Underwriting Manager - Middle Market
Posted Aug 27, 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 a time you coached an underwriter whose files kept getting sent back.
What they are checking: Whether they develop people through specific feedback instead of just fixing the work themselves.
Tell me about a time you worked with other teams to win a new account.
What they are checking: Whether they collaborate across functions and present well in new-business pursuits.
Tell me about a time you had to have a hard performance conversation. What happened afterward?
What they are checking: Whether they address performance directly and fairly instead of avoiding it.
What would you do
How do you balance growth and profitability when an agency is pushing hard on a large account with mixed loss history?
What they are checking: Whether they can protect underwriting discipline while keeping an important agency relationship healthy.
You think a process is slowing the team down. How would you change it and know whether the change worked?
What they are checking: Whether they improve processes and then check results, which the posting asks them to monitor.
An insured calls you directly, angry about a declined renewal. How do you handle it?
What they are checking: Whether they can handle difficult inquiries personally while backing a sound decision.
This role is in our Madison regional office on a hybrid model. How do you lead a team when people aren't always in the office together?
What they are checking: Whether they can keep a hybrid team connected and consistent in how they underwrite.
About the work
Walk me through how you'd review a complex middle market account that's beyond your underwriters' authority.
What they are checking: Whether they have the technical depth to interpret guidelines on the hardest files the team sees.
What metrics do you watch to know whether your team's book is healthy?
What they are checking: Whether they manage with real measures like loss ratio, retention, hit ratio and rate, not gut feel.
What lines of coverage in middle market do you know best, and where are you less sure?
What they are checking: Whether they have an honest view of their technical range across all middle market lines.
How do you design underwriting training for a mix of new and experienced underwriters?
What they are checking: Whether they can build training that meets people at different levels rather than one-size-fits-all.
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Practice this out loudThe full job description
As published by Sentry Insurance.