In many schools and businesses today, the pressure to produce results is far greater than attention to employee learning. If continued learning impacts service for business customers and their communities, then what lessons can be learned from business to support and advocate for educator learning? This article is a collection of lessons learned by an educator and human resources professional over the course of separate careers in education and business. The authors share their individual perspectives and reflect on their experiences as a whole. The hope is that the lessons learned will be helpful to those developing and supporting employee learning in business and education. Their conversation raised important questions about what kinds of learning resources are the most relevant and useful in both environments. They aimed to identify lessons learned from business and education that could help improve outcomes, specifically to serve customers and communities in business and how educators acquire the knowledge and skills to support student achievement in schools. They found some common practices that could be used to a greater extent to sustain professional development in the school and workplace.