Evaluating programs in remote Indigenous communities requires contextual consideration and a degree of connection that goes beyond the usual focus on output measurement and system monitoring. Evaluators who are experienced with working in remote communities become more and more cognisant of the issues and complexities that impact the quality of evaluations. As this reality presents itself, evaluators rely more and more on the help of the local community to explain and reveal such realities. A learning journey takes place that allows ‘outsiders’ to be accepted into the community and be part of a productive matrix of support and ‘insiders’ begin to assume their legitimate rights to participate, advise, educate and guide evaluators. Without a participative and collaborative styled process, evaluation risks being non-reality based without a guarantee of quality and has the potential to impact the community in a negative way. This paper presents the views and experiences of ‘insiders’ and ‘outsiders’ who have been involved in evaluations in remote communities. Their collective views demonstrate the need for a two-way approach that establishes middle ground for a respectful and quality evaluation process. This approach ensures evaluation remains relevant and purposeful for those who are impacted by the program outcomes, providing a focus on the everyday reality that depends on cultural responsiveness and ensures legitimacy for Indigenous people.