Many motor skills, such as typing, consist of articulating simple movements into novel sequences that are executed faster and smoother with practice. Dynamics of re-organization of these movement sequences with multi-session training and its dependence on the amount of self-regulation of pace during training is not yet fully understood. In this study, participants practiced a sequence of key presses. Training sessions consisted of either externally (Cued) or self-initiated (Uncued) training. Long-term improvements in performance speed were mainly due to reducing gaps between finger movements in both groups, but Uncued training induced higher gains. The underlying kinematic strategies producing these changes and the representation of the trained sequence differed significantly across subjects, although net gains in speed were similar. The differences in long-term memory due to the type of training and the variation in strategies between subjects, suggest that the different neural mechanisms may subserve the improvements observed in overall performance.