This week’s question from our portal “Ask Us Anything” comes Todd
I heard you say something recently about asking better questions to get better responses, and I feel convicted about this area of my life. I realize I’ve gotten lazy with my questions, often defaulting to things like “How are you?” or comments about the weather. I spend most of my time with my wife since we both work from home, and sometimes I literally stare at her thinking “I have no idea what to ask you.” In business contexts, I understand the importance of questions that lead prospects to realize the value of what I’m offering, but how do I improve my question-asking skills in general? How do I move beyond surface-level conversations?
The key to asking better questions is understanding what response you want to elicit. In business, if you want someone to say “I highly value what you’re offering and want that for my business,” you need to craft questions that naturally lead to that conclusion.
Let me give you a specific example from the insurance industry. When a client pushes back on cost, you might ask: “What’s more important to you – the value of properly protecting everything you’ve worked for, or saving money and putting your business at risk? Which matters more?” This question forces them to reveal their value system and think about the real trade-offs they’re making.
You could follow up with: “Of course cost is important – everyone has to manage costs. But we’re not really talking about cost. We’re talking about what happens if something goes wrong and wipes out your business. So you have two costs: one you can pay now to protect yourself, or pennies saved now but potentially a massive cost later. Which is more important to you?”
These questions aren’t manipulative – they’re helping people clarify their own priorities. If they truly value saving money now over protection, that’s their choice, but they’ve made it consciously.
For personal relationships, especially long-term ones like with your husband, focus questions on areas of growth, dreams, reflections, or new perspectives: “What’s something you’ve been thinking about lately that we haven’t discussed?” or “If you could change one thing about your work routine, what would it be?” The goal is to discover new aspects of someone you already know well.
The art of asking better questions comes from genuine curiosity about the other person’s perspective and a desire to go beyond surface exchanges. Practice crafting questions that invite deeper reflection, and you’ll be amazed at how conversations transform.
