Embracing agile values and principles is no longer limited to software development projects, but has become a strategic priority for many organizations. To adjust to a rapidly changing environment and improve overall agility, many organizations with hierarchical cultures, which many believe hinder the acceptance of agile values and practices, need to embrace agile practices and principles, while balancing them with their cultures.  Leadership strategies play an important role in this journey. Interviews with agile leaders in two large organizations revealed three organizational challenges and identified leadership strategies that addressed these challenges during the organizations’ agile journeys.