Examining the experiences of a sample of Jamaican teachers during that critical first year after professional training, the paper looks closely at their accounts of their classroom management style, and how they balance their own personal beliefs as well as what they learned in college with the reality of the learning environment. Interviews yielded data which suggest that those teachers with classroom experience prior to entering college were more comfortable with a democratic management style than those without this exposure. Also there were those who feared loss of control and a breakdown in discipline and consequently did not favour such an approach. Several other factors emerged as influencing classroom democratization, such as the teacher's physical stature, pressures of the syllabus and examinations, class size, space, teacher image, and pressures from older teachers. The findings pertaining to all the teachers interviewed are presented, with six cases presented in detail.