Answered by Sayyidi Habib Umar bin Hafiz (may Allah protect him and benefit us by him)
What are the signs that indicate that a spiritual traveller is progressing?
The signs are: that he has a desire to attain that which Allah possesses; that he has an increase in love for Allah and His Messenger ﷺ; that he finds comfort in acts of obedience; that he is repulsed by acts of disobedience; that he finds comfort in the remembrance of Allah and that he has an increase in longing to be in the company of the Messenger of Allah ﷺ.
He can also assess his progress by assessing his hope, fear and veneration of Allah which helps him to increase in love. Whatever state the seeker is in, he is likely to make mistakes but the sign of his progress is the speed at which he repents and returns to Allah.
What are the signs that indicate that a spiritual traveller is remaining stationary and not progressing?
There is one sign: that he is not seeking an increase in a good way.
What are the signs that indicate that a spiritual traveller is sliding back along the path?
The signs are: that he inclines towards acts of disobedience and transgressions and feels an affinity towards those that commit them.