In today’s complex world, most businesses and companies experience different confusing strategy issues. Most of these problems are not just persistent or severe but are labelled as “wicked” in some areas of practice such as urban planners. In this context, the term ‘wicked problems’ refers to those issues which companies and businesses cannot resolve definitively. This paper proposes that applying wicked solutions to wicked problems might be an effective strategy that requires an appropriate decision-making approach by senior leaders of business organisations. It also provides ways of measuring outcomes of some strategic decisions. The paper will use the existing body of knowledge and different conceptual models to investigate the research idea empirically in a sample of senior leaders and CEOs.