The challenges of today’s world don’t restrict to borders, specific industries or fields of expertise as linear development models may suggest. In order for development to react in a synchronized manner to capture the complexity of these crises, a transition has been initiated within the United Nations Development Programme (UNDP) and the way of doing development, called the portfolio approach. An approach that agrees with the statement Rittel en Webber (1973) that finding the solution to a problem is similar to understanding the nature of the issue. The goal of the new approach, developed by the Strategic Innovation Unit (SIU) of the UNDP is to move from linear project planning to a more systemic and holistic way of working within the discipline. This report follows the online journey of an UNDP team into this new way of doing and discussing development. The journey did not go without hurdles, both external factors, political dynamics and organization hierarchy, and internal factors, adjusting to a new mindset and communication manner, influenced the learning process of the team. Observations of these dynamics has led to an intervention in the domain of communication within the portfolio realm in order to socialize the principles of systemic approaches and bring the team closer to the challenge of concern by discussing its subjective stories. The powers of the universal and context dependent characteristics of physical objects is taken as a starting point. They functioned as a boundary object, a concept that facilitates collaboration between different groups and stakeholders adjusted to different social worlds (Star & Griesemer, 1989) and steers conversation to facilitate connection in the domain of complexity. Experiments with a variety of UNDP members explored the possibilities of the objects. The unusual objects found during this research have proven to spark new information streams and offer specific insights on the subject matter. The project’s accumulated in an elaborate workshop designed to guide CO teams to explore tangible objects in their domain. The objects collected by the team in the workshop serve as valuable tools for the team’s internal collaborations and externalizing perspectives. Utilizing physical objects to achieve this, aims to accelerate engagement, foster recognition and enable context-specific conversations, reinforcing the statements of both the necessity of a portfolio approach and its systemic nature. The project aims to provide fresh perspectives on the transition to a portfolio approach and its communication strategies, contributing to the research on effective implementation and integration of the portfolio approach within UNDP teams. The report presents a practical and an alternative conversation starter on the systemic aspects of the approach in order to facilitate engagement with the approach and emphasize a deeper (personal) involvement of the participants.