Purpose. Firm level case using action research (AR) to investigate constraints to productivity improvements leading to sustainability (social, economic, environmental) to help organizations and municipalities understand how firm behaviour slows adoption of action on social agendas, such as sustainability. Methodology. Action research involved attending to a single organization for 12 months to observe two organization selected projects using multiple qualitative methods, observation, an interpretive reflection through cycles of action and evaluation. Methods where used as interventions to inform the action team and design further project interventions. Findings. Research findings included limits to organizational capabilities regarding strategy and standards, objectives and measures, structure, and skills development, which were constrained by learning and inertia, knowledge, and founder created culture. This limited the organizational members to reacting to external market forces, internal dilemmas, or nonpecuniary whims of management. Originality. This exploratory paper offers a specific case of organizational constraints led by a foreign founder in the senior living industry by using action research as an intervention. Originality is marked by the observation of constraints without directly inquiring into those constraints, as opposed to most other studies reviewed. I make specific recommendations for the business and municipal government to work towards reciprocal benefits. The paper also gives insight into the challenges of a doctoral study using action research, and the design and conduct of that research methodology as an organizational outsider.