With the rapid advancement of technology, older adults are falling further behind and thus contributing to the growing “grey” digital divide. Information and Communication Technology (ICT) is well documented to reduce feelings of social isolation and loneliness in older adults; however, the most effective way to teach technology skills in these populations is still debated. To investigate the most effective and efficient way to teach technology skills to older adults, one participant aged 72 years old was recruited to learn three iPad-based tasks: sending an email, downloading an application from the AppStore, and video calling (FaceTime). These tasks were taught using techniques based in Applied Behaviour Analysis (ABA). The effects of text-based prompts and video modelling with accompanying picture prompts on skill acquisition were assessed via a three-phase alternating treatment experimental design with baseline probes and a final best intervention phase. Results show that video modelling with accompanying picture prompts was more effective than text-based prompts for technology-based skill acquisition in older adults. Potential limitations of the present study and future research are discussed.