The enterprise resource planning (ERP) industry is a billion-dollar software industry with two prominent higher education ERP companies bringing in a combined $14.27 billion the third quarter of their 2024 fiscal years (Oracle, 2023; Workday, 2023). ERP systems stemmed from materials resource planning (MRP) systems in the manufacturing industry (Jacobs & Weston, 2006; Lowson, 2002; Nowak, 2021) and were designed to mitigate risk, centralize data, and create consistency (Albarghouthi et al., 2020; Alhazmi et al., 2022; Kumar et al., 2022; Liu et al., 2023; Rubel et al., 2023). Multiple sources indicate that the failure rate of ERP systems within higher education institutions (HEIs) surpasses that of other sectors, which is why it is essential to examine critical success factors of ERP implementations (Albarghouthi et al., 2020; Alhazmi et al., 2022; Kajbaje & Kamatchi, 2022; Skoumpopolou et al., 2022; Soliman & Noorliza, 2020). This study aimed to explore the practical strategies for ERP success by analyzing lived experiences of leaders at two-year community and technical colleges in the upper Midwest. The exploration was achieved by conducting a qualitative phenomenological study that consisted of semi-structured interviews with 12 leaders at three sites. There were eight interview questions; two were introductory demographic questions. There were six detailed interview questions, with two specifically addressing the research question, and four designed to lead participants into a more in-depth analysis of factors related to leadership approaches and ERP project success factors. Interviews were conducted via Zoom and in-person, based on the participants’ preferences. The interview transcriptions were analyzed via Atlas.ti using a thematic coding approach resulting in four themes: (1) project and change management, (2) strategic guidance, (3) resource alignment and allocation, (4) vendor and software. Theme one is comprised of eight sub-themes covering specifics about change management processes and systems to support informed decision making, governance, and standardization, accountability, communication, stakeholder involvement, a third-party project manager/consultant, business process re-engineering, focusing on the student experience, and training. Theme two outlines that executive involvement and support is needed to prioritize the project, coach and empower employees, remove barriers and break down silos, and acknowledge challenges. Theme three is focused on ensuring a strategic project team with the necessary skills and experience are involved in the project, and that workload is managed for these resources. Theme four is centered around the vendor and software, which demonstrates that leaders need to ensure their organizations select software that is mature, integrates well with other systems, and is from a collaborative and supportive vendor. There are six practical recommendations derived from the study findings to guide leaders in future ERP implementations, which are centered around specific actions for executive involvement, accountability, governance, a third-party project manager, communication, and ERP selection. Recommendations for future research include a larger sample size to address generalizability, conducting a similar study using grounded theory to delve further into the meaning of the data, and to study failure rates based on shared definition of failure.