The First Sale Is the Hardest One to Ask For

You know that you are offering good value.

You've thought about it for months. Maybe even years. You refined it, questioned it, and refined it again. You thought about how to explain it. In your mind, it all went well.

And then you finally had someone in front of you that you could help. Maybe at a networking event. Maybe you were meeting for coffee.

And you froze.

You didn't freeze because you didn't believe in what you are offering. You truly know that you are there to help them.

You froze because asking someone to pay you for helping them feels different than anything you've done before. It feels presumptuous. Maybe a little vulnerable, because you might feel like you are asking them to validate YOU in addition to your offer.

That isn't really a sales problem. It's a people problem. A problem that is common for us NICE guys/gals.

This Is What's Happening

For most of your career, someone else set the price. Someone else did the asking. You showed up, you delivered, you got paid. The transaction happened somewhere above your head and you never had to look anyone in the eye and say: this is what I'm worth.

Now, as an entrepreneur, you do.

And every doubt you've ever had about yourself shows up in this conversation. Is it, or am I, good enough? Is this too much to ask? What if they say no? What if they say yes and then realize that it isn't like I promised?

None of that is about sales. All of that is about fear.

The good news is, fear means you care. And people who care tend to deliver.

The Other Thing That Is Happening

You're probably trying to sell before you've actually helped them.

Think about the last time you bought something from someone you trusted completely. Chances are, that person had already shown up for you in some way. They'd answered a question, they'd shared something useful, and they'd made you feel like they actually understood your situation.

You didn't feel sold to. You felt seen, because they helped you already.

That's the whole game.

The N.I.C.E. process isn't a closing technique. It's a way of helping someone understand their own problem more clearly. When you do it well, you're not asking them to buy. You're asking them if they'd like help with something they've already told you is keeping them up at night.

That's a whole lot easier. That conversation is easy and comfortable... for both you and them.

Here Is What You Can Do

The first sale isn't about asking someone to pay you.

It's simply about finding someone with a problem, caring enough to understand it completely, and then asking if they'd like your help solving it.

That's it.

No pitch. No closing technique. No pretending to be someone you're not.

Just a good conversation with a person who actually needs what you do.

You've had harder conversations than that. You know it too.

Start There. Just One.

Not a hundred cold calls. Not a thousand emails. Not a funnel or a campaign or a launch strategy.

One person. Someone you already know, or someone you've already started a conversation with. Someone who has the problem you solve.

Ask them one question about it. Then listen. Then another question. And another.

The sale will take care of itself.

If you've had the experience above, I'd love to hear about it. Tell me where you're stuck. That's exactly what I'm here for, and I love to do it.

This article first appeared in my LinkedIn newsletter, Approachable Entrepreneurship.

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That first question gets you started. How to Sell When You Hate to Sell walks through the right types of questions and the order they go in, so the first sale (and every one after it) feels like helping instead of asking.

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Keep reading: Stop Avoiding the Sales Conversation