Engineers Haris Rozajac and Nathan Marrs at Grafana Labs explored transitioning from individual contributors (ICs) to engineering managers (EMs) to expand their leadership skills and tackle organizational challenges at a hyper-growth startup. They discovered that Grafana Labs supports a dual-track career progression, allowing engineers to switch between IC and EM roles without losing their current standing. Through interviews with colleagues who have successfully made this transition, they learned the importance of self-advocacy, organizational environment, and luck in facilitating a move to management. Key attributes for a successful EM include empathy, effective communication, technical proficiency combined with delegation, and a focus on mentorship. The authors emphasize the importance of being prepared for opportunities, advocating for oneself, and seeking experiences that enhance leadership capabilities. Grafana Labs' supportive environment and insights gained from peers have bolstered their confidence as they pursue this career path.