Answered by Sayyidi Habib Umar bin Hafiz (may Allah protect him and benefit us by him).
The signs that your connection is sound are:
a keenness to follow his teachings and emulate him;
a feeling of ease and contentment when you hear his qualities and instructions being mentioned
witnessing that he is the door to closeness to the Best of Creation ﷺ and to attaining the pleasure of Allah.