Excellent BossMan ... there is no question we MUST get this prospect to tell us in their own words what they are thinking ... we want to know - "WHY?"
Did you think of a simpler question, one that gives even more latitude for response? May I suggest you try this next time;
"Why do you feel that way Mr./Ms. Prospect?"
The other responses, like justifications for what their people are good at and what it will cost them to do it versus out sourcing to experts who do it everyday ... how that will be cheaper for them, providing proof of companies that tried it and then had to out source anyway ... all of these things are not wrong, they just come AFTER he/she tells us more about why they feel what they do.
Until that prospect talks, tells us what they think, we are literally shooting BLIND with any response. And that is no way to sell professionally.
Great question Jeff ... real provocative.
Remember that we need the person to tell us what they think first. And OPEN ENDED or OPEN PROBES are the best way to do that. In some cases, when the prospect is talkative, all you need to do is say "Oh!" or "Oh really!"
When they are talking we gather information, recognize objections, uncover opportunities that may be answered by the benefits our product or service.