Today’s problems across domains like research, engineering, and public policy are challenging, complex, and often ill-defined. In lieu of these challenges, workplaces are becoming increasingly complex socio-technical ecosystems, where social (e.g., planning and collaboration meetings with experts and peers) and technical (e.g., a company’s onboarding guide) resources are woven into networks that individuals navigate through streamlined work processes (e.g., planning practices to encourage iteration). However, using these resources well is often challenging. People struggle with constantly assessing their project needs and prioritizing work in ways that effectively leverage a networked organization’s various resources. Given these challenges, my work asks: _How might we design better planning tools that account for the fluid nature of complex work in socio-technical workspaces? _To address this, we develop and study Planning Orchestration Tools, a system that extends existing planning tools by orchestrating planning activities throughout a work cycle.