The Worst Interview Questions and What to Ask Instead
The worst questions are ones that can be answered yes or no, ones that contain their own answer, and ones so broad the guest has to guess what you want. Replace them with questions that ask for a specific instance, because instances produce stories and stories are what people remember.
Some questions are structurally incapable of producing a good answer. It does not matter how interesting the guest is.
"So tell us about your business"
Too broad. The guest has to guess what you want and will default to their networking pitch, which is the least interesting thing they own.
Instead: "What were you doing right before you started this?" Specific, easy, and it starts a story rather than a summary.
Any question answerable with yes or no
"Was it hard getting started?" invites one word. A generous guest will expand anyway, which means they did your job for you.
Instead: "What was the hardest month of the first year?" Same territory, but it requires a specific answer.
Questions with the answer built in
"You must have been really proud when that happened, right?" You have now told them what to feel and the only available answer is agreement.
Instead: "What did that actually feel like?" Leave the emotion for them to name. Sometimes it is not pride, and that is the interesting version.
"What advice would you give?"
This produces platitudes almost every time. Work hard, stay focused, believe in yourself. Nobody has ever been changed by an answer to this question.
Instead: "What would you tell the version of you who was starting out?" Same intent, but it forces a specific person in a specific situation, and the answers get real and occasionally quite raw.
The multi-part question
"So how did you get started, and what was that like, and where do you see it going?" The guest answers the last part and forgets the rest, and you lose two questions.
Ask one thing. Wait. Ask the next thing. This is the easiest fix on this list and the most commonly ignored.
The replacement rule
Almost every bad question improves the same way. Ask for an instance rather than an assessment. "When did that matter most?" beats "how important is that?" every single time.
Questions, answered
What is the worst question to ask in an interview?
Anything that can be answered yes or no, and anything that contains its own answer. Both hand the guest an exit and produce nothing usable.
How do you ask a good open-ended question?
Start with what, how, or when, and ask for a specific instance rather than a general assessment. "When did that matter most" produces a story. "How important is that" produces an adjective.
Why is asking for advice a weak question?
It invites platitudes, because advice is general by nature. Asking what they would tell their earlier self produces the same wisdom attached to a specific person and moment, which is far more usable.
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