Early-stage drainage design prioritizes speed, using simplified assumptions to test options quickly. However, challenges such as combined sewer overflows (CSOs), flooding, biodiversity loss, and wider community outcomes are increasingly interconnected and require a more systems-based approach that extends beyond the traditional boundaries of the water sector. This session explores how connected digital workflows can support the identification, design, and validation of sustainable drainage interventions that deliver multiple benefits. Using an anonymized case study, attendees will see how opportunities can be rapidly explored through parametric site-design workflows in Civil 3D and InfoDrainage, then assessed through system-scale modelling in InfoWorks ICM to understand impacts on flood risk and CSO frequency, volume, and timing. The session focuses on balancing speed, rigour, and confidence in decision-making, helping practitioners understand how technology, systems thinking, and proportionate modelling can support more resilient and integrated outcomes for communities and the environment.