Answered by Sayyidi Habib Umar bin Hafiz (may Allah protect him and benefit us by him)
How does the seeker know if the Shaykh is pleased with him or her?
The sign of this is true love in your heart for him and also your being content with that to which the Shaykh guides, invites and leads. This is reflected in your being well-pleased with Allah as your Lord and our Master Muhammad ﷺ as your messenger and Islam as your religion, and your true desire to follow and to emulate the Messenger. These are all signs of their good pleasure.
May Allah grant us His good pleasure, the pleasure of the shuyukh, of our parents, of the elders, of the pious – none of these are sought except as a means to Allah’s good pleasure and the pleasure of His Messenger. It is more fitting that they please Allah and His Messenger if they are truly believers.1
1 Al-Tawbah, 9:62