Have you ever said, “Doesn't hurt to ask” and meant it? Do you really think that's true?

Of course, it hurts to ask. What a stupid thing to say. It can hurt a lots to ask. If you do it:

• in the wrong way
• at the wrong time
• to the wrong person

Whoever said it doesn't hurt to ask has never been turned down for a date. They've never made an offer someone could refuse. So if this is you, let me tell you: it hurts to ask.

That's what makes asking so scary and so risky. There is something we can lose: our honor, our self-respect, even relationship with that person. It's supposed to hurt to ask; that's what makes permission so valuable.

Okay, so what does this mean for us bloggers and artists and entrepreneurs? A few things:

1. Learn to ask in the right way. In other words, get permission. If want to sell digital products, ask people first to subscribe to your email list. Start a conversation before you start pitching. Get people to download a free mp3 sampler before you ask them to buy the whole album. This is about attention. Don't demand or expect it; earn it.
2. Discern the right and wrong times to ask. In other words, use your brain. Pay attention. Are you making people comfortable? Are you affirming their struggles? Build a relationship before you start asking for things. Treat every meeting, every phone call, every email as an opportunity. And don't take a single one for granted.
3. Don't ask the wrong person. Who is that, you say? I'll tell you who: a perfect stranger. We don't pay attention to people we don't know or trust. Invest in the relationship, and save the asking for later. Sometimes you only have to wait an hour, but the reward is worth it (like selling a product after you speak at a conference, for example). You know you're asking the right people and when they're coming to you.

This isn't about selling products or getting published, by the way. It's about people and how we're all wired. Everything comes down to trust. Whether you're a plumber or a painter or somebody who works in a cubicle, you have to get people to trust you.

So how do we do this without becoming sleazy, multi-level marketers? Easy. Do what all humans do: build a relationship. Use every interaction to give someone (i.e. a customer, a friend, a fan) another reason to believe you, to want to listen.

Do that — and never violate the understood permission it entails — and you'll be set.

And if that doesn't work, spend time helping someone and then don't ask for anything in return. Serve your way into influence. When the moment is right, you can ask. But maybe then, you won't have to.

What do you think? Does it hurt to ask? What are some examples? Share in the comments.