Younger brother to the Master, Maheboob was extremely musical, intelligent, and thoughtful, but also very retiring. Their grandfather Maula Bakhsh recognized in him a great gift of improvisation, and trained him together with Inayat in music. As he grew up, Maheboob was exposed more to European music than Inayat had been, and he conducted some orchestras, and took some interest in Western musical theory. When Inayat began to travel from Baroda, he entrusted his musical students to Maheboob, and felt they were well cared for.

When Inayat sailed to the West in 1910, Maheboob left a promising musical career and accompanied him, supporting the Master in his travels and throughout the many difficulties that he faced. In time Maheboob settled in The Hague, marrying a Dutch mureed, Shadbiy van Goens, who bore him two children, Raheemunnisa and Mahmood.

Hazrat Inayat Khan felt that his brother Maheboob had a particularly beautiful voice, but Maheboob was so shy that he would rarely sing for others. There is a story that Inayat and his brother Ali Khan would sometimes pretend to go out, slamming the front door and then waiting quietly in the front hall in order to hear Maheboob practise his singing.

Maheboob also composed many beautiful sacred songs.It is further testimony to his great diffidence that when Maheboob at last composed a song on a sacred poem by Inayat ('Before You judge.') he could not bring himself to show it to his brother, and the Master passed away without having heard it.

Upon the passing of the Master in 1927, Maheboob took the heavy responsibility of leading the then very young Sufi Movement, becoming the Representative-General, a post he held until his own passing in 1948. These years were not happy ones for the members of the Sufi Movement, both for the loss of Hazrat Inayat, and for the clouds of discord and war that enveloped the world. Nevertheless, Shaikh-ul-Mashaik Maheboob kept the flame of the Message alight through a very dark time, and he is remembered with love, respect and gratitude.