I'm having trouble following your question.
28 drill = .1405
#8 = .164
So a #8 screw wont fit through a .1405 hole.
You must be completely eliminating the hole with the size of your CSK, which makes sense as you call it a pilot, so changing pilot drill dia wont make a difference.
I think the above 2 posts should cover you though.
Machineries gives suggested 'clearance' holes, for #8 I believe this is .194 (10 drill) for a 'normal' clearance.
Size of CSK is driven by head sharp diameter assuming you want the resultant fit to be at or below flush.
Max sharp head dia for #8 hex flat head is I think .359 (phillips etc are slightly smaller). So you can do the math at 82° or 100° and work out at which point you need to CSK the mating part or use undercut screws.
KENAT, probably the least qualified checker you'll ever meet...