I want to cut a hole in my desk (3/4" furniture grade plywood with an oak veneer) to run cables through. I'll be using a hole saw and my cordless drill. Since this is going to be very visible, I want to be sure that the hole is perfectly vertical, and that I get it right on the first try.

How can I ensure that the drill is angled correctly? Should I even be trying this with a hand-held drill? If not, what tools should I think about using?

  • Won't the edge of the plywood also be visible? I used woodcraft.com/Product/149803/… in a similar situation, which makes the verticalness less critical.
    – SqlACID
    Mar 24, 2015 at 11:39
  • 6
    Realistically, nobody will notice if the hole is off a few degrees.
    – keshlam
    May 15, 2015 at 2:51
  • 2
    I would also consider a desk grommet. It will look better than just a hole and will also hide some issues that could develop from this type of project.
    – Dano0430
    Nov 23, 2015 at 14:04
  • The trim or grommet is more important than the hole for looks.
    – NipFu
    Feb 24, 2016 at 7:05

8 Answers 8


I saw a video online, that suggested a simple jig that will allow you to drill straight into a relatively flat surface.

Take a piece of stock that is square. From the end of the stock, cut a wedge section that is 90° in the wedge (the left inner face should be 90° from the right inner face) and the wedge vertex (the line in the middle of the removed area), should also be 90° from the bottom face of the block.

Place the jig flat against the surface you want to drill, snug the drill bit up to the inner corner (the cut out area), and drill away.

You may need to make several of these to accommodate different sized bits.

To allow for a forstner bit, cut a section from the bottom of the jig (see the side view image) allowing just enough clearance for the bit.

It is possible to make this jig with the vertex at a different angle. You can make the jig as above to get a perfectly square reference. Then run the bottom plane of the jig through a table saw (or whatever you have that will work) to shave an angled wedge from the bottom.

enter image description here

Simple Drill Straight Jig - top view

Simple Drill Straight Jig - side view

The notch has been removed in the side view to allow for a forstner (or similar) bit to have clearance.

  • This solution will work excellent for simple straight drill bit applications. Not so good for hole saw or forstner bit usage. Mar 18, 2015 at 14:44
  • I have been thinking about that. You could cut a section away from the bottom face to give room for either of those bits. I'll update the drawing when I get the time. Mar 18, 2015 at 15:46
  • Oh wow! I need to run a forstner bit without my drill press, because the work piece is too wide to fit into the press. This is going to save my life. (Or at least my project!) May 6, 2015 at 5:27
  • I updated the post with a link of a video that actually talks about that jig you refered to.
    – Matt
    May 14, 2015 at 19:27
  • @Matt While Izzy Swan covers a similar jig, the video I saw was from someone from England. May 14, 2015 at 19:29

In two words: Pilot hole

If you have a drill with the handy leveling bubble, this can be handy. Otherwise line up your drill bit using something akin to a speed square or carpenters square (checking more than 1 axis), then drill your pilot hole. Not only is the pilot hole beneficial, but I find it makes your accustomed to what arrangement/direction you will be drilling.

This will help most if you are using the kind of pilot hole with a center drill bit that protrudes from the barrel/shank.

Otherwise, they do make a jig of sorts that bolts to your handheld drill and provides a guide and baseplate. The creates a pseudo drill press-like device.

  • 4
    As an added bonus, if you determine that the pilot hole is not vertical enough, you can drill another one very close by, and let the final hole engulf them both.
    – FreeMan
    Mar 17, 2015 at 19:05
  • I have done this SEVERAL times, although was not ready to admit it. Nice addition @FreeMan Mar 17, 2015 at 19:13
  • Who is to say you could not make the pilot hole with a drill press, assuming one was available, so that it could then be used with a handheld ( at least for 90 degress )
    – Matt
    Mar 20, 2015 at 1:17

A drill guide will help you maintain the required angle, in your case, 90 degrees perpendicular to the desk. These are readily available at your local home improvement or tool store.

Drill Guide http://www.homedepot.com/catalog/productImages/400/05/05534eb7-0230-4b1d-9f68-f9297f412a6f_400.jpg

  • 3
    I bought one of these years ago and have to say i was more than under whelmed. I had a number of problems including - a) Getting the thing set square - b) Getting it to stay square - c) Making the drill difficult to handle with this 14" long thing hanging off its front - d) Being completely useless in tighter spaces. Mar 18, 2015 at 14:50
  • 1
    Every single drill guide like this that I've seen is incredibly flimsy and nearly worse than useless. I think the only time I'd use a drill guide like this is when I need to drill mostly straight holes through timbers for putting bolts or lag screws in, for heavy framing. I would not rely on this style of guide for furniture grade anything.
    – William S.
    Mar 21, 2015 at 7:24

I saw an ad on a woodworking site and I was reminded of this question. These were touched on in other answers but I wanted to add something more concrete with a picture as an aid. The following is a picture of a drill guide. This would be used with your regular powered hand drill.

Big Gator drill guide

You can see that the underside has 45 degree angle to as so you could also use this for drilling on square corners and even on the surface of a cylinder.

This would have the advantage of being compact, reliable and reusable. I am not aware of any other manufacturers but i'm sure they are out there. The site where that picture came from is: Big Gator Tools

There are also called "Drill and Tap Guide Blocks"

Cheap like me?

Wont last as long but it would be real easy to make a facsimile of this with some scrap and a drill press.

  • I have these, they are worth every penny. They go great with drill stops. They're one of my most used tools. With the 45 degree bottom you can use them for drilling into cylinders, too.
    – Jason C
    Nov 22, 2015 at 21:28

Just get it close to vertical, and add in a cable grommet. With these you can be about 1/8" off in the hole size, and angled like a drunken monkey drilled it, and it still looks great.

enter image description here

  • 2
    As a responsible pet owner, you should always keep your monkey away from alcohol and power tools!
    – Doresoom
    Jun 8, 2015 at 14:36

I think I'd try making a guide block by drilling a through-hole into a piece of thick stock at the drill press. Use the same bit you plan to drill into your desk with. Next, locate the block on the desk where you want the hole (registration marks might help with this) and clamp or double-stick tape it in place. Use the hole in the block as a guide sleeve for your bit as you drill into the desk. Should work fine for any bit you can chuck into your drill press. The thickness of the block will limit your depth of cut, but once the hole is well started you should be able to remove the block and use the hole itself as a guide if you need to drill further.

  • 2
    I should add that you might want to - if it's possible - clamp a backer board of some kind to the underside of the desk. Will prevent the surface from splintering and breaking out when the drill comes through. - Steve S. Mar 22, 2015 at 14:41

Usually the cutting face of a hole saw is enough to give a good reference for verticality. If you're really concerned, google "portable drill guide" for some products that can help.

This won't work well with hole saws, but if you're using a simple twist bit, auger bit, etc. you can put two squares on the desktop at 90° apart as a visual reference.


Mount a bull's eye level on the back of the drill.
Requires setup once.


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