There's this thing in sales and negotiation I call "blind pitching" - throwing out prices and proposals without having any real idea what's going on the other side.

Story time.

A client of mine got a request from an old colleague to do some dev work. They asked him how much he'd charge and he spent hours agonizing over the perfect number.

He landed on $7000. Not too high to scare them away, not too low to make him feel cheap. Classic middle ground thinking. Classic "guesswork".

He literally made that number up. He had no idea what their budget was, what alternatives they were looking at, or even how much value this would bring to their business. He just roughly estimated how long it'd take, multiplied it by the highest hourly he could stomach and threw it out here.

I love you man, but that's how you leave money on the table while also risking to lose the deal completely - at the same time!

For all you knew they had $50k set aside for this. Or maybe they were hoping to get it done for $500. Or perhaps what they really needed was ongoing maintenance which could have been a sweet retainer deal.

I used to do this all the time. We all do. It's deeply ingrained in our culture - this idea that we need to make the perfect offer that just lands and they say yes. Like we're supposed to read minds or something.

The reality is that sales is a conversation, not a shooting range. You need to understand their situation before you can make an offer that makes sense. What are they trying to achieve? What's the real value of solving this problem? What other solutions are they considering?

But we're afraid to ask these questions. We think it's unprofessional or pushy. So we end up playing this silly guessing game instead.

This is a very hard lesson to learn. I still fail to ask enough questions half he time. I still try to have he entire conversation in my head before it happens.

But here's the beauty of the conversational approach - despite what your lizard brain is telling you, it's actually impossible to get rejected or seem unprofessional when you ask honest questions.

That only happens when you guess.

Your move.