I've been an eyeglass wearer and headset (as well as hearing protection) user for about thirty years. Here's what I've learned:
Everything depends on the thickness of the arms of your glasses. Thus if you have another set of glasses with thinner frames, you might want to wear those with the headset. Otherwise, of course, this point isn't much of a lifehack.
The tighter the headset "squeezes" your ears, the more painful it will be. Do what you can to adjust your headset so that the top of your head bears most of the force, so you can relax the grip on your ears somewhat.
Again, adjust the headset so that the earpiece foam doesn't ride on top of your ears. The earpieces on the headset you linked appear to be large enough for that, but I could be wrong. Still, try repositioning them forward and up somewhat—small amounts until you find the most comfortable spots.
Give your ears a break
This is doubly true if you have the volume turned up, but that's another topic! Take your headset off periodically such as in-between rounds (if you're gaming), and get into the habit of just moving it around slightly every few minutes, before it really starts to annoy you. That will let the circulation back into the parts of your ear that have been put under the most pressure, which will make a big difference. Our ears don't have much bloodflow to begin with, so they can always use a little help in that department.
Another way to give your ears a break is to simply slide one earpiece off of one of your ears, and then switch ears. Obviously you bought a stereo headset for a reason, but if you don't need positional audio or stereo sound at the moment, this can be another handy trick to add.
So what's the "best" strategy?
All of the above. The Stack Exchange way is to have a clear answer, and my clear answer is, the more different ways you can take a little bit of stress off of your ears, the better you'll feel. Like I mentioned, our ears aren't particularly good at pumping blood, which is why moving the pressure points around is the right answer, in my opinion.