2027 Starr Summer Intern - Chicago
Posted Sep 1, 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
What do you know about commercial property and casualty insurance, and what made you interested in it?
What they are checking: Whether they did basic homework and have a real reason for choosing this industry over others.
Tell me about a time you had to learn something unfamiliar quickly for a class, job or project.
What they are checking: How fast they get up to speed, which matters in a ten-week program with a lot of new material.
The program ends with a chance to present. Tell me about a presentation you gave and how you prepared for it.
What they are checking: Comfort speaking to an audience and whether they prepare deliberately, since presentation skills are a program objective.
Tell me about a group project where someone wasn't pulling their weight. What did you do?
What they are checking: How they handle team friction, since interns work closely with a cohort and with full-time staff.
What would you want to have learned by the end of ten weeks for the summer to feel like a success?
What they are checking: Whether they set goals for themselves and think about the internship as a step toward a career here.
What would you do
Interns may land in Claims, Underwriting, Audit, IT, Marketing or HR. Which area are you most drawn to, and how would you handle being placed somewhere else?
What they are checking: Flexibility and genuine curiosity, since department needs drive placement in a program like this.
Your mentor gives you a task with little direction and then gets pulled into meetings all day. What do you do?
What they are checking: Initiative and judgment about when to push ahead versus when to wait for guidance.
Networking is part of the program. How would you approach meeting people in other departments over the summer?
What they are checking: Whether they will use the program actively to explore full-time paths rather than staying in their own lane.
About the work
In plain words, how would you explain to a friend what an underwriter does versus what a claims adjuster does?
What they are checking: Basic grasp of the core insurance functions and the ability to explain them simply.
How comfortable are you with Excel? Tell me about something you built or analyzed with it.
What they are checking: Practical spreadsheet skill, which almost every department here relies on for daily work.
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Practice this out loudThe full job description
As published by Starr Insurance.