Founders know they're supposed to ask customers what they'd pay. Almost none of them ask it well, because the natural way to phrase the question anchors the prospect's answer before they've said a word.
Why the obvious phrasing fails
'Would you pay $50 a month for this?' is not a pricing question. It's a yes-or-no question that hands the prospect a number to react to instead of a number to generate themselves. Most people will say yes to almost any reasonable-sounding figure just to be agreeable, which is why this phrasing produces useless data.
The opening line that works
Say: 'If you had to pay to keep using this starting next month, what would feel like a fair price to you?' Then stop talking. Do not offer a range. Do not say 'somewhere between X and Y.' The silence after the question is doing the work; most founders break it too early and hand the prospect an anchor by accident.
When they flip the question back on you
Prospects often respond with 'well, what do you normally charge?' Resist answering directly. Try: 'I'd rather hear what this would be worth to you first, since that tells me more than any list price would.' If they push again, give a wide, deliberately vague range rather than a specific number, and immediately redirect back to their side: 'Somewhere in that range, depending on the value, but you're closer to knowing what that's worth to you than I am.'
Handling 'that's too expensive' live
When the objection comes after you've shared a real price, don't immediately discount. Ask: 'Too expensive relative to what you'd get from it, or too expensive relative to what you expected to see on this call?' The first answer is a value conversation you can have. The second is a positioning problem you should fix before your next call, not a signal to cut the price for this one.
Turning five calls into a decision
Run this exact script on five real conversations before setting a public price. Write down the raw numbers people volunteer, not your interpretation of them. The spread you see across five honest answers is more useful than any competitor's pricing page, because it came from the actual people deciding whether to pay you.