Awhile back Boost Media published a Win of The Week, basically saying that as an PPC copywriter, you have to make sure you place yourself in the prospect’s emotional state and life situation, rather than just relying on your own gut instinct. And that advice continues to hold true, as this recent contest attests: So, if you’re like me, you might wonder why the losing ad lost. After all, the losing ad took the “Free and Online” appeals and put them into the headline. It also specified that the free version wasn’t just a trial — it was free forever for 3 users or less. Enter the “you are not your prospect” factor. First, having serious CRM software available on the App Store might not be very reassuring to non-Apple/Mac sales people. They’re looking for serious business software, not some stupid iPhone “app.” Second, the “3 Users” bit may have confused more than helped. If you have a sales and support team of a half-dozen or more people, a free trial sounds a lot better than 3 free users, doesn’t it? And last, there’s the buoyant benefit of the winning ad: “Discover How to Boost Your Sales.” If you’re just getting into CRM, you might value implementation help and instruction as much as the actual software service itself. So not only does featuring a benefit of “Boost Your Sales” help, but couching it so as to imply that the service will help you to “discover” how to achieve that benefit becomes even more powerful. So, if you’re a more technically and software minded, Mac-loving kind of guy (or gal) then the losing ad might appear more persuasive and substantive. But if you’re a late adopting, PC-using sales manager, then the winning ad would definitely be the one to win you over, as it was. Bottom Line: You are NOT your prospect. Which means that You must conscious endeavor to think like you prospect — to put yourself in her (or his) shoes. And it also means you should test your ads, because empathy aint easy, or assured, and the curse of knowledge can still bite you, even when you’re trying to avoid and overcome it.