Your method will be specific to your equipment.
My pot will boil 3.25gal (total 4gal) but for comfort's sake I keep it at 3gal throughout the boil.
My method is to boil 2gal and dump into my fermenter and let that sit in a cold water bath throughout the boil to bring it to room temps.
Then I figure out how many =<3lb DME additions I will be making. Let's say 8lbs of DE?M are going into this batch. This makes a total of 3X =>3lb DME additions (3lb, 3lb, 2lb). I stagger my DME additions to facilitate hop utilization and lessen the final color. So, for this example I am going to add 3 DME additions and I boil each addition individually in a separate pot using 1 quart of water so that it is fully dissolved and does not disrupt the boil when added to the boil kettle.
I also know through experience that my boil kettle will lose almost exactly 3 quarts of water over the course of a 60 minute boil.
So, if my target boil volume is 3gal and I am adding a total of 3qts with my DME additions but I will lose 3qts to evaporation then I will make my initial boil volume 3 gallons.
In this way, once the boil is complete there are 3 gallons in the kettle and 2 cooled gallons in the fermenter. I can get my kettle down to 80F in 15 minutes using a circulating ice water bath in the sink. Dumping the kettle into the fermenter gets the whole 5 gallons down to room temps and aerates the wort (although I whip it with a whisk, too).
I keep an eye on my boil kettle because I know where the 3gal line is (you can scratch it in if you need to) and adjust additions as needed to keep a 3 gal volume. At any rate I always nail exactly 5 gallons into the fermenter unless I'm specifically shooting for a different volume.
As you can see, your equipment and your method will dictate exactly how you go about hitting target fermenter volume.