Managers are frequently offered conflicting advice to increase the organisation‟s ability to meet its goals; grant employees autonomy, which may lead to self-management and empowerment or alternatively, exercise control which may enable managers to retain a firm and organised workforce. Management are constantly challenged with this complex dilemma. This research will focus on the key factors that influence the various combinations of autonomy and control and their respective outcomes. To this end, qualitative research with an exploratory design was conducted, as this approach has the potential to delve deep into this quandary. Consequently, in-depth interviews with 16 leading management and HR experts were held to uncover their unique insights regarding this dilemma. The rich data that was unearthed was analysed using content and frequency analysis. The empirical findings of this research found that combinations of autonomy and control can certainly co-exist in an ever-changing fashion. Management are able to create environments with high levels of autonomy whilst simultaneously retaining high levels of monitoring and oversight when the management control is subtle and indirect. This approach will solve the dilemma under review by neutralising employee‟s negative resistance commonly associated with direct control. A total of seventeen factors were identified that could influence the different levels of autonomy and control in organisations.