Small booming hydrocarbon exporting countries are very often challenged to utilize their economic windfall to transform their economies and improve the living conditions for their citizens. Both the transformation of the economy and the improvement of living conditions require the timely and cost effective construction of medium to large scale infrastructure and commercial projects. Such projects bring into focus the construction sector of these countries. This paper analyses the labour shortages in the construction sector of one such country, Trinidad and Tobago, as it forges ahead with the construction of several infrastructure and commercial projects, and proposes strategies to address these shortages. Emphasis is given to Vocational Education and Training (VET) among the proposed strategies.