There is evidence that agile approaches to information system development can improve product quality and developer productivity. However, successful adoption of these approaches appears to depend on adaptation to specific contexts. This research contributes to a broader goal to understand what it means to “be agile” in the presence of adaptations to the specific context.To pursue our research objectives, we have performed 31 semi-structured recorded and transcribed practitioner interviews from three companies in Lebanon. The interview transcripts were analysed using an approach informed by grounded theory.Agile methods enable learning and improvement through team conversations. Yet, the practitioners in our study shun public self-evaluation, finding it difficult to discuss areas for improvement in public. We also found legacy “top down” management practices that undermine team autonomy and local client companies lack experience of engaging with agile processes. In a more positive vein, we found evidence of rich use of various communications channels to overcome geographical distance.On the one hand, agile methods represent a “northern” idea being propagated to the Global South. And yet, on the other hand, the agile concept of self-organising teams has the potential to be empowering and emancipatory. Post-colonial theory helps us understand the phenomenon of agile tailoring, where development process ceremonies are adapted to suite a specific local context.