Almost three decades after the rise of sustainable development as a grand vision, we are facing an implementation deficit in practice (Holden, Linnerud, & Banister, 2014; Newton, 2012).Worldwide, in critical sectors such as water, energy and transport, investments in conventional infrastructure predominate, and the adoption of sustainable alternatives often remains too slow (Negro, Alkemade, & Hekkert, 2012; Rijke, Farrelly, Brown, & Zevenbergen, 2013; Walsh, Glendinning, Castán-Broto, Dewberry, & Powell, 2015). Scholars agree that the shift in infrastructure delivery in today’s cities toward sustainable solutions would be a radical change (Pickett et al., 2013; Truffer, Störmer, Maurer, & Ruef, 2010), requiring cumulative capacities built into strategic planning processes. Currently, a range of impediments across different sectoral and geographic contexts tend to delay, divert or stop the desired transformation (Brown & Farrelly, 2009; Negro et al., 2012). Strategic planning literature often refer to those impediments as barriers (e.g. Ferguson, Brown, & Deletic, 2013; Hunt & Rogers, 2005). Innovation literature refer to them as systemic problems (e.g. Wieczorek & Hekkert, 2012) or systemic failures (e.g. Klein Woolthuis, Lankhuizen, & Gilsing, 2005). They include a range of political, economic, social, institutional and technological issues, such as: lack of political will, insufficient capital resources, limited community engagement, fragmented institutional frameworks and technological failures (Brown & Farrelly, 2009; Klein Woolthuis et al., 2005). While there have been some academic attempts to categorize the impediments to the adoption and successful implementation of sustainable infrastructure solutions, not much has been said about how to identify them systematically in a practical context (Wieczorek & Hekkert, ۲۰۱۲). More importantly, it is not well understood how strategic planning methodologies can incorporate an explicit consideration of those impediments, and assist planners and decision makers in designing the required resolution strategies.