This Special Communication summarizes the key points raised at the Society of Surgical Chairs mentorship panel sessions held at the 2014 and 2015 annual meetings of the society. Highlights of these expert panel discussions include senior chairs' insights into successfully dealing with increasingly complex academic medical organizations and horizontal department management expectations in the context of the arrival of the Millennial Generation into the work force. Three key tenets of effective surgery leadership that arose from these sessions deal with the importance of (1) collaboration and cooperativity, (2) humanized relationships and mentorship, and (3) operational efficiency. Overall, the panel consensus for the future of surgery leadership was optimistic while recognizing that the demands of chairmanship are considerable.