Francis Newbery, Director of the Glasgow School of Art 1885 and1918, produced a painting which depicted the deliberations of the School’s governors as they commissioned the building of new school premises designed by Charles Rennie Mackintosh. The painting was acquired by the School in 1914 and hung in the Board Room. A mixture of deliberate technique and fortuitous circumstance in the creation of this work seems to have made for a canvas saturated with meaning in the evidently discordant complexity of its representations of time and space. An examination of the painting is used critically to engage with the story of the creation of Mackintosh’s masterwork, and to contextualise the process in which the latter was produced as a significant work of art.