In an attempt to efficiently – both financially and logistically – bolster their compliance programs, many private equity sponsors are asking their general counsels (GCs) to serve simultaneously as their chief compliance officers (CCOs). There is a proven path forward for one person to perform both roles, but it requires acknowledging and navigating distinct challenges that can arise along the way. Failure to put a so-called “dual-hatted” GC/CCO in an optimal position to succeed can produce a slew of unintended consequences, ranging from the loss of attorney-client privilege in certain contexts to SEC liability for inadequate compliance practices. This two-part series presents the full range of considerations for fund managers that are considering having a dual-hatted GC/CCO in order to assist them in preempting issues it may raise. This second article details some inherent challenges with having the GC and CCO roles occupied by a single person, along with five practical steps for solving them. The first article described the typical duties of a GC and CCO, as well as benefits of having one person perform both roles. See “Simon Lorne, Chief Legal Officer of Millennium Management LLC, Discusses the Evolving Roles, Challenges and Risks Faced by Fund Manager General Counsels and Chief Compliance Officers” (Sep. 26, 2013); as well as our two-part series on the risks and expanding role GCs and CCOs face in a changing E.U. marketing environment: Part One (Dec. 10, 2015); and Part Two (Dec. 17, 2015).