Price the Job, Not the Tool
Part 3 - The Deconstruction Toolkit: Finding the True Outcome
Chapter 5: The Intellectual Scalpel: Deconstructing Value with Socratic Questioning
The transition from a tool-based subscription to an agent-based outcome contract is not a sales process; it is a diagnostic one. The most valuable conversation you will ever have with a customer is the one that happens before you ever mention your product. In the old model, the goal of a salesperson was to secure a “demo,” to show off the features of their tool, to prove its potential. In the new model, the goal is to secure a “diagnosis,” to understand the fundamental problem, to identify the outcome.
This requires a completely different skillset. It’s not about persuasion; it’s about precision. It’s not about “solution selling”; it’s about “problem un-packing.” You must become an expert at deconstruction, at breaking down a customer’s complex, messy, and often misunderstood “need” into its most basic, foundational truths.
This is an act of First Principles Thinking. Rather than accepting the customer’s self-diagnosis at face value—rather than reasoning by analogy (”My competitor has a chatbot, so I need one too”)—you must force the conversation back to the fundamental building blocks of the problem.
The single most powerful tool for this deconstruction is not a piece of technology, but a method of inquiry that is over two thousand years old: Socratic Questioning.
Named for the classical Greek philosopher, Socratic Questioning is a disciplined, conversational, and often deeply uncomfortable approach to thinking. It is not a random volley of “why” questions; it is a systematic, probing process designed to uncover underlying beliefs, reveal hidden assumptions, and test the very foundation of an assertion. It is the intellectual scalpel required to cut through the conventional wisdom, polite fictions, and inherited assumptions that obscure the real job-to-be-done.
In this new economy, the “outcome-based” sales leader is not a slick presenter. They are a master of Socratic Questioning. Their job is to guide the customer through this process, to help them dismantle their own problem, and to arrive—together—at a shared, fundamental truth.
Let’s see this scalpel in action.
Imagine a new sales conversation. The customer, a VP of Customer Service, opens with what they believe is the solution:
Customer: “We’re looking to buy an AI chatbot for our website. I’ve scheduled three demos this week, and I’d like one from you.”
The old salesperson, the SaaS vendor, immediately snaps to attention. “Great! You’ve come to the right place. Our ‘Intel-bot 3000’ is best-in-class. It’s powered by GPT-4o, integrates with 50 platforms, and we can offer you a 20% discount on our enterprise seat license. When can we demo?” This salesperson is selling access to a tool.
The new salesperson, the outcome-based partner, pauses. They set the demo aside and pick up the scalpel. They begin the diagnosis with a simple Question for Clarification.
Partner: “That’s interesting. I’m happy to talk about our capabilities, but before we do, can you tell me why you’re looking for a chatbot?”
Customer: “Well, our support ticket volume is out of control. It’s up 30% this quarter, and our human agents are completely overwhelmed.”
This is the first, crucial pivot. The partner has already moved the conversation away from the solution (a chatbot) and toward the problem (high ticket volume). The job is not “to have a chatbot.” The job is “to reduce the burden on support agents.” Now, the partner can begin to challenge the customer’s hidden assumption: that a chatbot is the right tool for this job.
The partner employs a Question that Challenges Assumptions.
Partner: “That sounds stressful. You’ve assumed a chatbot is the best way to solve that. What if that assumption is wrong? What other ways could you reduce ticket volume?”
Customer: “I’m not sure. I guess we could hire more agents, but we don’t have the budget. The chatbot seems like the cheapest, fastest way.”
Partner: “It might be. But how do you know a chatbot will solve the problem? What if the reason your ticket volume is high is because your product’s new UI is confusing? A chatbot would just be a high-tech, expensive bandage on a bad product. It’s treating the symptom, not the cause.”
The customer is now, for the first time, being forced to think about their problem in a new light. The partner is not selling; they are co-architecting a solution. The next step is to ground the conversation in facts, not feelings. The partner uses a Question that Seeks Evidence and Reasons.
Partner: “Let’s dig into that ticket volume. What is the evidence? Do you know what the top three reasons for those tickets are? Is it ‘password resets,’ ‘shipping status,’ or ‘complex technical failures’?”
Customer: “That’s a good question. Let me pull the report... Okay, it looks like... wow. 52% of all new tickets in the last 30 days are ‘password resets.’ I had no idea it was that high.”
This is the “Aha!” moment. This is the moment of deconstruction. The Socratic method has revealed that the customer’s problem is not “our agents are overwhelmed.” That is a symptom. The true problem is “our password reset process is broken.”
Suddenly, proposing a $50,000-a-month “AI chatbot” to solve this is revealed to be an act of profound malpractice. It’s like using a cannon to kill a mosquito. The customer doesn’t need a complex, conversational AI to handle a simple, transactional task.
The partner can now reframe the entire job.
Partner: “So, the primary job isn’t ‘to have a conversation with a customer.’ The job is ‘to autonomously resolve password resets before they become a support ticket.’ Right?”
Customer: “Yes. Exactly.”
And now, for the first time, the partner can talk about their solution—not as a “chatbot,” but as an agent hired for this specific, measurable job.
Partner: “Okay. We don’t need to sell you our ‘Intel-bot 3000.’ What you need is our ‘Password Reset Agent.’ We can deploy it, and it will autonomously handle that entire workflow. Your customers will get their resets done in 10 seconds, and your team will never even see the tickets. We’ve just eliminated 52% of your problem.”
The customer is floored. The partner hasn’t “won the sale”; they have solved the problem. But how to price it?
The Socratic process has made this simple. The price is no longer a “per-seat” subscription, which is irrelevant. The price is tied directly to the job we just uncovered.
Partner: “And here’s our proposal. Don’t pay us a subscription. It’s meaningless. Your cost for a human agent to handle one password ticket, all-in, is about $10. Our agent can do it for $1. Our price is $1 per autonomously resolved ticket. We only get paid when we successfully get the job done. If our agent fails and the ticket goes to your team, you pay us nothing. We will win only when you win.”
This is the power of the intellectual scalpel. The Socratic method has, in the span of one 15-minute conversation, achieved four things:
It deconstructed the customer’s flawed, solution-based request (”I need a chatbot”).
It challenged the hidden assumptions and dug for evidence.
It identified the true, fundamental job-to-be-done (”resolve password resets”).
It revealed a clear, measurable, and high-value outcome that both parties can agree on and price.
This broad, assumption-challenging approach is the first tool in our deconstruction kit. But it’s not the only one. Socratic Questioning is a scalpel, ideal for cutting a problem open and exploring its breadth. But sometimes, a problem isn’t broad; it’s a deep, linear, and causal chain of failures. For that, we need a different tool. We need a drill.
Chapter 6: Drilling for the Root Cause: The Five Whys of Customer Need
If Socratic Questioning is an intellectual scalpel, designed for the broad, exploratory surgery of deconstructing assumptions, then the Five Whys is its counterpart: it is a high-torque drill, designed for a single, linear, and powerful purpose: to find the root cause.
This technique was developed by Sakichi Toyoda, the founder of Toyota Industries, and it became a cornerstone of the legendary Toyota Production System. It is a simple but relentless iterative methodology used to explore the cause-and-effect relationships underlying a problem. The goal is to peel back the layers of symptoms that obscure the real issue, drilling down vertically through causality until the fundamental, actionable origin of the failure is exposed.
While Socratic Questioning expands the problem space (”What if our assumptions are wrong?”), the Five Whys contracts it. It relentlessly narrows the focus by repeatedly asking “Why?” until the answer is no longer a symptom but a foundational process or policy failure.
This tool is essential for the outcome-based partner because customers rarely, if ever, understand their own root cause. They are experts in their symptoms. They feel the pain of “late deliveries” or “high customer churn” or “low sales.” They will naturally try to hire you to treat that symptom. The SaaS vendor is happy to oblige, selling them a “route optimization dashboard” (a tool) to help with “late deliveries.”
The outcome-based partner, however, knows this is a fool’s errand. Treating the symptom is a low-value, temporary fix. The real, high-value, and permanent solution—the one you can build a business on—is to solve the root cause. The Five Whys is the diagnostic tool you use to find it.
Let’s apply this drill to a new scenario: a mid-sized logistics company.
The Head of Operations calls, and just like our last customer, he opens with a solution:
Customer: “We need a new route optimization platform. Ours is legacy. We’re getting killed on ‘last-mile’ deliveries, and our drivers are complaining. We need a demo of your AI routing tool.”
The SaaS vendor books the demo. The outcome-based partner begins to drill.
Partner (Why #1): “I understand the frustration. But ‘route optimization’ is the solution. What’s the problem you’re trying to solve? Why do you believe you need a new platform?”
Customer (Answer #1): “Because our ‘on-time delivery’ rate has dropped by 15% this quarter. It’s our most important KPI, and we’re failing. Our drivers are getting stuck in traffic, and the current system isn’t adapting.”
This is the surface-level symptom: Late deliveries. A low-value partner would stop here and sell a “route-planning tool.” The partner drills again.
Partner (Why #2): “Why has the rate dropped so suddenly? Has traffic in your city gotten 15% worse in one quarter?”
Customer (Answer #2): “Well... no. The real issue is that we’ve had a huge influx of new residential customers. Our old routes were 90% commercial, B2B. Now we’re doing all these B2C deliveries, and the routes are a mess. The drivers don’t have good drop-off instructions, and they’re spending 10 minutes at each house just trying to figure out where to leave the package.”
This is a critical discovery. The problem isn’t “traffic.” The problem is a fundamental shift in the business model that the old system wasn’t designed for. The symptom is “late deliveries,” but the cause is “inefficient B2C drop-offs.” A slightly better partner might stop here and sell a “driver communication app.” The partner drills again.
Partner (Why #3): “Why is the system generating routes with inefficient B2C drop-offs?”
Customer (Answer #3): “Because the routing system and the ‘customer order’ system are not integrated. Our routing platform was built for B2B; it only knows how to plan for a ‘loading dock.’ The customer’s specific instructions—’leave on back porch,’ ‘code is 1234’—are in our separate e-commerce platform. The drivers have to toggle between two different apps. They plan a route in one, then pull up the order in the other. It’s a manual, chaotic process.”
We are getting deeper. The root cause is not “bad routes”; it’s a broken information pipeline. The data is siloed. The systems don’t talk. This is a technical failure. We could stop here and sell a “systems integration” project. But we are not at the business root cause yet. We are at the technical root cause. We must drill again.
Partner (Why #4): “Why were these two systems, which are mission-critical for your new business line, never integrated?”
Customer (Answer #4): “We tried. We hired a consultancy last year. They quoted us six months and $500,000. The CFO looked at the numbers and said there was no way. The margin on these new B2C deliveries is already razor-thin. We’re barely making money on them as it is. He said, ‘We can’t afford to sink half a million dollars into a 2% margin business.’ So, he vetoed the project, and told us to ‘make it work’ with the current tools.”
This is the heart of the matter. This is the true, foundational problem. The problem is not “late deliveries.” The problem is not “bad routes.” The problem is not “siloed data.” The root cause is that the company’s B2C business line is structurally unprofitable, and they have no economically viable way to fix it.
The CFO made a rational, financial decision. He was given a high-cost, high-risk project (a tool-based solution) to solve a low-margin symptom. The math didn’t work.
But what if we ask “Why” one last time, to get to the core principle?
Partner (Why #5): “Why are the margins so thin that you can’t afford to invest in the core technology to make it work?”
Customer (Answer #5): “Because our pricing is all wrong. We’re charging these new B2C customers based on a simple ‘weight + distance’ model we’ve used for 20 years. We have no idea, when we take an order, if it’s an ‘easy’ delivery (a house on a main street) or a ‘hard’ delivery (a gated community, a 10th-floor apartment). We are flying blind. We are losing money on 30% of our new customers and don’t even know it until it’s too late. The business is fundamentally broken.”
This is the root cause. The job is not “optimize routes.” The job is “ensure profitable B2C delivery.”
The Five Whys has successfully drilled past five layers of symptoms:
Symptom: Late deliveries
Symptom: Inefficient B2C drop-offs
Symptom: Siloed data systems
Financial Symptom: No budget for a high-cost integration project
ROOT CAUSE: An inability to price B2C orders profitably due to a lack of predictive data.
The customer doesn’t need a “route optimization tool.” That’s a low-value, feature-based solution. They need an agent that can predict the true cost of a delivery before the order is even accepted.
Now, the outcome-based partner can make their real pitch, and it has nothing to do with the “AI routing tool” the customer originally asked for.
Partner: “I’m not going to sell you a route optimization platform. It won’t solve your problem. Your CFO is right to block a $500,000 project that just treats a symptom. You have a profitability problem, not a routing problem.
“Here is our proposal. We will deploy our ‘Delivery Profitability Agent.’ It will integrate with your order intake system. Before your sales team ever gives a customer a quote, our agent will analyze the delivery address, the special instructions, and 100 other variables, and it will predict the true, all-in cost for that specific delivery.
“And here is our price. We will not charge you a subscription. We will not charge you for ‘integration.’ Our price will be 2% of the margin you save. We will establish a baseline for your current B2C delivery losses. For every dollar of that loss we eliminate, we get two cents. We will make money only when you stop losing money. We are so confident our agent can solve your root cause that we will take 100% of the performance risk.”
This is a proposal that is impossible to refuse. It directly solves the CFO’s root-cause objection. The “unaffordable” $500,000 project (a cost) has been transformed into a $0 investment with a guaranteed, shared upside (a profit).
The Socratic scalpel and the Five Whys drill are the essential diagnostic tools for getting to this point. They allow you to deconstruct the customer’s world, move past their flawed self-diagnosis, and identify the true, high-value, priceable outcome.
But this process creates one final piece of a puzzle. In both of our examples—the password resets and the delivery margins—we have arrived at a specific, measurable thing to price. But how do we formalize this? How do we move from a verbal agreement to a clear, contractual statement of success? For that, we need a final tool: a way to translate a “job” into a set of precise, measurable metrics.
Chapter 7: From Vague Goals to Hard Metrics: Using Job Maps and CSS
The diagnostic process is complete. Our Socratic scalpel has cut away the customer’s flawed assumptions, and our Five Whys drill has exposed the true root cause. We have successfully moved the conversation from a low-value tool (”I need a chatbot”) to a high-value job (”I need to eliminate password reset tickets”). We have identified the outcome.
But this is not enough.
“Eliminate password reset tickets” is a clear goal, but it is not a contract. “Ensure profitable B2C delivery” is a powerful objective, but it is not a metric. Before we can build a new commercial model, we must translate these qualitative, abstract “jobs” into a set of precise, quantitative, and irrefutable metrics. We need the formal language of success.
The Jobs-to-be-Done framework provides two specific, operational tools for this.
First, we use a Job Map. A Job Map is a simple, visual, and solution-agnostic tool that deconstructs any customer job into its universal, component steps. Most jobs follow a similar pattern: a customer must Define their goal, Locate the inputs, Prepare the environment, Confirm they are ready, Execute the main task, Monitor the results, Modify as needed, and Conclude the job.
By mapping the customer’s job—whether it’s “resolving a password reset” or “quoting a B2C delivery”—against these steps, we can pinpoint exactly where the value is created and where the failures lie.
Second, for each step in that map, we create Customer Success Statements (CSS). These are the crown jewels of the entire process. A CSS (also called a Desired Outcome) is a precise, solution-agnostic, and quantifiable statement that captures exactly how a customer measures value.
These statements are not vague goals. They are rigorously structured metrics, typically in one of two formats:
Practical (PJTBD) Format:
[Verb]+[Object of control]+[Contextual clarifier](e.g., Compare actual progress to planned progress).Outcome-Driven (ODI) Format:
[Direction]+[Metric]+[Object of control](e.g., Minimize the time it takes to compare actual progress to planned progress).
Let’s apply this to our logistics company’s root-cause job: “ensure profitable B2C delivery.” By mapping this job, we can generate a set of CSS that will become the basis for our contract:
Minimize the time it takes todetermine the optimal delivery route.Minimize the likelihood ofencountering an un-planned delivery-site obstacle (like a gated community).Minimize the time it takes tocalculate the all-in fuel and labor cost for a specific delivery.Maximize the likelihood thatthe quoted price for a delivery reflects its true cost.
These Customer Success Statements are the final, essential bridge. They are the atoms of value. They transform the qualitative insights from our deconstruction into the quantitative, non-negotiable bedrock of our new business model.
We now have all the components. We’ve used Socratic Questioning and the Five Whys to find the true job. We’ve used Job Maps and Customer Success Statements to define the true metrics. We have, in effect, created a “Service Level Agreement” for the outcome itself.
With these hard metrics in hand, we are no longer selling a vague promise. We are making a specific, testable, and contractual commitment. We are finally ready to stop talking about the outcome and start architecting the deal.
I make content like this for a reason. It’s not just to predict the future; it’s to show you how to think about it from first principles. The concepts in this blueprint are hypotheses—powerful starting points. But in the real world, I work with my clients to de-risk this process, turning big ideas into capital-efficient investment decisions, every single time.
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