The shift towards digitalisation has been empowering growth in the construction industry, especially in the past decade. Construction stakeholders are offered myriad benefits by embracing digital advancements to achieve efficiency. However, the exploitation of digital opportunities is bounded by the need for a practitioner skillset that aligns with the digital era, a requirement that has been described as difficult to meet and justified by the low degree of digital literacy among construction employees. This paper reports findings from interviews with 19 leaders and decision makers in the construction sector to reveal the indicators that can predict construction employees’ digital literacy. Such an approach offers a comprehensive exploration of the likelihood of employees’ digital literacy through socially oriented characteristics. Overall, 19 individual characteristics emerged from the thematic analysis and highlight the critical connection between social behaviour and digital literacy. The findings of this paper are timely and important for those businesses assessing their employees’ willingness and maturity with regard to technological change through social and behavioural information. The qualitative approach led to the development of a conceptual framework that can explain the dynamics needed to assess employees’ digital literacy in construction organisations. This study, therefore, reveals the effectiveness of predicting employees’ readiness to shine in the digital era by shedding light on their digital literacy through examinations of individual characteristics in a construction workplace. This paper is among the first to encourage research efforts that take into account the importance of studying social and psychological complexities, which are subject areas that are limited in recent construction literature. As such, it is of value to employers wishing to embed greater digitalisation in their firms, as well as researchers in this domain and policymakers looking to encourage greater digital transformations.