Sales Pros, Go From Interrogation To Insight

How To Ask Questions That Uncover Client’s Deepest Desires

Most sales professionals know they should ask questions to better understand their clients. It’s common advice.?

Yet, in reality, few are actually good at it. Most jump straight into presenting their solutions without first understanding their clients’ core concerns, fears, or desires. They assume a one-size-fits-all approach will work, but it rarely does.

It’s the rare few who understand the value of slowing down the process so that can gain a clear understanding of clients’ motivations, fears, and desires.?

Do this effectively, and you quickly earn trust, and eventually, their business.?

This starts with asking better questions.

How do you effectively do this?

Let’s start with what NOT to do…avoid asking a series of “why?” questions.?

What??

Isn’t it common knowledge that we should “Start with why?” to understand what makes people tick?

Yes, but, here’s the problem:?

When you ask someone a series of “why” questions, it often feels like an interrogation.?

When you and I were younger, and we did something that adults perceived was wrong or "bad", what type of questions that they ask us:

"Why did you do that!”

“Why would you think that’s okay?

“Why are you behaving this way?”

“Why are you being so difficult?”

That's the reason many people instinctively become defensive when we ask them “why?” It’s like shining a spotlight on their discomfort, and instead of opening up, they shut down.

Consider this scenario…

Imagine I’m talking with a prospective client who wants to hire me for coaching.?

Me: Why did you reach out for help with your presentation skills

Client: I feel like I’m not connecting with my audience.

Me: Why do you think that’s happening?

Client: Maybe because I’m not confident in my delivery.

Me: Why aren’t you confident?

Client: I’m just not sure people are getting what I’m trying to say.

Me: Why do you want them to get it?

Client: Well, I don’t want my message to just fall flat…

Me: Why does it matter so much to you?

Client: It just… it’s exhausting explaining it over and over again.

How would you feel at the receiving end of this??

Probably frustrated, annoyed, and defensive.

Compare this to a more effective approach using variations of “why-type” questions:

Me: What motivated you to meet with me about improving your presentation skills?

Client: Well, I feel like I’m not connecting with my audience as well as I could, and it’s impacting how my message is received.

Me: What do you think is getting in the way of that connection?

Client: I guess it’s a lack of confidence in delivering my message effectively

Me: How do you believe your impact will improve if you felt more confident

Client: I think people would feel more at ease, listening to me, and would begin to trust me more

Me: That’s interesting. How do you want to impact your audience?

Client: I want them to leave feeling inspired and motivated to take action on what I shared. I don’t want them to just listen and forget everything when they walk out.

Me: What would it mean to you if you could achieve that level of impact every time?

Client: It would be huge for me. I’d feel fulfilled knowing that my work actually matters to people. It would be like turning my presentations into moments that change lives, instead of just being more noise in their day

See the difference??

Instead of hammering away with “why,” I asked "what" and “how"-type questions. The second approach gently leads the client deeper into their motivations and emotions. It creates space for a meaningful conversation instead of an interrogation.

If you’re in sales, coaching, or any field where you offer solutions, remember this:?

It’s not about delivering the perfect pitch—it’s about connecting with the person in front of you.?

This means understanding their motivation, their desires, and their fears.

Skip the constant “why” and instead explore their challenges by using variations of the question. You’ll help them discover what truly matters, and in turn, they’ll feel heard and understood.

Your challenge:?

Create five “why-type” questions you could ask to make your conversations more impactful.

Share your ideas in the comments box.