Water management practices in cities around the world are faced with growing social and environmental pressures. Unfortunately, the linear “take-make-waste” approach, previously recognized as the most conclusive practice to address water-related issues, has been found to be unsustainable due to its dependence on the limited availability of energy and resources. It is, therefore, necessary to change the current linear approach dominant in most cities across the world to one that utilizes a high degree of reuse and recycling that is known as “One Water”. The goal of this study is to evaluate a series of expert interviews that were conducted with utilities across the US and Canada to gain insights into implementing One Water principles. Interpreting several interviews is the key step to provide water managers with an understanding of the perspective and required actions towards transitions in urban water management. The results indicated that although several pressures were described in the expert interviews responses, climate change was the most frequently described pressure, followed by water quality impairments and population growth. Moreover, it has been identified that the studied cities have implemented several strategies such as green infrastructure, recycled water, desalination, and stormwater management to achieve this holistic approach. The thematic analysis revealed that all cities demonstrated the importance of cultural change to break down silos and support various technological solutions. Further investigations revealed that cities encounter several barriers that inhibit the One Water transition. One of the most frequently discussed barriers was related to financial challenges in most cities, especially in light of the pandemic when substantial cities lost their revenue. In addition to the financial challenges, lack of regulatory process and framework, institutional barriers for expanding One Water strategies, short-term thinking, lack of collaboration, community resistance to change, lack of public support, and water rights were mentioned by participants as the top barriers.