Over the past 30 years, the world of IT and software has evolved from on-prem infrastructure and siloed teams to cloud-native platforms, AI-driven workflows, and globally distributed engineering organizations. Through that journey, some lessons have stood the test of time, while others have been learned the hard way. In this session, I’ll share the most impactful lessons from my career, covering what truly drives successful technology initiatives (and maybe some life lessons), where organizations commonly go wrong, and how leaders can better align people, processes, and tools to deliver real business outcomes. Attendees will walk away with practical insights they can apply immediately. And there may be a few that are more life lessons to help future decision making. Whether they’re modernizing legacy systems, scaling engineering teams, or navigating the rapidly changing landscape of AI and digital transformation, this short Ignite talk will provide a lot in only 5 minutes.