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I've never ever ever seen a multi-one-line post or letter or a software program trance me into buying what they're selling.
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I'm into tech as well, and seen how poorly the human factors are handled. It's really not a technology issue, but a world view poor on human factors and human insights at fault.
So yes, this one might not be the answer. However, it's probably something which needs to be encouraged.
I would rank this general concept at the same level of maturity as sales letters were roughly one hundred years ago. I'm not sure what version two is like, but it's probably going to be more interesting around version five or so.
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Feedback is good but it's better when it's directed not freewheeling let them say whatever they want. i.e. Get them to say yes.
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You're putting words into my mouth. Didn't say anything about letting the conversation stray all over the place. And, for a program it would be pretty close to impossible, barring an artificial intelligence breakthrough.
I know face-to-face pros. I've observed them on sales calls. They dialog, but maintain control of the dialog.
The real point is, this would be best looked at as a form unto itself -- unlike a long form single page sales letter. And a rather young form, with all that implies.
Plenty of high tech widgets and fads do terrible things to response. Given some caution, and testing, this (or something along the same idea) could be worth looking into.