Sometimes pain isn't quite enough

You can never underestimate a customer's capacity to tolerate pain.

Most advice focuses on problem identification and validation. But here's what people miss: pain severity.

Think about your day. There are dozens of things I hate... but tolerate. Like deciding what's for dinner with a teenager and a picky grade-schooler. It's a nightly headache. Would I pay for a solution? Nope. I'll keep tolerating it.

The enterprise is no different. I would argue that our collective faith in Excel to run financial infrastructure proves it.

So what should you do in customer discovery to account for this?

1. Quantify the Pain

Ask: "How much time, money, or effort is this costing you?" If they can't quantify it (or the number is small) it's not severe pain. Push for specifics. Instead of "manual payroll is annoying," dig into consequences: errors, time spent fixing them, financial impact.

2. Understand the Alternatives

Ask: "What are you doing today to solve this?" If they're spending money or significant effort on a workaround, that's promising. But if they're just tolerating it? Might not be severe enough. Sounds like my dinner problem, figure out what might make them switch. You need to be at least 10x better than the status quo.

3. Test Willingness to Pay

Ask: "Would you pay $ to solve this?" Don't be afraid to push. Hesitation means the pain isn't severe enough or your solution isn't compelling enough. Willingness to pay is the clearest indicator of value.

Bonus: Look for Emotional Pain

Sometimes pain isn't financial. A lot of the time it's emotional. Embarrassment from errors? Frustration from inefficiency? Emotional pain drives decisions too, especially in enterprise. If you make someone's life easier or make them look good, you've got a strong value proposition.