Because of their overreliance on benchmark tracking, pension funds in Switzerland tend to take a passive and short-term approach to portfolio investment and management. This leads to mismatched and sterile strategy styles in relation to their mandate’s perspective and needs. Pension funds have a long-term perspective which nevertheless could benefit from more adaptive approaches (for example, in seeking to temper the negative effects of the paradigm shift to near-zero interest rates which has plagued performance for several years now). In this study, we aim to explore and understand alternative approaches used by successful market participants. The inductive methodology used is a qualitative survey based on the collection of narratives through semi-structured interviews. We conducted 9 semi-structured interviews with experts in the field to explore this question and develop research proposals. Then a synthesis is made based on a categorization by theme. Thanks to this synthesis, research hypotheses are generated and compared with the scientific literature. The key findings are that talented finance professionals look for weak signals that herald change and they can exploit them successfully. We aim to see if there are benefits to incorporating qualitative weak signals into a forward-looking risk management tool to better hedge the portfolios of pension funds that typically rely on more backward-looking approaches. The objective of this research is, therefore, to apply the concepts of cybernetics to the case of a business investment portfolio solution. These results will be introduced in further research in our quantitative and digitized forward-looking portfolio management models.