Answered by Sayyidi Habib Umar bin Hafiz (may Allah protect him and benefit us by him)
Should the seeker inform his Shaykh about all of his affairs?
He should refer to his Shaykh concerning those affairs which require clarification and guidance, or that which the Shaykh has asked about, or those things which are related to the affairs of spiritual wayfaring of his heart, or actions of the limbs.
The awe-inspiring nature of the Shaykh should not prevent the seeker from asking. He should not think it is good etiquette not to ask the Shaykh about such matters.
If he is unable to consult the shaykh on a certain issue, he may rely upon the principles that the shaykh has laid down previously to come to a decision.