Interview questions · Customer
8 questions for interviewing a Technical Support Engineer — each with what a strong answer sounds like and the red flag to catch. Written for founders interviewing without a recruiter.
Listen for: De-escalation steps, listening before solving, and a resolution the customer accepted.
Red flag: The story is about winning the argument rather than keeping the customer.
Listen for: Clear personal thresholds — data loss, billing, legal — and fast ownership below them.
Red flag: Escalates everything (no ownership) or nothing (no judgment).
Listen for: Honesty early, an alternative offered, and the reason explained in the customer’s terms.
Red flag: Soft-yes answers that defer the no — that’s how churn surprises happen.
Listen for: Usage drops, champion departure, support tone shifts — and a playbook for each.
Red flag: Only reacts to the cancellation email.
Listen for: Pattern recognition across tickets turned into a fix upstream — docs, product, onboarding.
Red flag: Happily answers the same question 200 times without ever flagging it.
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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