I'm going to reveal my shameful secret: I can't drill holes perpendicular to my work.
I was putting bench dog holes in my bench top, and I figured I would try the trick I saw on a Youtube video. I would put a V-shaped notch in a thick batten and use it to support the bit so it cut straight. Then I realized this will not work for spade OR Forstner bits. I could have used a Silver & Deming bit, but I hate to ruin them on wood.
I got out a Craftsman gadget with two springs on it. It's supposed to hold the drill at a fixed angle to the work while you drill. Apparently it doesn't. I have one hole that looks like it's a solid 5 degrees off vertical.
So what's the answer?