It has been highlighted that a lot of our political leaders and various CEO were all a part of some form of student leadership through their sojourn at the U.W.I. This factors has always been an area for higher education institutions, it is also important to determine how students perceive the leadership development programs from which they are meant to benefit. The study is grounded in the Kolbs, 2015 Experimental learning theory. This posits that we all have the ability to become a leader with different experiences and these experiences impact how we deal with challenges and opportunities to become who we are as professionals and leaders. The researchers embarked on an exploratory qualitative assessment where they utilized past students who were once enrolled in the guild to facilitate interviews. The study used a phenomenological methodological approach in assessing the experiences of these students and assessing these various factors with regard to their personal development.