The purpose of a mechanism in organic chemistry is to show the movement of electron density leading to the reaction. Keeping this in mind, when faced with the starting materials, the first thing to identify is to find the most electrophilic and nucleophilic groups in each molecule. The electron density will always move from the strongest nucleophile to the strongest electrophile.
First take a look at the molecule. Are there any negative charges? If so that’s the starting point in most cases, if not, have a look for lone pairs and lastly - double bonds. These are nucleophilic species and good initial starting points; the more electron density is in one point the better the nucleophile. With electrophiles it’s opposite – best electrophile will have the lowest amount of electron density at one point e.g. a carbon adjacent to an electron withdrawing group or near a positive charge. However, be aware that you can’t for 5-valent carbons, so if you form a bond to a carbon then you must break one as well.