I would NOT use a 3/8 drill. (one time deal? Pick up a HF 1/2" angle drill)
I have drawers full of all types of drill bits. I'm constantly drilling through thick timbers, barn beams, treated, & RR ties.
RR Ties & 6 x 6" treated lumber,,, I'm Drilling slightly undersize holes for re-bar pins or long lag bolts.
Seems like, I always start out with the brad point or auger bits. & Lubricate the sides with a shot of used oil.
OR I just use an extra long H F TWIST steel bit,,,, & sometimes, I'll change the angle on the cutting edge. Ya, You'll have to 'In & Ou' more often, to throw chips, but THEY DO NOT BEND when jammed up or when hitting something hard.
I'd love to see a picture of your project. ?
If your stacking ties or treated timbers for a retaining wall,,, I would place some 'DEAD MAN' concrete mesh on top of each layer of ties, back into the dirt fill.
AND, if your subjected to WINTER frosts, place about 1' of 57 stone behind the ties, then filter fabric, then your earthen fill.
I'd hate to see walls PUSH OVER & out.