How dull is the chain? Is it producing sawdust or nice long clearly defined cuttings?
In short you’ll need the correct file for your chain. The chain is supplied with the information and size of file required to sharpen the teeth. The file can be bought with a guide to help keep it at the correct angle. After you’ve sharpened the chain a number of times the cutting teeth begin to reduce in height and the depth gauges need filing down accordingly. There’s loads of vids on Youtube covering this.
Regarding frequency, I have a quick look at my chain every couple of hours whilst cutting clean wood up off of the ground. If the chain ever gets buried in the dirt, hits a nail or old piece of embedded debris it’ll probably need sharpening straight away.
Once you know what you’re looking for, the easiest indicator of chain health is the consistency of the cuttings. Dust = blunt…Long ribbons of freshly cut wood = sharp. Again, plenty of info on youtube.
D.