Anecdotal experiences are discussed relative to efforts assisting property owners with wealth transfers. The author draws from his work in the United States and while on sabbatical in New Zealand. Initially focus was given to the technical aspects and details of asset transfer: organizational structures, ownership of assets, percentages of annual transfer through gifts, etc. Experience led to a redirection of emphasis in dealing with property owners. Efforts were redirected to hard issues of economics (can the farm afford succession) and to soft issues of management, such as mission and vision statements, articulation of values by the property owners ultimately leading to establishment of goals and plans. The transition of wealth, consistent with owner plans, is then executed incorporating business plans, gifting, sales, and bequests all sensitive to tax constraints if any. The most difficult issue often times, is the gathering around the kitchen table to begin the discussion.