Digital transformation is a daunting process for many business leaders, who sometimes find themselves in unfamiliar territory. This challenge is particularly prominent for resource stretched and multi skilled small and medium sized enterprises (SMEs). This paper provides a context for this on-going discussion, and drivers for transformation will be discussed together with the challenges business leaders are currently facing. Following this, we argue that a digital business can be viewed as an information system (IS) with six common subsystems; people, data, hardware, software, process and communication, that must interconnect effectively. Finally HINGE the project planning approach is introduced and how twelve knowledge transfer partnerships informed this approach. The paper highlights that digital transformation is becoming a necessity and offers a phased approach that enables business leaders to construct a systematic project plan that enables their enterprise to reach new levels of digital maturity in a holistic and meaningful way.