Ranging over a wide array of interactions, coordination comprises the simple to complex interactions that occur within our daily lives. Many events we encounter ask us to work alone or with a group to achieve a common goal. These goals frequently set the stage for how we find a deeper understanding of underlying principles of coordination. Here, began by focusing on the interaction between two individuals cooperating, and how coupling strength could modulate the connection shared between them. In these initial studies we found that principles and measures of complexity matching applied similarly within and between individuals, and perceptual-motor performance can be facilitated by loose response coupling. We concluded that complexity matching observed between individuals can similarly occur within one individual, suggesting a general principle of interaction at work. When response coupling was absent in the dyadic condition, the degree of complexity matching was significantly reduced. The connection shared between the coupled cooperative agents influenced their overall shared success. Expanding upon this research, we asked investigated coordination within larger groups. To do this, we need to find a situation that fit within coordination but allowed for larger group sizes. A situation that fit these criteria existed in collective foraging. Collective foragers can coordinate and cooperate flexibly over time despite changes to task demands, connectedness, and environmental conditions. The coupling strength linking foragers together often shapes their collective movements. Based on this, we created a scenario where varying degrees of coupling strength bound cooperative agents together as they collectively coordinated their actions in search of hidden targets. We found that loose and flexible coupling among search agents improved collective performance, and that human players improved performance partly by subtle, indirect effects on group interactions. Loose coupling emerged among agents when the rules of interaction were weak enough for agents to act independently or interdependently, while still being strong enough to help hold them together. Movement patterns showed loose coupling enabled collections of agents to self-organize and reorganize into a greater diversity of ad hoc groupings. We continued this work by investigating the link between cooperative interactions among larger groups of agents, coupling strength, and group member effectiveness. By manipulating group member effectiveness, group members performed the search task better than before, but without human intervention, the individual movements of the more-optimal agents continued to lag humans. Based on these results, we successfully instilled a unique agent with a form of memory which helped them to act in more ‘human-like’ ways. Taken together, this dissertation supports a broader narrative where coordination depends on the loose, and flexible alignment of available actions (Glassman, 1973; Kloos & Van Orden, 2009). This adaptive reorganization of behaviors is supported by an exchange of information, dependent upon the connections linking complex networks together (Nordham, Tognoli, Fuchs, & Kelso, 2018; Rigoli, Holman, Spivey, & Kello, 2014; Schloesser, Kello, & Marmelat, 2019; West, Geneston, & Grigolini, 2008). Future work may continue to uncover the underpinnings of interpersonal coordination – with humans, engineered agents, or both.