I just knew
@pontiac428 was going to say what he did.
There are various styles of sharpening drills, and drill jig aid sharpening machines that require any sort of rotation movement with tilt use the smooth face style (conical sharpening). There is also the "two-facet" style where each flute gets a straight flat cutting edge, and then a separate facet further back, to cut back the rest of the drill bit at an angle, so that that part does not rub over the steel the front edge just cut.
,
The face should be smooth, with no bumps. There needs to be the little straight bit that goes across the point, between the cutting edges. The angle is supposed to be 59°, but can be 60° at a pinch. Stick a couple of hex nuts together with superglue if you need a quick 'n dirty gauge.
I have been sharpening these drill bits by hand, in a hurry, not very carefully, on a grinder with some sideways wheel vibration, and "could do better". I start at the cutting edge, and then do a "sweep", partly rotating, and partly dropping the end of the drill to "back off" the face behind the edge, a' la "conical", though it is not really a true cone.
Once I start, I complete the "sweep" in one move. Any hesitation leaves an extra flat facet. Of the two bits in the picture, the one to the right is done rather better. The left one has a not-so-good "curved" cutting edge. Both drills have been taking abusively harsh drilling into RSJ girders, and some electrical tray through a whole afternoon. Both are still cutting just fine, even though the sharpening is so casual and non-standard.
I am impressed with the other ways it is done in the links, and I am going to try these.
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How to Hand Sharpen a Twist Drill
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How to Sharpen a Drill Bit Quickly and Easily
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Using Drill Doctor To Sharpen A Drill Bit
I get it that you want to use Drill Dr, but if you go there -->
sharpen drill, you will find so many tricks and jigs, and little guides that you can make up from plywood, etc. that unless you are totally wedded to the Drill Dr. with the scored grind wheel, you might want to give some of these a try.
I would not argue with a trusty little tool that has given great results over 25 years for
@pontiac428 .
Then again, how old is your DDr? I have a beat up old WorkMate that is at least 20 years old, and despite it needs a bit of de-rust and some refurb paint job, it is quality way better than the new bits of pressed tin can that pass for "WorkMate" in the DIY store.