Commercial Real Estate Banker, AVP / VP
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 a CRE deal you closed, from first conversation to funding.
What they are checking: Their real experience leading deals and working with credit to get them approved.
Tell me about a deal you walked away from. Why?
What they are checking: Their discipline in saying no to deals that do not fit the bank's risk appetite.
How do you manage the relationships in your existing portfolio while chasing new business?
What they are checking: Their ability to balance retention and growth, since the role manages existing clients too.
What would you do
How would you build a pipeline of commercial real estate deals in Chicago?
What they are checking: Their business development plan and existing relationships with developers, brokers and investors.
A strong client wants terms that credit won't approve. How do you handle it?
What they are checking: Whether they can balance client relationships with sound credit and find workable structures.
One of your borrowers is struggling to make payments. What do you do?
What they are checking: Their willingness to act early and work with the borrower and credit team on a solution.
Wintrust emphasizes relationship-focused community banking. How do you compete against larger banks for deals?
What they are checking: Whether they can win on service, speed and relationships rather than only on price.
About the work
What makes a construction loan riskier than a loan on a stabilized property?
What they are checking: Their understanding of construction risks such as cost overruns, timing and lease-up.
How do you size a loan using debt yield, DSCR and loan-to-value?
What they are checking: Their technical command of CRE loan sizing.
How do you bring deposits and treasury services into a real estate relationship?
What they are checking: Whether they think about the full banking relationship, not just loans.
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Practice this out loudThe full job description
As published by Wintrust.