Your Fear of Asking Deeper Questions is Hurting Your Sales: How Being Authentically Curious Can Help


Asking questions and forming bonds and relationships with your prospects is Sales 101. But how many of us are afraid to go deeper and ask the RIGHT questions to truly empathize with our customers?

A lot, as it turns out.

It’s scary to put yourself out there and risk judgement by asking more personal questions on the first meeting — a lot of sales professionals I have worked with always start out building “rapport” by talking about common interests, but these end up being Bullshit Questions. BSQ’s are those superficial questions everyone asks, talking about sports, the weather, and staying on the top layer of family dynamics in fear of going deeper and offending someone.

I challenge you to go against this feeling and go deeper. Get really curious about your prospects because it’s scientifically proven to actually help you bond faster with your customer. Here’s a summary of everything covered in the video, but watch it for more details!

Surprising Benefits of Curiosity:

  1. Learning new things and being generally curious releases the feel-good chemical, dopamine, in our brains.

  2. Being curious allows you to empathize on a deeper level.

  3. Being curious and asking deeper questions bonds you and builds trust quicker than superficial questions.

But an essential companion to curiosity is deep listening. Listening with your full body. Being fully present. Listening to understand, not listening to respond. This is a learned skill.

How to Listen:

  1. Be present in the moment. If you catch your mind wandering, bring it back to the here and now.

  2. Picture what your prospect is saying, like it’s a movie being played out in your head. You do this when you read books or stories, so it should be pretty natural to tap into this process.

  3. Try to feel what they are saying, as if you are in that situation yourself.

Not only does this help you focus on what they are saying, but you start to truly empathize with what your customer or prospect is saying. Empathy isn’t just about understanding the problems of the business, it’s understanding the decision maker and their point of view, their feelings, and how they arrived at those perspectives.

Better Questions to Ask Your Prospects:

  1. Opens up to tell stories vs one word answers. 

  2. What was the best part about your weekend? 

  3. What are you excited about right now?

  4. What made you fall in love with your spouse? 

  5. What problem do you wish you could solve?

  6. What are you most passionate about?

  7. What would a perfect day look like if all of your problems were solved right now? 

  8. What do you wish you could do more of in your day?