The Unique Boss/Assistant Relationship Is Unique to Its Own

I’ve heard about the following dilemma in one form or another many times, usually in a private conversation in the corners of one of my seminars. It captures the essence of the personal and nuanced relationship of trust that can exist only between an assistant and boss:

Dear Nan:

I am the executive assistant for Mr. D, the CEO of a successful company with about 400 employees. Mr. D is a well-respected businessman within our organization and the community. For the past 15 years, we have developed a professional working relationship based on trust and mutual respect. My job description includes responsibilities of a personal nature: for example, handling his personal financial records, appointment calendar, personal and professional travel plans, along with duties related to his commitments to outside boards and trade and civic associations.

Mr. D told me in confidence about six months ago that he was planning to divorce his wife. He did not even have to ask me not to share this information with anyone else; he knows our professional relationship would preclude such an action.

I have become concerned, however. Within the scope of my assistant responsibilities, I have assisted him in the transfer of titles of ownership of several major assets. I have also helped him open new bank accounts, and set up trust accounts for his children and several other people with whom I am not familiar. I’ve even arranged a storage locker ...

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