
Asking Better Questions
Earn the specific answer by understanding the whole picture first.
Three questions, in order. Each one narrows the ground the next one stands on. Resist the urge to jump to your pet theory: earn the narrow question by mapping the landscape first.
Survey the whole picture, no assumptions. "How's the new onboarding process actually going?"
Zero in on where the pain lives. "What's been the hardest part to get right?"
Pin the one root cause. "Is that a training gap, or is the tool itself getting in the way?"
“Honestly, we're not seeing the results we expected.”
“Tell me how it's been going overall. Then, where does it feel like it breaks down most? And when it breaks, is that on our side or in the handoff to your team?”
Elena Ruiz, customer three months in
“We're just not getting the value we thought we would. Something's off.”
Funnel it: one wide question, one that narrows to the theme, one that lands the specific root cause. Do not jump to the narrow question first.
A strong answer: “Walk me through how it's been going since launch. Where does it feel like the value leaks out? And is that a workflow thing on your end, or something the product isn't doing for you?”
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Wide, narrow, specific. Map the landscape before you drill.
This is one lesson from the Asking Better Questions course in the Insight7 app, with a roleplay to rehearse the real conversation.