The article examines the role of Sufism, its awliya’, and transnational tariqas (Islamic mystical brotherhoods) in the history of Islam and Islamic thought. It does so by focusing on the Naqshbandiyya tariqa, which is the most widely disseminated across various regions of the world, including Sumatra, Indonesia, Turkey, and Uzbekistan. The Naqshbandiyya tariqa, which originated in Central Asia during the 8th / 14th century, is amongst the oldest brotherhoods. Moreover, the article sheds light on a lesser known aspect of Sufi leadership tradition, specifically the role of the shaykh as a mediating agent in the Naqshbandiyya of Sumatra. The Islamic society can be viewed as charismatic due to its embodiment of the authority of Muhammad. Accordingly, this study presents the important aspects of the traditions linked to the ideal of the Prophet as practised by the local spiritual leaders. Additionally, today they act as mediating shaykh s, which empowers Muslims to pursue a spiritual path amidst conflicting situations and pressures of modern life.