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Higher education institutions have increasingly needed to balance college affordability with institutional financial sustainability. This qualitative study leverages General Systems Theory (GST) to examine phases of adoption of income share agreements (ISAs) at four U.S. institutions of higher education. Eight institutional leaders from four schools were interviewed about the decision-making process their institution underwent when implementing ISAs. Environmental inputs include the need for discretionary funding, an adaptive leadership culture, and a defined crisis. Behavioral throughputs include low to high levels of direct leadership engagement. Outcomes were impacted by the closure of ISA programs, but the GST model includes confirmatory returns on investment and smaller-than-anticipated student cohorts. Further exploration of the GST framework could unlock additional insights on college affordability.