Godin makes the distinction between selling to strangers and selling to friends, saying that whom you’re targeting makes a huge difference in how you design and deliver your message. Agreed. You do have a much lower “hurdle” in targeting your friends, because they already know you and trust you. Plus, we all like doing business with people we know. But as Godin points out, you probably only have one free pass (in which your friend gives you the benefit of the doubt) to do it right.

I don’t think many people get it right. And I think it’s even harder to sell to your women friends.

I see people messing this up on Twitter and Facebook all the time — the incessant stream of stranger-oriented business propositions and opportunities passing by my eyes each day is mind-boggling. And while I wouldn’t exactly put Twitter followers in the same category as friends (except for a handful, at least in my case), I think that there is an art to it that can work across many platforms.

To Godin’s tips I’d add the following:

• Remember that the relationship comes first. You may be excited, ambitious and ready for rocketing growth, but keep in mind that your female friendships are multi-faceted. You can’t talk business all the time. That’d be boring, and your social invitations will dwindle as a result. Keep on being a great friend, listening and asking questions about what’s happening in her life.
• Instead of an all-out sales pitch when you meet for coffee, plant subtle seeds. If — and only if — an opportunity arises in your conversation to mention something (anything) related to your business, then by all means do so. But limit yourself. If your friend doesn’t turn it around and ask a question related to your business, then leave it for another day. The seeds you’ve sown are likely to sprout when you least expect it.
• If you’re in a business that’s built on selling directly to friends (i.e. Pampered Chef, Arbonne, Avon, etc.), tread carefully. There are boatloads of people who are leery of this business model — myself included. But I also respect that millions of people make a living this way. In my opinion, the trick is to be transparent, first and foremost. If you’re putting together a “makeover party” designed to interest your friends in buying some makeup, please do us all a favor and say so. Don’t tell me you’re “just getting some girls together” and want me to join you. When I find out later that it’s a business thing, I’ll be even less receptive to buying from you than I already was. (Gee, can you tell I’ve had this very experience? But I’m not bitter. I am NOT!)
• Craft your copy with your girlfriends in mind. Say you’re putting together an email for friends and family, letting them in on an unbelievable special offer. I’d recommend a super-honest, even self-deprecatory approach in how you write it. So instead of “Act now on this limited time offer for family & friends!!!!!!”, I’d tone it WAY down and say something like, “Hi, you guys. You’d have to be living under a rock to not know that I sell XYZ Product for a living. And I want to thank you from the bottom of my heart for your love and support on this from the beginning. It’s wonderful to know that my friends care about me enough to consider buying from me! Here’s a little promotion I put together just for you guys — but I don’t want you to feel ANY pressure to buy anything. It’s just there for you to use if you were already planning to purchase, okay? Thanks for your time… I love you all and look forward to catching up soon!”

How do you feel about your friends selling to you? How do you handle this delicate balance? What tips could you add to my list? I’d love to hear from you!