The last decades have been characterised by fundamental changes - a paradigm shift - in organisation theory, management theory and the intellectual constructions through which organisations, managers and individuals working in organisations are understood. The value system of society has been changing, and this has had effects on leadership. Up until recently, the dominant model for leadership has been one which stresses simplicity, order, determinism and linearity. Consequently, today's leaders in the West manifest a moderate tolerance of unequal power distribution in organisations. However, this model has increasingly been coming under fire from conflicting perspectives, for example, new approaches stress complexity, bounded disorder, non-determinism and non-linearity. Under the Eastern and African influences, they also show a shift from the most individualistic approaches to group/team approaches to problem solving. Additionally, strong 'masculine' values, including traits such as aggressiveness, independence and insensitivity to feelings, have been changing moderately to relationship-building, interdependence and concern for others. In the workplace, there appears to be a move away from valuing economic incentives, organisational loyalty and work-related identity and towards valuing more meaningful work, pursuit of leisure, personal identity and self-fulfilment. The modern leader must, hence, be able to recognise value differences and trends among people at work in order to lead them accordingly. This article looks at the plurality of the dilemmas leaders are facing, as we enter the 21st century, because of the multiple realities and perspectives that they have to act out and reflect within the workplace and society.