Since you are using the 550EX, you have the luxury of using high speed flash sync at any shutter speed. Higher speeds decrease the effective range of the flash, but this is rarely a problem in fill situations.
If the face is turned away from the light with the sun providing highlights on the hair and shoulders, and the background is not overly light in tone, I usually set the exposure manually to about 2/3 to one stop over a sunny-16. Set the exposure compensation on the flash to about -1 to 1 2/3 (I turn off the automatic flash reduction with the approriate CF), and shoot away.
If you prefer you could meter the background manually and open up a stop or so, if it is a light toned background (sunlit sandy beach for example), close down a stop or so if it is dark (shaded trees for example). This will generally provide a subject background balance that appears natural to the eye. But this is of course not a hard and fast rule, feel free to vary the compensation on the background to your taste. You definately want to set the flash compensation to atleast 1 under, since the operative concept here is to fill but not to over light the face.
This is the type of thing where you just have to experiment a bit. Any advice should be taken only as a starting point. Differences in metering methods, personal taste, etc. will cause your mileage to vary.
You're fortunate in that you can immediately preview the results with your IDs.