Do people adjust their conversational strategies to the specificcontextual demands of a given situation? Prior studies haveyielded conflicting results, making it unclear how strategiesvary with demands. We combine insights from qualitative andquantitative approaches in a within-participant experimentaldesign involving two different contexts: spontaneouslyoccurring conversations (SOC) and task-oriented conversations(TOC). We systematically assess backchanneling, other-initiated repair and linguistic alignment. We find that SOCexhibit a higher number of backchannels, a reduced and moregeneric repair format and higher rates of lexical and syntacticalignment. TOC are characterized by a high number of specificrepairs and a lower rate of lexical and syntactic alignment.However, when alignment occurs, more linguistic forms arealigned. The findings show that conversational strategies adaptto contextual demands.