From early jazz to current sub-styles, the key component, improvisation, is thought to also be important to the coaching process. Improvisation in jazz can be conceptually linked to the dynamic, interactional relationships such as those found in coaching. Using jazz history, this conceptual paper investigates how jazz improvisation may inform coaches and coachees in individual, group, or organizational coaching programs. Several propositions are provided through the relationships between the number of coachees, decision-making speed, group size, level of pre-arrangement, and improvisation. Utilizing the information provided in this paper may prove fruitful for coaches seeking coachee performance through spontaneous creativity.