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.