Dissatisfaction with inflexible top‐down development interventions has led to a demand for more community‐led approaches and the proliferation of terms such as participation, empowerment, and community ownership. However, the practical implications of these terms remain unclear. This study examined how sociocultural factors influenced relationship building between NGO staff and community members, and how this mediated community participation in a child education and women's rights intervention in Kolkata. Twenty interviews and one focus group were conducted with NGO staff, pupils, and members of a women's group. A thematic analysis produced five global themes: Sociocultural Context, Staff–Community Divide, Power Dynamics, Building Relationships, and Unstable Progress. Differences in social status, lifestyle, and priorities marked clear divisions between staff and community members, leading to communication difficulties and resistance ranging from suspicious stares to open hostility. Establishing mutual respect was a slow and unpredictable process often fuelled by unanticipated events such as staff helping with medical emergencies. A campaign against domestic violence prompted some women to physically attack men and vandalise property, provoking violent retaliation and creating divides within the community. Overcoming these challenges required a responsive approach which often deviated from operational and funding plans. The more participatory and community‐led an intervention, the less predictable it becomes. The flexibility needed to gain community acceptance and manage unanticipated events relies on trusting relationships between both communities and staff, and staff and donors. Copyright © 2012 John Wiley & Sons, Ltd.