In a world of unprecedented pandemic turbulence, the role of the digital interface is increasingly growing, with ubiquitous acceptance and integration into business processes and information exchange. This research is intended to evaluate the acceptance of videoconferencing as a form of virtual communication in the construction and construction-related industries by key decision-makers in Australia and New Zealand. Furthermore, this work seeks to explore the influence videoconferencing has on industry collaboration effectiveness, communication openness, relationship advancement, and trust-building. This qualitative enquiry investigates the impact of on-line modes of interaction on communication openness between business decision-makers during face-to-face and on-line interactions. Through a series of 18 in-depth interviews with executive decision makers in Australia and New Zealand and subsequent thematic analysis, findings detail a comparison between the quality of shared knowledge, as operationalized by such parameters as accuracy, usefulness, and timeliness, and the quantity of shared knowledge, by investigating responses to questions such as “am I getting enough information?” from the perspective of business decision-makers. These characteristics directly influence trust-building and substantially contribute to developing long-term healthy relationships. This work features a key insight into the influence of relationship tenure, or whether a relationship is new or mature, as influencing the openness and effectiveness of on-line interactions.