Perhaps the greatest challenge facing the cost estimating community over the next decade is the loss of knowledge and experience of highly experienced estimators as a high percentage of them are retiring and a shortage of qualified cost estimators is evident in the construction industry. This study identified 23 core estimating competencies classified into skills, knowledge, and personal attributes and also identified the gaps between the current and desired level of the estimating competencies. In total, 228 completed questionnaires were collected through the Construction Industry Institute (CII) member companies, and the Association for the Advancement of Cost Engineering -International (AACE-I) and American Society of Professional Estimators (ASPE) workshops. A criticality matrix was developed to prioritize competencies based on the combined effects of the level of importance of each competency and its associated gap. The factor analysis technique has been applied to investigate the correlation effects of the 23 estimating competencies. An implementation tool which assesses the current level of competencies of an estimator or an estimating team and recommends appropriate training tools has also been developed. The findings of this study will help engineering and construction companies design and develop appropriate educational and training programs to enhance estimating functions.