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There is a common perception that, while there may be some ‘teething’ problems experienced during the initial transition to agile, people are much happier, engaged and ultimately more productive in these environments. This study shows that this belief may not always hold true, identifying many serious ‘people’ challenges experienced by 17 large multinational organisations, all using agile for more than three years. The cases provide an interesting insight in that they involve cases where agile was implemented in a top-down manner across the organisations or at least across business units. This is in contrast to most accounts of agile which involve voluntary, bottom up adoption on small co-located teams developing systems deemed to be suitable for agile development. The people issues uncovered include a broad range of problems from recruitment of agile staff, to training, motivation and performance evaluation among others. The paper will conclude with a set of actionable recommendations as to how organisations can overcome these challenges, based on the better practices uncovered in the cases studied.