The issuance of parliamentary questions (PQ) in presidential democracies reflects an effort to connect with the electoral constituency to advance the legislator's career. We postulate six hypotheses on the association between party affiliation, career advancement and district-level incentives and the issuance of PQs in Chile's presidential multiparty democracy. We test them using a novel dataset containing 68,424 inquiries (oficios legislativos) issued by Chamber of Deputies legislators in three legislative terms (2006–2018). Though district-level variables play a role in the issuance of PQs, incentives of political ambition do not. As opposition coalition legislators make more use of PQs than ruling coalition legislators, there is preliminary evidence to associate PQs with a possible oversight role.