The researcher seeks to address the needed changes to superintendent evaluation by suggesting an integrated formative evaluation process that balances both the need for accountability and ongoing professional growth and support (Hallinger, Heck, & Murphy, 2014; Duke, 1990). The nuances of the superintendent and school board relationship present unique challenges that create additional obstacles and opportunities for establishing and maintaining a cyclical formative process for evaluation. A brief overview of research that includes a rationale and overview of current challenges to the superintendent evaluation process are also discussed. Practical tips for improving the evaluation process including adoption of a standards-based framework, utilizing stakeholder input, providing board director professional learning and ongoing support are offered.