Objective: The primary purpose of this study was to use an ecological assessment model to obtain a better understanding of difficult situations that home visitors confront when implementing home visitation services. Method: A mixed method study was used which included conducting focus groups to identify specific situations faced by home visitors who implement the Healthy Families America model of child abuse and neglect prevention. The results of the focus groups were used to design a survey. The survey had 91 Healthy Families home visitors rate situations according to frequency and difficulty. Results: The results revealed that situations that were ranked most difficult included working with families where there are limited resources, where family mental illness is present (e.g., threatening suicide), where there is substance use in the home, and where families are unmotivated. A factor analysis of the situations produced five factors that reflect the difficulty of doing home visitation: having a lack of clinical skill, addressing family difficulties, addressing parenting difficulties, resolving personal difficulties, and having a lack of experience. Conclusion: The situations identified in this study can assist in developing the competencies needed by home visitors. The factor analysis results can be conceptualized into an inventory for staff supervision, with workers completing the inventory to identify individual areas of training needs.