This article describes the role of the skillful leader and what practical solutions are needed to overcome hurdles. What distinguishes the skillful team leader from a less-effective leader is his or her approach to overcoming hurdles, and are rooted in the leader's values, mindset, intelligence, and skill. When faced with hurdles to team learning, the skillful team leader relies on their strong commitment to five foundational values: collaboration, shared leadership, goal setting and attainment, rigorous discourse, and continuous improvement. The skillful team leader will view hurdles as obstacles to overcome but also as windows into the complex world of school culture. The skillful team leader knows that addressing a problem specific to their team without a deep look at how school culture contributes will only give rise to the hurdle again. The skillful team leader not only works with their team to navigate around the hurdles that school culture gaps cause, but also works to close those gaps so all teams can succeed. Reflections from each hurdle encountered aids the skillful leader to better understand the complexity of leading, how to anticipate and avoid hurdles; and how to effectively respond.