When the part of the skewer that is in the pot is darker colored then there is enough moisture. I wait until about 2 on a scale of 1 to 10 to water small cuttings, maybe 3 or 4  when the plant is larger and has established a good root system.

I checked out the garden section today, at walmart and they had water checkers, 3 indicators for 2.85, they looked cheaply made of course, but if you are worried about a particular cutting you don't want to over-water they might be worth it. I read the instructions and you basically have to leave the water checker rod in the soil at all times. If I were to use them I would transplant it with the cutting, because it needs to be near the roots to get a good reading. Plus you wouldn't want to disturb the roots of already planted cuttings. 

There are several different types of moisture meters out there.  I have several and use all types.  I've lost trees in the past due to a lack of water winterizing trees inside a garage.  Since using moisture meters, I have lost no trees.  To me, it best to have one and know if the soil either moist or wet.  Lowes, HD and other hardware stores carry some of the best varieties.  Walmart sells cheap gardening stuff but you get what you pay for.   I don't mind paying 10 to 20 bucks for a very good tool.  That's just me.

That's a good tip Dennis .

Austin

I think it more effective to pull your "skewer" out of the soil immediately and look to see if any soil sticks to it. If so, it is moist and does not need more water. The easiest thing thing to use is a popsicle stick, the plastic plant label or even a pencil.

That is probably a better way Barry, I have not done it for a long time but wondered if the skewer could eventually become discolored. I used to also touch it to my wrist or even lips (please don't judge me:) to feel for moisture.