Find Pain Points That Trigger Action

You're a founder. You have a product idea. Maybe you've even built a prototype.

You've talked to some people. They said things like "that's really interesting" and "I'd definitely use that." You felt great. You kept building.

Then you tried to sell it. Crickets. Or worse: "Love the idea, but not right now."

Here's what happened: you found a pain point that exists. You did not find a pain point that triggers action.

Most founders confuse these two things. They hear someone describe a problem and assume that problem is worth solving. It isn't. Problems are cheap. Everyone has hundreds. The question is whether a problem is painful enough that someone will stop what they're doing, evaluate solutions, make a decision, and pay money to fix it.

That's the difference between a pain point and a buying trigger. One makes people nod. The other makes people buy.

This tactic shows you how to find the second kind.

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Why Current Approaches Fail

The "I assume" approach

You never talk to customers at all. You build based on your own experience or market research reports. This fails because your experience is not representative, and market research describes categories, not individual buying decisions.

The "leading question" approach

You ask prospects "Would you buy a product that does X?" They say yes because it costs them nothing to say yes. You've asked about a hypothetical future. People are terrible at predicting their own future behaviour. They're not lying to hurt you. They're lying because humans are wired to be polite and optimistic.

The "compliment collector" approach

You pitch your idea to friends, family, and LinkedIn connections. They tell you it's brilliant. Of course they do. They like you. They want you to succeed. They're not going to tell you your baby is ugly. This produces false positives that convince you to invest time and money in something nobody will pay for.

The "survey" approach

You send a form to 500 people and get quantitative data. "73% of respondents said they experience this problem." Great. But surveys can't tell you how much that problem costs them, whether they've tried to solve it, or why they haven't succeeded. You get data without depth. You know the problem exists without knowing whether anyone will pay to fix it.

Every one of these approaches produces the same failure: you find problems that exist but don't trigger action.

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The Unlock

Pain that triggers action has four characteristics. If any are missing, the buyer won't move. This is what I call the Pain Intensity Score.

Frequency: How often do they experience this problem? A problem that happens once a year is not urgent. A problem that happens every day creates accumulated frustration that demands a solution.

Severity: How much does this problem actually cost them? Not "it's annoying." Actual cost. Revenue lost. Time wasted. Deals delayed. Employees churned. If they can't quantify the cost, they haven't felt the pain enough to pay to fix it.

Urgency: How quickly do they need to solve this? Is there a deadline, a mandate, a consequence? "We need to fix this before board meeting" is urgency. "We should probably address this at some point" is not.

Willingness to pay: Have they already spent money trying to solve this? If they've paid for alternatives, hired consultants, or allocated budget, you know the pain is real. If they've done nothing, you should ask why.

Score each dimension 0 to 10. A pain that scores below 6 on any dimension is unlikely to trigger a purchase. A pain that scores 8+ on all four is a buying trigger.

Most founders discover their "validated" pain scores 7-8 on severity but 2-3 on urgency. The problem is real. Nobody will act on it.

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The Tactic

The goal of a customer conversation is not to pitch your idea. It is not to get validation. It is to extract the truth about whether a pain is intense enough to trigger action.

You do this by asking questions about the past, not the future. People lie about what they'll do tomorrow. They tell the truth about what they did yesterday.

Here is the 5-Question Sequence:

Question 1: "Walk me through the last time this happened."

This forces specificity. You're not asking if they have a problem. You're asking them to describe a specific instance. When did it happen? What were you doing? What went wrong?

If they can't describe a specific instance, they don't have this problem often enough for it to matter.

Question 2: "What are the implications of that?"

This extracts severity. You're not asking if the problem is bad. You're asking what happens when it occurs. Does it delay revenue? Does it cause rework? Does it frustrate customers? Does it make them look bad to their boss?

If the implications are vague ("it's just annoying"), the pain is not severe enough to trigger action.

Question 3: "What have you tried to solve it?"

This tests commitment. If they've never searched for a solution, they don't care enough. If they've tried three tools and hired a consultant, the pain is real and they're actively in the market.

This question also reveals your competition. Not other products. The workarounds, spreadsheets, and manual processes they're using today.

Question 4: "How much time or money does this cost you?"

This quantifies the pain. Force a number. "Roughly how many hours per week?" or "What's your best estimate of the annual cost?"

If they can't quantify it, they haven't thought about it enough to prioritise it. If they can quantify it instantly, it's top of mind.

Question 5: "Why haven't you solved it yet?"

This is the scary question. The one that could kill your business. Ask it anyway.

The answer tells you everything. "We haven't found a solution that works" means the market is open. "It's not a priority right now" means they won't buy. "We're evaluating options this quarter" means you're talking to an active buyer.

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The Formula

Before your conversation, prepare this template:

PAIN INTENSITY AUDIT

Prospect: [Name, Role, Company]
Date: [Date]

SPECIFIC INSTANCE:
[What happened, when, context]

IMPLICATIONS:
[Business impact they described]

SOLUTIONS TRIED:
[What they've already done]

QUANTIFIED COST:
[Time/money they estimated]

WHY UNSOLVED:
[Their stated reason]

SCORES (0-10):
- Frequency: [Score] | Evidence: [What they said]
- Severity: [Score] | Evidence: [What they said]  
- Urgency: [Score] | Evidence: [What they said]
- Willingness to Pay: [Score] | Evidence: [What they said]

TOTAL PAIN INTENSITY: [Sum/40]

After 5 conversations, write your Validated Pain Statement:

For [specific role] at [specific company type] who experience [specific pain],
the cost is [quantified impact] and they currently solve it by [current solution].
They are actively looking for a solution because [urgency driver].

If you can't fill in every blank with evidence from your conversations, you haven't validated the pain.

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Worked Example

A founder building expense reporting software for finance teams. Here's an actual conversation using the 5-Question Sequence:

Setup: The founder reached a Finance Director at a 200-person SaaS company via a warm intro.

Q1: "Walk me through the last time expense reporting caused a problem."

"Last month. End of quarter close. We had 40 expense reports outstanding. I spent two days chasing people for receipts. One report was missing £8,000 in vendor payments. We couldn't close the books on time. I was in the office until midnight on a Friday."

Q2: "What were the implications of that?"

"Board meeting was Monday. I had to present preliminary numbers with a disclaimer. The CFO was frustrated. It made the whole finance team look disorganised. And honestly, it's not the first time. Happens every quarter."

Q3: "What have you tried to solve it?"

"We use Concur. Hate it. We've looked at Expensify, but migrating is a nightmare. We built a Slack bot reminder system. Still doesn't work. I've considered hiring a dedicated accounts payable person just for this."

Q4: "How much time or money does this cost you?"

"I personally spend about 10 hours per month chasing expenses. My two staff accountants probably spend another 20 hours combined. So 30 hours a month. At an average cost of £50 per hour for the team, that's £1,500 a month in labour. £18,000 a year. Plus the delayed close costs us visibility into cash position."

Q5: "Why haven't you solved it yet?"

"Honestly? It's never been the top priority. There's always something more urgent. But the CFO mentioned it in my last review. He wants it fixed before next fiscal year. So I actually have to do something about it now."

The Pain Intensity Audit:

SCORES (0-10):
- Frequency: 9 | Evidence: "Happens every quarter", monthly chasing
- Severity: 8 | Evidence: £18k/year, board presentation impact
- Urgency: 8 | Evidence: CFO mandate, "before next fiscal year"
- Willingness to Pay: 7 | Evidence: Already paying for Concur, considering hire

TOTAL PAIN INTENSITY: 32/40

The Validated Pain Statement:

"For Finance Directors at 100 to 500 person companies who experience expense report delays at month-end close, the cost is 30+ hours of team time monthly (£18k+ annually) and delayed financial reporting. They currently solve it with inadequate tools (Concur/Expensify) plus manual chasing. They are actively looking for a solution because CFO has mandated improvement before fiscal year end."

This is a buying trigger. This person will purchase a solution.

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Why This Works

People lie about the future because it costs them nothing to be optimistic. "I would definitely buy that" is free to say.

People tell the truth about the past because they're describing what actually happened. They can't lie about the midnight Friday or the £18,000 in labour costs. Those are facts.

The 5-Question Sequence forces past-tense specifics. Each question builds on the last:

• Question 1 establishes that the problem actually occurs
• Question 2 reveals whether the problem has real consequences
• Question 3 shows whether they care enough to have tried solving it
• Question 4 forces them to confront the actual cost
• Question 5 reveals whether they're ready to act

By the time you've asked all five, you know whether you're talking to a buyer or a polite nodder.

The Pain Intensity Score turns qualitative conversation into quantitative assessment. You stop relying on gut feeling ("that call went well") and start measuring actual buying signals.

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Common Failures

Accepting "I would definitely use that" as validation

This is worthless. Rob Fitzpatrick calls it "the world's most deadly fluff" because it sounds so concrete. It isn't. The only validation that matters is past behaviour (they've already tried to solve this) or concrete commitment (they'll pay a deposit, attend a demo, introduce you to the decision-maker).

Asking about the future instead of the past

"Would you use a tool that..." is a hypothetical. "When was the last time you..." is a fact. Ask about facts.

Stopping at the first problem mentioned

Prospects have many problems. The first one they mention is rarely the most painful. Ask "What else?" and "Is that the biggest challenge?" to find the real pain.

Not asking the scary question

If you're afraid to ask "Why haven't you solved it yet?" you're not doing customer discovery. You're collecting compliments. The answer to this question determines whether your business can exist. Ask it.

Talking too much

The customer should talk 80% of the time. Every word you say is a chance to bias the conversation. Ask short questions. Wait. Let them fill the silence.

Interviewing friends

Friends lie because they like you. Interview strangers. Pay for access if you have to. LinkedIn Sales Navigator costs £80 per month. Cold emails work. The truth lives with people who don't care if they hurt your feelings.

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Next Tactic

You've found a real pain. You've validated it with evidence. Now you need to build your ICP around it.

The pain you discovered isn't universal. Specific types of companies, specific roles, specific situations experience it most acutely. That specificity becomes your Ideal Customer Profile.

Read: Define Your ICP in 30 Minutes

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Full methodology: The Forensic Persona Audit