SQUARE PARALLEL POINT OF VIEW
ENTERPRISE TECHNOLOGY · TECHNICAL REVENUE
Most stalled enterprise technology deals don't have a product problem. They have a WHY problem.
If the technology worked, the customer was engaged, and the demo went well, what was missing?
02 / DEMO ≠ DISCOVERY
INTEREST · PROBLEM · PRIORITY · WHY
Customers can like the technology, praise the demo, ask thoughtful questions, and still have no compelling reason to change anything. Technical enthusiasm is not the same thing as business priority.
A demo explains capabilities. It helps the customer understand how the technology works, what makes it different, and what might be possible if they deployed it.
Discovery uncovers the business and technical problem, who is affected, what the current state costs, why it matters now, and what happens if the organization does nothing.
If you haven't discovered why the problem matters, who cares about it, and why it must change now, you haven't discovered the deal.
03 / HAPPY EARS
ENTHUSIASM · INTENT · AUTHORITY · REALITY
Technical people like technology. They'll ask questions, challenge the architecture, bring colleagues into meetings, ask for another demo and maybe even agree to a POC.
“This is much better than what we're using.”
Or: “We could definitely use this.”
“We're going to buy it.”
That's the leap. Interest becomes intent without the customer ever actually making it.
I once went shopping for a BMW with my 12-year-old son. He was already a car fanatic and knew an incredible amount about cars.
The salesperson loved him. They talked features, performance and technology. My son was completely engaged.
The salesperson probably thought the conversation was going great.
There was only one problem.
My son was 12.
He would have bought the car in a second.
I did. And the salesperson wasn't talking to me.
The technical person who loves your product may be an important champion. Their enthusiasm matters. Their technical judgment matters. Their support may be essential.
But enthusiasm alone doesn't tell you who owns the business problem, who controls the money, who can establish priority, or who ultimately decides whether the organization will act.
If all of your energy is going into the person who loves the technology, you may be having a terrific conversation with the enterprise equivalent of my 12-year-old son.
Don't confuse the person who loves your product with the person who can make the business decide to buy it.
04 / NEED ≠ PRIORITY
NEED · PRIORITY · ACTION · CHANGE
Enterprise organizations have dozens—sometimes hundreds—of legitimate problems competing for the same money, people, executive attention, and capacity for change.
A technical team may genuinely need what you're selling. The existing environment may be inefficient, difficult to manage, expensive, risky, or simply outdated.
None of that guarantees the organization will act.
Before money moves, the problem has to become important enough to compete successfully against everything else the enterprise could spend its time and money on.
That's the difference between identifying need and establishing priority.
The current state is inefficient, expensive, risky, difficult, or limiting what the organization wants to accomplish.
The impact is understood, stakeholders care, consequences are visible, and solving it competes successfully for executive attention.
Budget, people, political capital, implementation resources, and executive sponsorship are committed to changing the current state.
In enterprise technology, your solution is competing for more than market share. It is competing for organizational attention and resources. Sometimes the strongest competitor isn't another product at all.
Finding a problem gives you something to discuss. Establishing why that problem matters enough to change gives the customer a reason to act.
05 / THE SALES CYCLE IS BACKWARDS
DISCOVERY · VALUE · VALIDATION · DECISION
Too many enterprise sales motions begin by showing the technology, proving the technology, pricing the technology—and only later trying to establish why the customer should buy it.
The customer asks for a demo, so we give a demo. They ask for a POC, so we run a POC. They ask for pricing, so we send pricing.
Every request feels like forward motion.
But if we haven't established the business problem, its impact, who cares about it, why it is a priority, and what success must look like, we're moving through sales stages without necessarily moving the customer toward a decision.
What features do they need?
What should we demo?
What should we prove in the POC?
What price will they accept?
What problem must change?
What is that problem costing them?
Who cares enough to act?
What evidence will support a decision?
By the time a customer reaches technical validation, the team should already understand what problem is being solved, why it matters, what the desired outcome is, and what evidence is required to support the buying decision.
The POC should validate a decision that is already taking shape—not become an expensive attempt to discover whether there is a deal.
Don't use the sales process to discover whether the customer has a reason to buy. Discover the reason first—then use the process to validate it.
06 / A POC IS NOT A TEST DRIVE
SUCCESS CRITERIA · EVIDENCE · DECISION
A POC should answer specific technical questions that matter to a buying decision. It should not be an open-ended opportunity for the customer to spend more time with your product.
Earlier, the 12-year-old boy could answer every discovery question about the BMW. He could tell us which model he wanted, the color, the options, and exactly what he liked about it.
We could put him behind the wheel—at least hypothetically—and prove that the car performs exactly as promised.
None of that changes the fundamental problem: he isn't a qualified buyer.
Enterprise POCs fail for the same reason. Technical enthusiasm is not the same thing as organizational commitment.
The evaluation begins without a clearly defined business decision or agreed success criteria. The technology becomes the center of the process.
The evaluation begins with a defined problem, agreed outcomes, explicit success criteria, and an understanding of how the evidence will be used in the buying decision.
What condition in the current state needs to change?
What specific evidence would demonstrate that change is possible?
What did the evaluation actually prove against those criteria?
Does the evidence support moving forward with the change?
If the seller and customer cannot agree on what constitutes success before the POC begins, the evaluation has no objective finish line.
That creates one of the most common enterprise deal traps: the technology keeps being evaluated because nobody knows what evidence is sufficient.
Every success criterion should answer: “If we prove this, what customer concern or buying question does it resolve?”
A successful POC doesn't prove that your product works. It proves that your product can produce the evidence required for the customer to make a decision.
07 / WHEN THE DEAL STALLS
DIAGNOSE · DON'T JUST REACT
A stalled deal creates pressure to do something. Another meeting. Another demo. Another follow-up. Another concession. But more activity doesn't necessarily solve the reason the customer stopped.
When momentum disappears, the instinct is often to re-engage the customer with something new: another demo, a deeper technical session, a revised proposal, a discount, or an executive meeting.
Those things can be useful—but only if they address the reason the deal stalled.
Before deciding what to do next, diagnose what the customer still doesn't know, believe, prioritize, or have permission to do.
of the time, when a purchase decision stalls, sellers go back to the beginning.
When sellers return to the beginning, 84% of the time the approach backfires. Repeating the sales motion doesn't fix the reason the decision stalled. It asks the customer to repeat a process that already failed to create enough conviction to change.
Don't restart the sales process. Go backward only far enough to find what was never established.
Can the customer clearly describe what is wrong with the current state—or are we solving something they merely find interesting?
Is the consequence visible in cost, risk, productivity, revenue, customer experience, compliance, or another meaningful outcome?
What makes this problem important enough to compete successfully for budget, people, executive attention, and organizational change?
Is the problem connected to someone who can mobilize resources and navigate the internal decision—or only to people who like the product?
Has the customer defined what must change and what evidence would give the organization confidence to move forward?
Who must agree, what evidence do they require, what alternatives exist, and what organizational commitments are necessary to change?
That question starts with our desire to advance the opportunity.
A better question is: “What does the customer still need in order to make the next commitment?”
Sometimes the answer is technical evidence. Sometimes it is economic justification. Sometimes it is executive sponsorship. And sometimes the answer is that the problem simply isn't important enough.
A stalled deal doesn't always need another sales action. It needs an accurate diagnosis of the commitment the customer has not yet made.
08 / THE REAL MEASURE OF PROGRESS
ACTIVITY · EVIDENCE · DECISION
Enterprise sales teams measure meetings, demos, POCs, proposals, and pipeline stages. Those activities may be necessary. But none of them, by themselves, mean the customer is getting closer to a decision.
Progress happens when the customer becomes more capable, more confident, or more committed to making a decision.
The problem becomes clearer. The impact becomes more important. Stakeholders align. Success criteria become explicit. Technical risk is reduced. The business case strengthens. The organization becomes more willing and able to change.
Enterprise technology deals don't usually stall because the customer needs to see more product. They stall when the organization hasn't established enough reason, evidence, alignment, or confidence to change.
A practical framework for translating technical capability into operational change, business outcomes, executive metrics, and economic value.
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