Answered by Sayyidi Habib Umar bin Hafiz (may Allah protect him and benefit us by him)
Will the Student be with his Shaykh in Paradise?
The members of a family who lived in faith and obedience to Allah in this life will be reunited in Paradise. Allah says: “those who believe and are followed in faith by their descendants – We cause their descendants to join them.” 
Likewise, if the shaykh and the student both honour the covenant which is between them, they will be united in Paradise. According to the truthfulness of their love and their attachment, the one who is in a lower station will be raised to the station of the one who is higher.
Brotherhood for Allah’s sake is greater than blood brotherhood. The relationship between the shaykh and the student is like the relationship between father and child, but it is greater since through that relationship the student receives knowledge and light. The first relationship is spiritual, whereas the second is merely physical.
 Al-Tur, 52:21