This article explores how estates in the Scottish Highlands were managed after the clearances. The land system had been radically redrawn, creating consequences that those who inherited the post-clearance world endeavoured to manage. At the centre of the post-clearance Highlands were the estate managers, or factors, who were effectively responsible for the economic and social conditions on their employers’ estates. They controlled the levers of Highland life and faced the realities of the post-clearance order. Prominent among this group was Evander McIver. This article examines McIver's career up to 1873, framed by a discussion of the ‘Highland Question’ of how estates reacted to the continuing poverty and occasional destitution of their small tenants, or crofters. McIver held adamant views on this question, and the origins and expression of these views through his career are delineated in this article.