Robert Leonard began his curatorial career at the National Art Gallery (now Te Papa Tongarewa) in Wellington.

[4] Leonard left New Zealand in 2005 to become Director of the Institute of Modern Art (IMA)[5] in Brisbane, Australia, where he remained for the next eight years.

Commissioned by the MCA in Sydney,[11] Headlands sparked discussions around Internationalism around who or what should represent New Zealand art and cultural appropriation focusing on the koru series of paintings the artist Gordon Walters started with the work Te Whiti.

[14] Leonard also curated Gavin Hipkins: The Colony for the 2002 São Paulo Biennial[15] and the New Zealand presence at the Asia Pacific Triennial in 1999.

Its first publication was The Homely II,[44] a photographic project by Gavin Hipkins co-published with City Gallery Wellington.