Funds raised from philanthropic giving have become a key element in the long-term finances of higher education institutions around the world, presenting leaders, primarily principals, with a range of novel challenges that have not, hitherto, been key drivers of leadership. This article explores the problem by reporting on qualitative research that looked at how fundraising is carried out in the Malaysian higher education system, which has recently experienced profound changes to its financial landscape. Data were generated by semi-structured interviews with fundraisers from a range of higher education settings. It was found that for fundraising efforts to succeed, they must be spearheaded by an active principal who adopts the stance of transformational leader towards potential donors, forming a long-term relationship based on a shared vision. He or she is likely to be supported by a fundraising team that will be more transactional in approach and style.