“Designers are about possibilities. Engineers are about probabilities.” This quote, from Stephen Deasy, Head of Cloud Engineering at Atlassian, is just one example of how concisely he can describe the relationship between designers and engineers. Our interview with him was our first chance to learn from a leader on the engineering side, and he shared a wealth of knowledge that will help designers work more effectively with their engineering counterparts. Stephen gave us insights about running regular retrospectives and health monitors with your team, and “plays” like Roles and Responsibilities. He also spoke to the mindset and process shift that occurs when teams scale from 15, to 50, to 150 people. Stephen also relayed some great insights on design and agile.