daily life: can't get it out

I'm not an expert screwer, I probably only screw a few times a year, Christmas generally involves some screwing. Screwing is hard enough, but it's made all the worse when the previous screwer has left behind a shattered mess.
How difficult is it to look after the head while screwing? It is after all the most important part of any screw, you need to care for the head, touch it gently, definitely don't apply too much pressure, and if you go too fast the head just explodes in your face and the whole thing will be an exercise in futility.

Remember, when you screw be gentle with the head.