This Solah is offered when a Muslim encountered a difficulties in decision making as Allah SWT is the Most Knowing of all the unseen and will InsyaAllah guide us in which the matter will be good regarding our religion, our livelihood and future well being.
Ahadith concerning Istikharah solah.
Jabir Ibni Abdullah RA narrates that Rasulullah SAW used to teach us the way of doing Istikharah with as much importance as he used to teach us the Surahs of the Qur'an.
Rasulullah SAW said: If anyone of you intends to do any work (and is concerned about its final outcome) he should offer two Rak'at optional Salat and supplicate:
Note: Istikharah means asking Allah for suitable guidance. For instance, it is desireable to perform Istikharah if a person intends sending a proposal somewhere.