When you talk to potential customers, you could ask any number of things. It can be overwhelming. Loaded questions like “would you buy this?” rarely work because the recipient is worried that an honest answer will hurt your feelings.
I’ve got a couple favourite lines of inquiry which root out some deal-breaking issues and give strong evidence about whether or not your current direction is viable.
If you’re building a better version of something they already have, the most important questions are:
What are they using now? How much does it cost and what do they love and hate about it? How much would those fixes be worth and how big of a pain would it be for them to switch to a new solution?
Where will the money come from? Whose budget is it in, do they spend money on this sort of thing already, and who will need to approve the purchase? Or put another way, who is allowed to kill the purchase? The legal team, tech team, executives, daily users… You can’t make sure everyone is happy if you don’t know who they are.
On the other hand, if your business helps them to do something new, which they couldn’t do before, the key questions are:
What is their workflow? How do they spend their days, what tools do they use, and who do they talk to? Since you’re not just creating a substitute for part of their existing workflow, you’ll have to understand how you fit in and whether they’ll be willing to learn another piece of software, visit another website, etc.
Which are the 3 big problems they’re already trying to solve? If your customers aren’t already annoyed by and trying to fix something, you’re not going to be able to convince them it’s a real problem. You need to find out what they actually care about, not what you think a hypothetical, perfectly rational agent ought to care about.