As higher education institutions embark on enterprise system modernization initiatives, the successful conversion of legacy data to the cloud is critical to the project's overall success. Grants data is both financial and biographical, and transactional data can span decades. These factors make the conversion of Grant's data one of the more complex conversions that an institution will face. Data conversion impacts the success of the overall initiative, and it is a crucial determinant of the overall user experience and adoption of a new system. The significance of conversion is amplified as higher education institutions have unique reporting and compliance requirements, unlike most commercial organizations. This presentation focuses on leading practices, lessons learned, and provides institution leaders insight into finding the right balance for how much and what data to convert from the legacy system to the cloud.