They do get it spectacularly wrong at times. I mean hiring Monica Applewhite to tell the RAC about how good jw's are at handling child abuse cases really backfired.
If your advisors - whether financial, legal, property or child abuse - are only interested in keeping their lucrative contracts with you and milking you or if they are jw's keeping their board and lodging and positions of power they will tell you how wonderful you are and agree with you (to your face) when you say you are god's spokesmen, and then you will never get the really needed advice.
Remember when the yearbooks would tell us how the (worldly) M.A.N. press salesmen and installers would tell them "you really are god's people" or it's "obvious god is directing you!" Sucking at the teat of the cash cow the lot of them.