This study explored the experiences of two sets of employed mothers ( n = 32) who returned to paid labor after taking maternity leaves in the United States prior to the COVID-19 pandemic. Interviews with 11 women working in “active” job types (high discretion, complexity, and resources) as well as 21 women working in “passive” job types (low job discretion, complexity, and resources), revealed differences in their negotiation processes and their positive communication with their managers. Women in active positions co-constructed feminist negotiations with hybrid strategies attending to organizational and their own health priorities and enabled by positive communication. In contrast, women in passive positions did not perceive workplace policies or interactions with their bosses to be flexible, negotiable, or resembling positive communication. Implications consider further research on structural opportunities and constraints to negotiate work-family policies and practices such as ongoing conversations and/or workshops on the benefits of and training in positive communication for employees’ health and well-being.