Interview questions · Sales
8 questions for interviewing a Insurance Agent — each with what a strong answer sounds like and the red flag to catch. Written for founders interviewing without a recruiter.
Listen for: A specific deal, a named reason rooted in discovery or qualification, and what they changed since.
Red flag: Blames pricing, product, or the buyer every time — no personal lever identified.
Listen for: A real disqualification story with criteria — budget, authority, timing — applied early.
Red flag: Never walks away; treats every lead as workable. That burns small-team pipeline fast.
Listen for: Questions before pitching — good sellers diagnose first. Clear value framing over feature lists.
Red flag: Launches straight into a feature monologue without asking anything about "your" needs.
Listen for: Numbers offered without hesitation, including the bad quarters, with context for each.
Red flag: Vague percentages, "we" numbers, or visible discomfort with specifics.
Listen for: Exit criteria per stage, next-step discipline, and examples of downgrading their own deals.
Red flag: Pipeline hygiene framed as something managers impose rather than a personal habit.
Listen for: Learning before changing, early small wins, and questions about how you’d measure them.
Red flag: Grand transformation plans before understanding the context, or no ambition at all.
Listen for: Lived-experience insight that only someone who’s done the job would know.
Red flag: Generic answers that could come from reading the job description.
Listen for: A real weakness stated plainly, plus the compensating system they’ve built.
Red flag: A humblebrag ("I care too much"), or claiming the manager would say nothing.
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