Asking Better Questions
How to ask questions that build trust
Make people feel seen, not processed: ask like you care, not like a checklist.
Why it matters
Checklist questions collect data and leave people feeling processed, like a number in your pipeline. Trust questions collect the same data plus the why underneath, and the person walks away feeling understood. One builds a transaction, the other builds a relationship.
How to do it
Before you ask, check: am I asking because I need this answer, or because I want to understand this person? Lead with trust, then confirm the logistics. Same information, warmer door.
Ask about the win
Not "what's your budget," but "what would a real success here look like for you?" You get the number and the motivation behind it.
Ask about the why
Not "what's your timeline," but "what's driving the urgency?" The deadline plus the reason it exists.
Ask about the person
"What made this land on your plate?" Shows you see them, not just the role on the org chart.
Ask about the stakes
"What changes for your team if this actually works?" Invites the feeling under the facts.
What it sounds like
Prospect
“Team's about forty, we're on the old system, hoping to switch by Q3.”
You
“Got it. Setting the logistics aside for a second: what would actually change for your team if this worked the way you're hoping?”
Practise it
Hannah Weiss, prospect on a first call
“Yeah, so that's the size, the stack, and roughly when we want to move. What else do you need?”
Ask one question that shifts this from transactional to relational. Make her feel you're genuinely curious about her, not just qualifying the deal.
A strong answer: “Before we get into the mechanics, I'm curious what a genuine win looks like for you personally here. What would make you glad you took this on?”
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The short version
Lead with curiosity, confirm the logistics after. People open up to someone who clearly wants to understand them.
Practise it every day
This is one lesson from the Asking Better Questions course in the Insight7 app, with a roleplay to rehearse the real conversation.