One of the most useful sales lessons I ever learned did not come from a sales training course, a sales book, or a formal discovery conversation. It came from my insurance advisor.
Years ago, I was involved in a small plane incident. It could have ended much differently than it did. Thankfully, everyone was okay, but it was the kind of experience that makes you think about the risks you normally push out of your mind.
A few hours later, my phone rang. It was my insurance advisor, Mark.
Mark was not calling to update a file. He was calling because he understood something I had not fully appreciated yet: people often need help seeing the risks they are not looking at.
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 assumed the conversation was finished.
Then Mark asked a better question.
What would happen if I survived but could no longer work? What if I could not stand on stage anymore? What if I could not speak? What if I was permanently disabled?
I remember thinking it was a terrible question to have to answer. It was also exactly the right question. Mark understood the power of selling risk through asking tough seldomly asked questions.
That conversation led to disability insurance and eventually critical illness insurance. More importantly, it forced me to think through scenarios I had not seriously considered. By the end of the call, I was not thinking about insurance products. I was thinking about my family, my income, my ability to work, and the consequences of being unprepared.
That is what good advisory work does. It helps people see something important before the cost of missing it becomes obvious.
Why Most Discovery Conversations Stay Too Close to the Surface
Many sales discovery conversations stay close to the surface. A prospect explains the issue they are facing, the salesperson asks a few qualifying questions, and then the conversation quickly moves toward a solution.
It can feel productive because everyone is moving quickly. The client gets answers. The salesperson gets an opportunity to present. The meeting feels efficient.
The problem is that speed can hide weak discovery.
When we rush, we often solve the visible symptom without understanding what is causing it. We respond to the problem the client can already see and miss the issue underneath it.
A client may say they need a better CRM, but the real problem may be poor sales management discipline. They may ask for sales training, but the deeper issue may be inconsistent coaching. They may complain about lead quality, but the actual constraint may be weak follow-up, unclear positioning, or poor qualification.
The first problem a client names is important, but it is rarely the whole story.
The Role of Blind Spot Questions
Blind spot questions help clients examine risks, assumptions, consequences, and opportunities they may not have fully considered.
They are not scare tactics. They are not manipulation. Used properly, they help the client think more clearly about the decision in front of them.
A good blind spot question might explore:
- what happens if the issue is not addressed
- what the current problem is already costing the business
- who else is affected by the decision
- what assumptions the client may be making
- what risks are being underestimated
- what opportunities are being missed
- what would break if the business grew quickly
- what information is missing from the current view of the problem
These questions often create silence. That silence is not a bad sign. It usually means the client is thinking.
In many sales conversations, the most useful moment happens after the client pauses and says, “I had not thought about it that way.”
How Great Advisors Create Value Before Presenting Solutions
Mark’s questions worked because he helped me understand the consequence of inaction before he talked about a product. He helped me see a risk that already existed, whether I wanted to look at it or not.
That distinction matters.
A lot of salespeople try to create value by explaining their solution. Strong advisors create value earlier in the conversation by improving the client’s understanding of the problem.
That may mean helping the client see a risk more clearly. It may mean connecting their current challenge to a future consequence. It may mean showing them that the issue they named is only one part of a larger pattern.
When clients gain that kind of clarity, they become more open to exploring options. They do not feel pushed toward a product. They feel better informed about a decision they need to make.
What Blind Spot Questions Look Like in Business
A few years ago, I was speaking with a sales leader about their CRM system. On the surface, the company appeared to have addressed the issue. They had invested in the technology, the system was live, and the sales team had access to it.
So I asked a simple question: “Are your salespeople using it consistently?”
The answer was, “Sort of.”
That answer opened up the real conversation.
We started talking about what happens when a salesperson leaves the company and key account information lives in their head instead of the CRM. Relationship history disappears. Future opportunities become harder to see. Forecasting becomes less reliable. The next person assigned to the account starts with a partial picture.
At that point, we were no longer talking about software adoption. We were talking about revenue risk, management discipline, customer intelligence, and the cost of poor documentation.
That is the value of a good blind spot question. It changes the quality of the conversation. The buyer is no longer evaluating a tool or a feature in isolation. They are looking at the business consequence attached to the behaviour.
Why Listening Matters More Than the Question Itself
When salespeople study discovery, they often focus on the questions:
- What should I ask?
- How should I ask it?
- What sequence should I follow?
- What should I ask next?
Those things matter, but the question list is not enough. The quality of discovery depends heavily on whether the salesperson is actually listening.
Most of us have been guilty of listening just long enough to prepare our next response. The client says something important, and instead of staying with it, we start thinking about our next question, our recommendation, or the point we want to make.
That is where opportunities get missed.
The client may reveal a concern indirectly. They may hesitate before answering. They may use a phrase that exposes a deeper issue. They may describe a political problem inside the organization without naming it directly.
If the salesperson is focused on getting through the script, those clues disappear.
Better discovery requires enough presence to notice what the client says, what they avoid saying, and where their answers become vague, cautious, or emotional.
Real Rapport Is Presence
Sales training often treats rapport as a technique. People talk about matching and mirroring, personality styles, body language, and tone. Some of that can be helpful, but rapport is much simpler at its core.
Rapport is built when the client feels that you are actually paying attention.
That means giving them enough space to think, asking follow-up questions based on what they just said, and suspending your own agenda long enough to understand theirs.
When people feel heard, they usually share more. When they share more, the real problem has a better chance of surfacing. That is why listening is not a passive skill. In business development, it is often the difference between a shallow opportunity and a serious advisory conversation.
Better Discovery Creates Better Decisions
Strong advisors understand that discovery is not just about collecting information from the client. It is also about helping the client understand their own situation more clearly.
That requires business acumen, curiosity, and the willingness to ask questions that may be uncomfortable in the moment but useful to the decision.
A blind spot question should never be asked to make the client feel foolish. It should help them examine something important that has not been fully considered.
For example:
- “What happens if this problem continues for another six months?”
- “Who feels the impact of this issue besides your sales team?”
- “What information would you lose if your top salesperson left tomorrow?”
- “What assumptions are you making about why the pipeline is stalling?”
- “Where does this issue show up in the customer experience?”
- “What risk would your CFO be most concerned about here?”
- “What has to change internally for this solution to actually stick?”
Questions like these move the conversation beyond surface-level need. They help the client think through consequences, ownership, risk, and action.
Questions to Reflect On
If you want to improve your discovery conversations, start by looking at the questions you ask and the way you listen.
Consider:
- What blind spot questions could you add to your discovery conversations?
- Are you listening for the client’s full meaning, or preparing your next response?
- What risks, assumptions, or consequences might your clients be overlooking?
- Do your questions help clients gain new insight, or do they simply help you collect information?
- What would change if your goal was to help clients see the issue more clearly before presenting a solution?
The strongest sales conversations do more than identify a need. They help the client understand what is really at stake.
That is where trust begins.
