Enterprises are not new to technology outsourcing, but many disclose that it is difficult to achieve the intended benefits. Some find that these relationships tend to chafe for years under unending frustration. Fortunately, there is a better way. Modern practices seek common value with partners, leverage a mix of pricing models, embrace flexibility and continuous improvement, and incorporate modern technology and improvements like automation, observability, site reliability engineering (SRE), and value stream management (VSM). This assessment helps organizations evaluate their competencies in each category and direct them toward a more mature technology outsourcing practice.