EP26 | Scott Cowley
Why Deals Really Stall: The 'Three Whys' Framework for Truly Understanding Your Buyer
Some episodes feel tactical.
This one feels foundational.
When Scott Cowley—fractional VP, advisor, coach, and “top-performer-turned-non-performer-turned-top-performer”—came to the MySalesCoach studio, he and Mark Ackers dug into the exact framework that rebuilt his sales career after the most painful chapter of it: nine months at a cybersecurity company without closing a single deal.
His biggest lesson?
“You have to deeply understand why someone is buying your product. And I break it down into this three whys:Why buy anything?
Why buy now?
Why buy your product?”
Scott learned this the hard way—and what he shares in this episode is the difference between average, inconsistent sellers and top performers who always hit their number.
Below are the three key actionable lessons from this conversation—each tied to a challenge, an insight, a direct quote, and the fix.
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The 3 Key Lessons
Lesson 1: Most Sellers Skip the First Why—and It’s Why Deals Die Early
Challenge:
Most reps jump straight into pitching features, benefits, and differentiators… without ever establishing whether the buyer should change anything at all. Scott did this for nine months straight—without a single closed deal.
Insight:
If a buyer can continue as they are and nothing breaks, nothing slows, nothing hurts—they won’t change. They won’t even stay in the conversation long enough to hear why they should buy you.
Scott put it simply:
At the start of his career, he “understood what the product did… but I had no idea why someone would pay two analyst salaries for this product.”
“Why buy anything? Why do any change at all? Because if an organisation could have their pain solved without ever talking to you… they would.”
The Fix:
Push early. Push hard. Push honestly.
Ask the uncomfortable questions most sellers avoid:
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“Why can’t you keep doing what you’re doing now?”
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“What breaks if nothing changes?”
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“Who cares about this problem more—the business or just you?”
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“What happens if you wait 12 months?”
If the buyer can’t articulate the “why buy anything,” you don’t have a deal—you have a polite conversation.
Lesson 2: “Why Buy Now” Is the Real Deal-Killer—And It’s Where Most Reps Get Hurt
Challenge:
Even when buyers agree they need something, they rarely know when they need it.
And sellers rarely question it.
This is where the second Why—Why Buy Now—becomes essential.
Scott shared a painful example from a client selling to Premier League clubs:
“They got completely wrong the ‘why buy now.’ The budget’s already assigned. They had to wait an entire year—because they messed up the timing.”
Insight:
Seasonality, budgeting cycles, planning rhythms—these define urgency, not pain alone.
Even if the buyer loves your product, mis-timing the moment means you’re waiting months—or even years—for a real chance to sell again.
“Why buy now is probably the hardest. It’s the one the buyer will struggle the most to answer.”
The Fix:
Master your customer’s calendar—better than they do.
Ask:
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“When does budget reset?”
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“When do priorities get locked for next year?”
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“If we work backwards from your go-live date, when do you actually need a decision?”
And map it mathematically:
Desired go-live → Implementation length → Procurement buffer → Budget approval window → Decision deadline
Most buyers haven’t done their homework on this.
Great sellers do it for them.
Lesson 3: The Only Why Most Sellers Know—“Why Buy You”—Is the Least Important
Challenge:
Reps over-index on product knowledge.
They obsess over differentiation.
They pitch features to people who aren’t ready to hear them.
Because it’s the only Why they feel qualified to answer.
Scott sees this constantly:
“Most people are really good at one of the three whys, and it’s the last (and least important) one of the three… ‘Why buy your product?’”
Insight:
The problem is, these Whys need to go in sequence, and this one comes last.
Buyers don’t get to “why you?” until:
- They decide they must change
- They decide they must change now
If you skip the first two Whys, you’re leaving deals closing up to chance.
And its key to remember this:
“No matter how good your product is… you’re only solving one percent of their pain. They have thousands of problems every day.”
The Fix:
Save “Why Us” for the right moment.
Early in the cycle, shift your language from product to buyer reality.
Scott’s Sunday Night Test brings this to life:
“Imagine your customer lying awake at 2am. How are they describing their problem to themselves? Use their language, not yours.”
Your job is not to impress.
Your job is to translate.
Focus on the first two Whys until the buyer invites you into the third.
Lesson 4: Buyers Make the Decision—Sellers Only Influence the Journey
Challenge:
Sellers often believe they can will a deal across the line with pressure, persistence, or persuasion.
It’s false.
And it’s why they burn out.
Insight:
The buyer makes the decision.
The seller guides it—nothing more, nothing less.
“A salesperson doesn’t decide when a sale happens. Only the buyer does.”
The Fix:
Detach from outcome. Attach to influence.
Replace:
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“How do I close them?”
With:
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“How do I support them in deciding?”
When you start selling with buyers instead of at them, your win rates jump.
Conclusion: Master the First Two Whys, and You’ll Outsell 90% of Reps
Scott’s entire transformation—from top performer, to fired, to framework-builder—came from one truth:
Great sellers don’t start with “Why us?”
Great sellers start with Why anything? and Why now?
If you master those two questions, every conversation becomes clearer.
Your qualification becomes sharper.
Your urgency becomes real.
And your pipeline becomes honest.
The Three Whys aren’t a technique.
They’re a discipline.
Turn the Three Whys Into Muscle Memory
If your team:
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Struggles with urgency
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Struggles qualifying
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Struggles with buyer alignment
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Struggles converting interest into revenue
…they don’t need more tools.
They need sales coaching.
👉 Book a call with MySalesCoach today to give your team the frameworks, skills, mindset and confidence) to sell the way elite reps do.