This article will look at the hurdles of dealing with ambiguity and the wicked problems that organizations are struggling with, by providing key insights from a one year team coaching program that the author had the opportunity to deliver in a Romanian entrepreneurial organization. Based on the actual methods used and highlighting the findings and impact of the program, we will reflect on how ambiguity manifests in organizational settings and how wicked problems can be defined. The methods employed are within the range of complexity science and are holistic approaches to systemic interventions within organizations that combine soft systems methodology, paradoxical theory of change, complex responsive processes approach with important concepts from systems thinking such as archetypes, feedback loops and modeling. One of the key objectives of the article is to reunite different academic approaches and link them to a case study as a way of adding value to these approaches and to reiterate that research needs, to find its rightful place in the practitioners’ toolkit and have a more meaningful and direct impact on the real struggles that business is faced with. The author’s expertize in systemic interventions is based on extensive practitioner experience, having been trained and certified as a systemic coach and facilitator, and therefore draws upon the work of other skilled practitioners that support companies in finding successful ways to address complexity. Although the article can be easily put in the complexity science and systems thinking area of academic interest, the research questions and insights are intended to serve the learning and the evolution of organizations.