The events and disruptions of 2020 and 2021 continue to place demands on CHROs and their teams. This article identifies five top-of-mind issues for middle-market CHROs and offers tips on how best to address them. And while the five issues are relevant to most organizations, the authors submit that these issues are especially difficult for CHROs of midsize firms since “they typically must meet big-company tests with small-company resources.” The five issues include: 1) Managing a return to workforce growth, 2) Reskilling and upskilling employees, 3) Revamping HR systems and processes, 4) Recharging employee engagement and productivity, 5) Addressing urgent diversity, equity, and inclusion issues. About revamping HR systems and processes, I have two questions for leaders to consider: a) Where can we eliminate processes or systems that are extraneous and detract from productivity, innovation, and employee well-being, etc. 2) Of those that can’t be eliminated, which can be simplified while driving a better experience and business outcomes? The authors provide four tips on how resource-constrained middle-market HR leaders can address the five challenges.