There is a challenging truth many IT teams and developers have experienced; that although learning is a core DevOps principle, products and training designed to help engineering teams rarely produce the outcomes to justify the time and money spent. Using our recent experience working with Grafana, GitLab and Navy Federal Credit Union to develop a new training approach, we’ll explain what we’ve learned about the failed modalities of how engineers have been learning new technology skills, and the processes they need in order to be productive. We’ll also highlight exactly why this ineffective type of learning style has come to permeate the marketplace. We’ll tell the story of the friction, obstacles, and constraints we encountered during this exploration, and what we heard IT teams ask for instead so they could not only succeed in learning new technology, but also in implementing faster, more secure and more efficient DevOps pipelines with confidence.