Who will pay, not just praise?
“I would use that” is a useful opening to a conversation, not a sales forecast. Before committing more money or time, find out who has the problem, how they deal with it now and what would make them change. This matters whether you want a profitable owner-run business, a larger company or an acquisition.
Ask about the last time, not an imagined future
Start with a specific occasion when the problem occurred. What triggered it? Who did the work? What did the workaround cost in money, time or missed opportunities? Ask to see the process where appropriate, without requesting confidential customer information. A recent example is easier to assess than a general statement that something is frustrating.
Avoid presenting your solution before you understand the current behaviour. People can be generous about an idea and still have no reason to buy it. Record their words separately from your interpretation, including evidence that the problem is infrequent or already solved well enough.
Find the person who can say yes
The user, budget holder and final approver may be different people. Map the buying process: who requests the change, who pays, who can block it and when a decision could realistically happen. For a small consumer purchase those roles may be one person; for a business contract they may involve several teams.
Ask what a switch would require. Training, procurement, data migration and the risk of disruption can outweigh a lower price. A useful offer addresses those costs rather than assuming dissatisfaction automatically creates demand.
Test a commitment you can honour
Choose a next step that matches the uncertainty. A conversation with the budget holder tests access. An agreed pilot with a defined price, scope and review date tests more than an email sign-up. Payment is stronger evidence of willingness to pay, but one friendly buyer does not prove repeatable demand.
Be explicit about what exists, what is experimental and any refund or cancellation terms. Never take money for a promise you cannot responsibly deliver. If you are assessing an existing business, compare customer conversations with actual transactions, renewals and customer concentration rather than relying on the seller’s account alone.
A next step you can take
- Write one sentence naming the buyer, problem and current alternative.
- List what you have observed, what someone has said and what you are assuming.
- Agree one concrete next commitment and a date to review it. Use the Buyer gate self-check in The Method to identify remaining gaps.
Explore the Pentacorn Method or see how these questions fit into the eight-week programme.