Managerial coaching has attracted much attention over the last decades and two models have emerged in the literature: the behavioral and the skills model. Both of them have been criticized and the literature is lacking empirical research on the measurement of managerial coaching, its impact on organizational outcomes, and on how it can be developed through training programs. In this article we try to fill these gaps with a first study describing the initial validation of a new instrument for measuring managerial coaching behaviors/skills - The Managerial Coaching Assessment System (MCAS), and a second study testing the effectiveness of a newly developed program for enhancing managerial coaching - The Rational Managerial Coaching Program (rMCP). The MCAS is a multi-rater instrument, allowing for ratings from managers (self-report), employees (other-report) and external observers (observational). In study 1 (N=94) we found the MCAS to have adequate psychometric properties (Cronbach's alphas between .72 and .93 for the three versions) and to be a strong predictor for performance over a six months period, r(17)=.68, p=.003. We obtained a one factor structure for the self- and other-report versions and a two factors structure for the observational version. In study 2 (N=22), results show that rMCP is effective in increasing coaching abilities reported by middle-level managers, t(19)=-2.75, p=.031, and by external observers, t(17)=-2.47, p=.024. We also found an increase in managerial rational attitudes, t(21)=-2.22, p=.037, and a decrease in irrational attitudes t(21)=4.59, p<.001. Implications and limitations for the development and preliminary validation of MCAS and rMCP are discussed.