When it comes to aligning technical and business strategies, it’s important to approach the process with a holistic and collaborative mindset and include a diverse set of key members of an org. Rather than viewing these strategies as separate entities, it is crucial to understand that they should be jointly developed and complement each other in order to drive the overall success of the implementation. Yes, these planning meetings can be stressful, confusing, and long, but you’ll be much better off abiding by the measure twice, cut once philosophy.