One of the most valuable lessons I’ve learned about sales didn’t come from a sales trainer, a sales book, or even a sales conversation.
It came from an insurance advisor.
Years ago, I was involved in a small plane incident that could have ended very differently than it did. Thankfully, everyone was okay, but it was one of those moments that forces you to pause and think about things you normally push to the back of your mind. A few hours later, my phone rang. It was my insurance advisor, Mark Gibson.
Mark wasn’t calling to check a box or update a file.
He was calling because he knew something I didn’t fully appreciate at the time.
Sometimes people need help seeing the risks they’re not looking at.
The conversation started simply enough. He asked whether I thought I had enough life insurance if something had happened to me. As I thought about my wife and son, I realized the answer was no. We agreed to increase the coverage and I figured we were done.
But Mark wasn’t done.
He asked me what would happen if I survived but could no longer work.
What if I couldn’t stand on stage anymore?
What if I couldn’t speak?
What if I was permanently disabled?
I remember thinking it was a terrible question.
It was also exactly the right question.
The conversation continued as he introduced disability insurance and eventually critical illness insurance. Every question forced me to consider scenarios I had never seriously explored before. By the end of the conversation, I wasn’t buying insurance products. I was protecting future outcomes, reducing risks, and addressing blind spots I didn’t even know existed a few hours earlier.
Looking back, that conversation taught me something that applies directly to sales, leadership, consulting, coaching, and business development.
The best advisors don’t just solve the problems people bring to them.
They help people discover the problems they haven’t seen yet.
Why Most Discovery Conversations Stay Too Close to the Surface
One of the challenges I see in sales today is that many discovery conversations never get past the obvious.
A prospect explains the challenge they’re facing. The salesperson asks a few qualifying questions. Then they move directly into presenting a solution. On the surface, it feels productive because everyone is moving quickly. The client gets answers. The salesperson gets an opportunity to present. The conversation feels efficient.
The problem is that efficiency and effectiveness are not always the same thing.
When we rush through discovery, we often end up solving the symptom instead of understanding the cause. We address the issue the client can see while completely missing the issue that’s creating the problem in the first place.
Think about how often this happens in everyday life. Someone goes to a doctor with a headache. The headache feels like the problem, but a great physician doesn’t stop there. They ask questions. They investigate. They look for patterns. They explore what might be happening beneath the surface.
The same principle applies in business.
The first problem a client presents is rarely the entire story.
The Role of Blind Spot Questions
One of the things that separates trusted advisors from average salespeople is their ability to ask what I call blind spot questions.
These are questions designed to uncover risks, opportunities, assumptions, and consequences that the client may not have fully considered.
They’re not meant to create fear.
They’re meant to create awareness.
Blind spot questions help people think beyond the immediate challenge and consider the bigger picture. They shine a light into areas that have been ignored, overlooked, or simply never explored.
The interesting thing about blind spot questions is that they often create silence.
Not uncomfortable silence.
Productive silence.
The kind of silence that happens when someone suddenly realizes there’s a bigger issue at play than they originally thought.
That’s often where the most valuable part of the conversation begins.
How Great Advisors Create Value Before Presenting Solutions
One of the reasons Mark’s questions were so effective was that he wasn’t trying to sell me a product.
At least not initially.
He was helping me understand the consequences of inaction.
He was helping me see risks that existed whether I chose to acknowledge them or not.
That’s an important distinction because many sales professionals try to create value by talking about their solution. Great advisors create value before the solution is ever discussed. They create value through insight. They create value through perspective. They create value by helping clients see their situation more clearly than they could before the conversation started.
That’s what transforms a sales conversation into an advisory conversation.
When people gain clarity, they naturally become more open to exploring solutions.
When people discover a blind spot, they become motivated to address it.
And when they arrive at those conclusions themselves, they don’t feel sold.
They feel helped.
What Blind Spot Questions Look Like in Business
A few years ago, I was speaking with a sales leader about their CRM system.
At first glance, everything seemed fine.
They had invested in the technology. The system was in place. The team had access to it. From a distance, it looked like the problem had already been solved.
Then I asked a simple question.
“Are your salespeople actually using it consistently?”
The answer was something along the lines of, “Sort of.”
That’s where the conversation became interesting.
The next question was whether they knew what happened to their pipeline when a salesperson left the company. Most organizations lose a significant portion of customer intelligence, relationship history, and future opportunity visibility when information isn’t being consistently documented.
The room got quiet.
Not because anyone disagreed.
Because they had never really thought about it.
Suddenly we weren’t talking about software anymore.
We were talking about revenue risk.
We were talking about forecasting accuracy.
We were talking about employee turnover.
We were talking about the hidden costs that existed beneath the surface.
That’s the power of a good blind spot question.
It changes the conversation from features to consequences.
Why Listening Matters More Than the Question Itself
Whenever people hear about discovery frameworks and needs analysis, they often focus on the questions.
What should I ask?
How should I ask it?
What sequence should I follow?
Those things matter.
But there’s something even more important.
Listening.
One of the challenges many of us face is that we’re often listening just enough to prepare our next response. We hear a portion of what someone says, our brain immediately starts processing an answer, and before they’ve even finished speaking we’re already preparing where we want the conversation to go next.
I’ve been guilty of it myself more times than I’d like to admit.
The problem is that when we’re focused on our response, we stop being fully present.
And when we stop being fully present, we miss valuable information.
We miss emotional cues.
We miss concerns.
We miss opportunities to ask follow-up questions.
We miss the blind spots hiding inside the conversation.
The best discovery conversations don’t happen because someone follows a script perfectly.
They happen because someone is genuinely curious enough to stay present.
Real Rapport Is Presence
People often talk about rapport as if it’s a communication technique.
They talk about matching and mirroring.
They talk about personality styles.
They talk about body language and voice tonality.
While some of those things can be helpful, I’ve come to believe that real rapport is much simpler than that.
Real rapport is being fully present.
It’s giving someone your complete attention.
It’s creating an environment where they feel heard, understood, and respected.
It’s suspending your agenda long enough to truly understand theirs.
When people feel genuinely listened to, they share more.
When they share more, deeper challenges emerge.
When deeper challenges emerge, opportunities for meaningful value creation become visible.
That’s why listening is not a passive skill.
It’s one of the most powerful business development tools available.
Building Better Discovery Conversations
One of the reasons great advisors consistently outperform average salespeople is that they understand discovery isn’t about collecting information.
It’s about creating insight.
The goal isn’t simply to learn about the client’s situation.
The goal is to help the client understand their own situation more clearly.
That requires thoughtful questions.
It requires curiosity.
It requires business acumen.
And most importantly, it requires the willingness to ask questions that might be a little uncomfortable.
Because those are often the questions that matter most.
The questions that uncover hidden risks.
The questions that expose assumptions.
The questions that reveal opportunities.
The questions that help people see what they’ve been missing.
That’s where trust gets built.
That’s where value gets created.
And that’s where the journey from salesperson to trusted advisor truly begins.
Questions to Reflect On
- What blind spot questions could you add to your discovery conversations?
- Are you spending more time preparing responses or truly listening?
- What risks, opportunities, or assumptions might your clients be overlooking?
- How often do your conversations create new insights instead of simply exchanging information?
- What would change if your goal was to help clients see what they cannot currently see?
Ask the questions that help people discover what matters most.
