The way a business articulates and actions its critical success factors is a major determinant of sustainability and success. Dire times have been predicted for small wineries in Australia, with a high risk of being crushed by the combined weight of competition, changing market structure and evolving consumer preferences. Yet despite these gloomy predications, some small wineries have avoided that crush. This paper presents a case study of how a newly-profitable small boutique winery approaches the articulation and operationalisation of critical success factors in its effort to be sustainable. This winery’s current response has been born of bitter experience, and shows the utility of having a balanced set of critical success factors which promote a reassessment of the fundamental nature of the business from a risk perspective and encourage the re-deploying of resources from the more mechanistic and measurable tasks to relationship building and feedback.