Agricultural advisors have recently received much critique both in practice and in the literature for not answering agricultural entrepreneurs’ need for support in the ongoing industry transformation. Advisors expect to guide highly pressured agricultural entrepreneurs operating in complex settings towards sustainable businesses in highly competitive markets. This chapter, using complexity leadership theory, goes beyond the surface of the agricultural advisors’ everyday work by exploring challenges faced by the advisors and considering how to overcome them. The advisors’ genuine intentions and common mission guiding the development of sustainable agricultural businesses and a vibrant countryside is not enough to achieve the goals. The authors identify an emergent need for innovation in the leadership of advisory work and conceptualize enabling mechanisms to accomplish such change. They suggest that the creation of adaptive space as a lubricant gives innovation the opportunity to flourish through enabling leadership.