Make It Clear

The Pain Interview

Before you pitch anything, find out what the problem is actually costing them — and whether that number is worth solving.

Pitching before I knew there was a problem

I used to open sales conversations by talking about what I did. Marketing, messaging, strategy — the whole range. It felt honest. It also meant I was pitching before I knew whether the person in front of me had a problem worth solving at all, let alone at what price.

That’s backwards. The pitch should come after the pain is confirmed, not before.

A real pain isn’t a complaint. It’s a problem someone is already actively trying to solve — already losing sleep, money, or time over — whether or not you show up. You find it by asking, not by guessing: What have you already tried? What did it cost you when it didn’t work? What happens if this is still true in six months?

The size of the pain, not the size of your pitch, decides what someone is willing to pay.

Finding the real number

The number that comes out of that conversation isn’t fixed. Sometimes the honest answer is a $1,000 problem — annoying, but not urgent. Sometimes it’s $5,000, or $10,000, or a $50,000 problem the person has been quietly avoiding for a year because nobody asked the right question. The interview doesn’t assume a price. It finds one, by finding out what not solving this is actually costing them.

Most consultants skip this and go straight to describing their process. The process doesn’t matter yet. What matters is whether the problem is big enough, and urgent enough, that the person would rather pay to fix it than keep living with it — at whatever price that turns out to be.

If the answers stay vague — “it’d be nice to fix” instead of a real number — you don’t have a pain worth pitching yet. You have a someday problem. Both are fine to know before you build a pitch around the wrong one.

Try this

On your next discovery call, ask what the problem has already cost them this year. Let their number decide the offer, not the other way around.

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