Most small business owners who want to get into email marketing start off by exporting their Microsoft Outlook Address Book. Makes sense, since that’s where all your email happens.

But there’s a right way to do this, and a very, very very wrong way to do this…

If you just export your entire Address Book and then send those recipients an email newsletter, you will get reported for spam, and you could get your entire company blacklisted.

That’s because your Address Book has:

• People who never opted-in for email marketing
• Contacts at places you bought stuff from (Amazon, eBay, etc)
• People you corresponded with 5 years ago, who have nothing to do with your business (like your ISP tech support)
• Here’s a real life example of this happening to a MailChimp customer.

So what you need to do is categorize your contacts before you export them from your Outlook Address Book. Suggestions:

• People that have opted-in to email marketing from me
• Customers that need emails from me (updates, receipts, etc)
• Customers that might like to hear from me (so they need an introductory campaign)
• Prospects or “targets” that I think would find my company relevant (send these people personal, one-to-one messages inviting them to join your list).

But have you ever actually tried to do that? It’s a huge pain. I’m not an Outlook user, but I know Outlook’s Address Book was not made for segmented exports. Then again, neither is Apple’s Address Book.

Luckily, the folks at ClearContext have a pretty nifty plugin for Outlook. Basically, it scans the messages in your email inbox folders (not your Address Book), and lets you export from there. They’ve even got a patent-pending algorithm that helps determine contacts “who are most important to me” by looking at your conversation history and frequency. In theory, this could lead to smarter list exports, and fewer “address book dumps.” Smart.