The 5 Whys of Discovery: How to Uncover the Real Sales Pain
- Matthew Earle
- May 13
- 4 min read
Updated: May 17
The 5 Whys of Discovery: How to Uncover the Real Sales Pain
Why Surface-Level Discovery Fails
Every sales team is told to 'dig deeper' in discovery. Yet 80% of deals stall because sellers solve the wrong problem, the one the buyer mentions first, not the one that is really impacting their business, career, or job security.
But the uncomfortable truth is when it comes to discovery, most sales people stop at the surface level problem. The first pain mentioned, the loudest complaint, or the obvious symptom.
This surface level problem that has been uncovered? Well, that’s not the real issue. It's not the problem that will make the key decision makers within the buyer decide to make a change.
The business case and ROI will be met with a 'so what'. Its a pain, sure, but we have a million and one other problems that are a higher priority.
"Let's revisit this when it does become a priority"
Why does this problem not drive urgency and action? Because it’s just the tip of the iceberg.
Why Most Discovery Calls Fail To Identify Real Opportunities
Because most sellers have not been coached to get to the real root cause of the problem.
Its uncomfortable. They risk upsetting the buyer.
Most sellers latch on to the first problem they hear, especially if it confirms one of their own assumptions or biases, then rush to propose a solution to that surface level issue.
That’s not discovery. That’s diagnosis without examination.
This leads to:
Solving the wrong problem
Result: Stalled or no sale
Weak commercial impact
Result: Lower value or heavily discounted to win the deal
No urgency from the buyer
Result: Inaccurate pipeline and missed targets.
And when there’s no urgency? Deals stall or quietly die.
Enter: The 5 Whys Technique
The “Five Whys” is a method borrowed from lean manufacturing and problem-solving frameworks, but it’s one of the most powerful tools in a salesperson’s kit.
You take the first problem the buyer mentions and ask:
“Why is that a problem?”
Then repeat the process up to five times.
Each “Why” takes you closer to:
The commercial impact
The broader organisational ripple effects
The emotional or political pressure the buyer faces
The 5 Whys: A Real-World Example
This is a sales call that one of my team ran several years ago. We had prepped to follow the 5 whys approach once during the call, and it went something like this:
Seller: So why is a manual ordering process a problem for your business?
Buyer: Well mistakes can be made on data entry.
Seller: Why is that a problem #1
Buyer: Purchase order numbers may be entered into our system incorrectly.
Now this is where most sales people would stop. Errors are made which is annoying and probably costs them time. An automated solution would eradicate those.
But my seller persisted:
Seller: Why is that a problem #2
Buyer: Well, the invoice won't match the order in our ERP.
Seller: Why is that a problem #3
Buyer: If we can't match the invoice to the order we can't charge our customer.
Seller: Why is that a problem #4
Buyer: If we can't charge the customer, their account goes on block.
Seller: Why is that a problem #5
Buyer: They will be unable to order from us, and will go to a competitor. And some of our corporate customers are worth millions.
So the 5 whys had uncovered that the real problem from a lack of automation was the risk of losing corporate customers, who may or may not return, that had could have a multi-million pound impact on revenue. That would be a problem all of the C-Suite would be concerned about.
What This Changes in Sales Conversations
When you train your team to use the 5 Whys:
They uncover multi-layered pain
They avoid biased assumptions
They shift the buyer’s thinking from “nice to have” to “need to solve now”
You’re not just selling a product. You’re solving a priority-level business problem.
If your team’s discovery calls aren’t revealing the real commercial pain, it’s time to go deeper.
Surface pain doesn’t sell. Real pain creates urgency.
The 5 Whys of Discovery: How to Uncover the Real Sales Pain
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