While policies and regulations are essential to guide and promote a City Greening agenda, the detailed application of guidelines often falters due to the dominance and inflexibility of engineering constraints. Adopting a City Greening-first approach encourages our teams to challenge the status quo and define solutions that champion the thoughtful integration of vegetation, open spaces, and water management strategies. This approach enhances biodiversity, mitigates the urban heat island effect, improves air quality, and creates enjoyable public spaces.