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Productivity growth is associated with competitiveness, profitability and sustainability in the construction sector, whereas studies underline that poor supervisory characteristics and training resources are the leading causes of construction productivity loss. This study employs a case study to evaluate the capabilities of construction supervisors to apply planning and management approaches for enhancing the effectiveness of construction operations. A new training programme for construction supervisors was designed using meticulous sequential methods, and 59 construction supervisors were trained and assessed under seven elements of competencies and the relevant learning domains. An assessment guide with varying degrees of descriptions and criteria was accomplished through literature reviews and professional interviews. The study has produced a new generalised guideline that shows the cross-section of what levels of skill/ability can be taken into account in supervisory attributes as a result. Using pertinent statistical evaluations and expert assessments, the reliability of the results, as well as the generalisation of the study’s applications and outcomes, were guaranteed. The study has opened a valve that allows new values of highly practicable supervision features to flow into the site management structures, filling the industry’s knowledge vacuum in the methodical execution of apprenticeships. Though the study’s conclusions/findings are particularly applicable to a developing country's construction environment analogous to the Sri Lankan context, they will have a significant impact on current/future industrial practices in a variety of other countries and rising industries.