All leaders—from new managers to seasoned executives—must delegate tasks to free up time and attention for the big-picture work their more-senior roles demand. But too often leaders find themselves caught in the weeds of execution. This article helps leaders determine which work to keep and which is better left to a team member. Then it identifies four challenges that stop even those who know how to delegate from doing it successfully: (1) an addiction to the dopamine hit of easy productivity, (2) a disinclination to reject requests for help, (3) a desire to meet their own bosses’ or clients’ unmanaged expectations, and (4) a misunderstanding of what “work” should mean for a manager. Drawing on research and two decades of experience advising senior leaders, the author offers concrete recommendations for overcoming each challenge. Even for leaders with the best of intentions, overcoming these challenges will take time. However, if you stick with it and learn to delegate effectively, you’ll get much more out of your team members—and yourself, as a developer of talent and as a big-picture, strategic thinker.