Digital transformations are often viewed as a competitive sprint rather than an enterprise journey. Nearly all services decision-makers in Forrester’s Business And Technology Services Survey, 2022, have or anticipate challenges in executing digital transformation. However, there is no alternative to transforming traditional organizations into more adaptive, creative, and resilient ones. This report lists the most common challenges in digital transformation execution and provides essential research, tools, and templates to help technology executives address these obstacles while implementing their transformation roadmap.