Licensed Insurance Agent - Chicago North
Posted Sep 15, 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 your sales results as a licensed agent. What did you sell, and how did you track your numbers?
What they are checking: Whether they have a real, measurable track record and understand their own sales activity.
This role involves frequent home visits to collect premiums and sell policies. How do you feel about that kind of field schedule?
What they are checking: Whether they truly want in-home field work, since it's very different from phone or office-based insurance sales.
The role pays uncapped commissions. How do you keep chasing commission from pushing you into sales that aren't right for the customer?
What they are checking: Whether they have the integrity to turn down a bad sale even when it would pay them more.
Tell me about a time you turned an unhappy customer into a loyal one.
What they are checking: Whether they can recover trust after a problem, which keeps a book of business from shrinking.
What would you do
You'd be assigned an established book of business. What would you do in your first month with those existing customers?
What they are checking: Whether they would protect and build on the existing book first, rather than chasing only new sales.
A long-time customer has missed two premium payments. How do you handle the visit?
What they are checking: Whether they can protect the policy and the relationship with empathy, without pushing someone into hardship.
How do you find new customers along a route when you're already busy serving existing ones?
What they are checking: Whether they know how to generate referrals and leads from the people they already serve.
About the work
How do you explain the difference between term and whole life insurance to a family on a tight budget?
What they are checking: Whether they know their products and can match them honestly to a modest-income family's real needs.
What's an example of a suitability or compliance rule you follow when selling life insurance?
What they are checking: Whether they understand regulatory duties like suitability and replacement rules, which protect customers and their license.
How do you keep accurate records of collections and policy changes when you're in the field all day?
What they are checking: Whether they are organized with money and paperwork, since mistakes in collections are a serious problem.
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Practice this out loudThe full job description
As published by Kemper.