Retailers today are being increasingly characterised as winners or losers given rapidly changing customer needs and market conditions. Many senior teams have been left exposed by the pace of this change. Too often, they have failed to recognise the need for an accelerated change in team structures. It can be a painful, personal realisation for all of us that the experiences on which we have built our careers are not as relevant today and for the future. Today’s executives not only require much broader functional experience but a proven track record of disruption and risk taking, preferably across diverse international markets. This report highlights six of the most interesting talent dilemmas and challenges facing retail CEOs and Boards today.