Background: Parenting strategies such as communicating clear expectations, providing calm directions, and teaching specific skills can strengthen young children's social-emotional development. Parenting programs for children with disruptive behavior often emphasize gaining compliance via effective directives, and less on how to facilitate child skill acquisition or on effective parenting for differing situations and task demands. Objective: We aimed to study how parenting strategies and associated child behavior vary by situational contexts. Specifically, we focused on the differential use of directives and guidance during different tasks. Method: This observation study utilized a microsocial coding system, the Parent-Child Play Task Observation System (PCPTOS), to closely examine parent and child interactions in multiple analogue task situations. The study drew on pre-intervention data for 224 parent-child dyads who participated in a parenting-focused intervention trial for children ages 3-7 who presented elevated levels of disruptive behaviors. Results: Interrater reliabilities were very good to excellent. Parents used directives more frequently during the clean-up task and guidance more frequently during the teaching task compared to the other tasks. Associations of parent use of directives and guidance with child behavior and affect differed by task. Observed parent directives were associated with child disruptive behavior during each task, whereas parent guidance was negatively associated with child disruptive behavior and positively associated with child positive affect during the teaching task. Conclusions: Parenting strategies that are well matched to the situational context and proactively consider task demands are more likely to facilitate children's social-emotional development.