Don’t say yes, think.
A famous Family Office principal used to say, "I'm not paying you to say yes, but to tell me what you think." It can be assured that he would not take no for an answer, and rightly so.
In a family office, there is no space for politics, prevarication, or bootlicking. By not expressing genuine thoughts, the trust placed in the team would be violated. It is precisely because the boss might not be willing to hear certain things that they must be said. The role is to make positions clear, even in disagreement, and especially in disagreement.
Experience has shown that the boss can hear everything, provided it is communicated politely.