deal through.
Wintrust wants deposits and treasury services along with the loan. How do you bring that into a real estate conversation?
What they are checking: Whether they treat relationships as full banking relationships rather than one-off loans that bring no deposits.
About the work
A developer brings you a multifamily construction deal. What are the first numbers you look at to decide whether it's worth taking to credit?
What they are checking: Whether they can screen a deal quickly on debt service coverage, loan to value and sponsor strength before wasting anyone's time.
How do you explain the difference between loan to cost and loan to value to a borrower who thinks they should get the higher number?
What they are checking: Whether they understand construction lending math well enough to teach it calmly to a client who wants a different answer.
What do you look for in a sponsor's real estate schedule and global cash flow?
What they are checking: Whether they can spot a sponsor who is overleveraged across other properties even when this one deal looks clean.
How do you stay current on cap rates, rents and construction costs across the property types you lend on?
What they are checking: Whether their market knowledge is current enough to challenge a borrower's pro forma rather than accept it.
Practice this interview out loud.
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Practice this out loudThe full job description
As published by Wintrust.