Talk2UserPricing is hard. Ask directly and you get bad answers. Skip it and you have no data. The trick is asking about what they pay now, not what they'd hypothetically pay you.
The Core Idea
Ask what they spend today, not what they'd spend tomorrow. What they do beats what they say.
Sample Questions
What They Spend Now
"How much do you spend on this problem today?"
This shows you what they actually pay — whether for tools, workarounds, or time.
Who Controls the Money
"Do you have budget for this, and who controls it?"
Tells you if they can buy on their own or need approval.
What It's Worth
"How much would you pay to make this problem go away?"
Direct, but useful when the problem is clear and painful.
More Questions
"What alternatives have you tried, and what did they cost?"
"How much time do you spend on this each week? What's that time worth?"
"What would you have to give up to pay for a solution?"
"When you've bought tools like this before, who was involved in the decision?"
What Not to Do
- •Don't throw out a price before asking — it biases everything.
- •Don't ask "Would you pay $X?" — they'll say yes to be nice.
- •Don't rely on one conversation — you need multiple data points.
Key Takeaway
Ask what they spend now, who controls the budget, and what alternatives cost. Don't throw out a number first. Use multiple conversations — no single answer is enough.