I cut the strings 2 tuning posts ahead
this is the recommended standard
From the Fender Telecaster set up guide:
TUNING KEYS
How you wind the strings onto the pegs is very important, whether you're using locking, standard or vintage tuning keys. Start by loading all the strings through the bridge and then loading them onto the keys as follows:
Locking tuning keys. Picture the headcap of the neck as the face of a clock, with the top being 12:00 and the nut being 6:00. Line the six tuning machines so that the first string keyhole is set at 1:00, the second at 2:00, the third and fourth at 3:00, the fifth at 4:00, and the sixth at 5:00. Pull the strings through tautly and tighten the thumb wheel, locking the string in. Now tune to pitch.
Standard keys. To reduce string slippage at the tuning key, we recommend using a tie technique. This is done by pulling the string through the keyhole and then pulling it clockwise underneath and back over itself; creating a knot. You'll need to leave a bit of slack for the first string so you have at least two or three winds around the post. As you progress to the sixth string, you'll reduce the amount of slack and the number of winds around the keys.
Vintage keys. For these, you'll want to pre-cut the strings to achieve the proper length and desired amount of winds. Pull the sixth string (tautly, remember) to the fourth key and cut it. Pull the fifth string to the third key and cut it. Pull the fourth string between the second and first keys and cut it. Pull the third string nearly to the top of the headcap and cut it. Pull the second string about a 1/2" (13 mm) past the headcap and cut it. Finally, pull the first string 1 1/2" (38 mm) past the top of the headcap and cut it. Insert into the center hole in the tuning key, bend and crimp to a 90-degree angle, and wind neatly in a downward pattern, being careful to prevent overlapping of the strings.