Although the literature regarding associations between young children's social emotional competencies and their executive functions (EF) is growing, there continue to be divergent accounts of the relationship between specific challenging behaviors (e.g., impulsivity, aggression, defiance, short attention span, withdrawal) and particular EF deficits (e.g., poor attentional control, flexibility, inhibitory self-control, working memory, and/or planning/organization) in young children. This mixed-methods study explores this relationship for a population of 19 preschool children. The study includes analysis of interviews with parents, teachers, and early childhood coaches for 4 of the children. Results demonstrated a significant relationship between teacher reports of challenging behaviors and deficits in global EF skills. In addition, participants provided a rich qualitative description of the children's challenges with inhibitory self-control, flexibility, and attention control. Oppositional or defiant behaviors were also prevalent within this group of 4 children. The constellation of difficulties for these children has implications for adults aiming to support positive social development and suggests next steps for research regarding behavioral targets and strategies and the collaborative parent-professional team efforts needed to address the children's needs.