Answered by Shaykh Faraz Rabbani
Walaikum assalam,
The istikhara prayer is very simple: one prays two rakatsat any time that is not disliked, after which one recites the supplication of istikhara.
It is best to recite it before sleeping, though in no way necessary. One should suspend one’s own judgementor inclination about the particular matter, and wait for Allah to show one a sign or to make things happen in a way that indicates what to do. If unclear, it is recommended to repeat the istikhara prayer and supplication seven times. Shaykh Nuh Keller mentions that the more one prays the istikhara prayer, the clearer its answers become to one. He prays it for all matters, even things one would not imagine doing istikhara for.
If stuck in a situation where it is not possible to pray, one may limit oneself to the supplication alone. This is what women in menstruation should do, too.
The great living Hanafi scholar and hadith expert from Aleppo, Shaykh Abdullah Sirajal-Din mentions in his book on the virtues of prayer that it is the way of many Sufis, including Shaykh al-Akbar Muhiyyuddin Ibn al-Arabi(Allah sanctify his secret), to pray the istikhara prayer at the beginning of their day, after sunrise, asking Allah to guide them in general to all good and to keep away all evil from them.
We ask Allah to give us beneficial knowledge, and the success to act upon it in the way most beloved to Him, on the footsteps of His beloved Prophet Muhammad (Allah bless him and give him peace).
Wassalam,
Faraz Rabbani.
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