Humans and machines are increasingly reliant upon each other in complex environments and military operations. The near future suggests human understanding of machine counterparts is a required, paradigmatic element. Knowing how to engineer and design for these environments is challenging. The complexity between levels of automation, human information processing, and function allocation authority issues in an adaptive system make it unlikely to find a “one-size-fits-all” approach. There may still be general strategies for engineering in these cases; for example, collaborating and coordinating are familiar requirements of all human team activities, and extend to human-automation teaming. Here, we outline what we believe is one so-called “design pattern” for working agreements. We use the loose structure of prior software design patterns to organize our thoughts on why working agreements are necessary, where and how they are applicable, what instantiating them requires, and how to measure their effectiveness. By choosing the design pattern structure, we end up carefully describing what might work best and what the limits are toward improving human-machine teaming.