You're taking the conversation out of context.
Chris is not advocating harming the client with his "wing it" comment.
Rather, he is advocating that the agent take action versus experiencing paralysis by analysis, waiting for the "perfect time" when everything about the product sold is known.
Here's the truth.
You're NEVER going to know EVERYTHING about your product, prior to actually SELLING it "live" to real people.
And virtually ALL successes in life "wing it" to some degree, as actual "in-the-trenches" experience is the TRUE instructor from which we learn.
I agree with Dave - I listened to that interview a few weeks back - CW was not saying to just wing it when it comes to the important things like advice, etc.
His point was, if you don't take the shot, you'll never make the basket. The OP is an ***.