Purple Compass worked with William Osler Health System’s (Osler) corporate planning team to support development of their 2019–2024 Strategic Plan. Our approach was a combination of traditional strategic planning with strategic foresight/futures methods and was integrated into the corporate planning process. This included hosting a Futures Summit with a tabletop session exploring four alternate scenarios of the future health environment over a 10-year horizon. The scenarios provoked dialogue about complexity and uncertainty towards finding common meaning, generated new insights and identified Osler’s preferred future over the long-term in order to align strategic planning efforts.