El Mahdi
Muad'Dib of the Anauroch
I'd like to strike up an Ocean's Eleven style vibe for this, where a direct assault would probably going to end badly for them but casing the joint first would reveal a couple possible security flaws the could exploit.
I don't have anything on what elements to use to give it the Ocean's Eleven feel you want, but I do have an idea on how to discourage them from a direct assault.
I remember taking a tour of the chateau at Carcassonne once. Our tour guide pointed out how the construction of the manor/keep aided in its defense - even after enemies may have made it into the manor. One such example was the direction that stairs curved, giving an advantage to defenders (attackers fighting up the stairs, attackers which were likely right handed as most people are, would find that a clockwise curve of the stairs meant they had the wall on the inside of the turn in the way of their sword arm, while the defenders above them could swing unimpeded - not to mention that defenders had the higher ground).
Maybe one of the party's characters - probably a fighter - would understand and express to the group how the very design of the manor gives the defenders a very real home-field advantage, imposing disadvantage on the party in many areas of the keep and giving advantage to defenders. If the players know they will almost always have disadvantage imposed on them in a fight, they may do everything they can to avoid that sort of approach.
Also, calling the chief-of-staff something like steward, castellan, or seneschal may be more flavorful and setting appropriate.