The pole’s kit

Before you start anything you should put on the flagpole all the necessary equipment. Set a halyard to raise the flags (it should slide properly). Also put three shrouds on the pole. One of them will be used to raise the pole, the others are needed to keep the flag pole stable as you raise it.
Make sure you will be able to pull the shrouds down once you’re done. Use a timber hitch for example.

The hole

It is big enough to allow the pole to rotate. It is at least 1/10th the length of the pole.

Put a flat stone at the bottom and put two strong pegs in the ground. The flag pole will first come up against the pegs then slide inside the hole. (see picture 1)

The docking

You need to dock the pole tightly to the winch, in a line with the pole. You can pull the pole to the hole with the winch.

You also need to dock the flag pole so that it rotates well (see picture below).

You will then dock the two shrouds used to stabilise the pole around two stakes 120° from the hauling shroud. Make sure they are a bit loose (use a round turn, see picture 2).

The manoeuvre

The crane will be set in a line with the pole and the winch. It will be set evenly on each side of this line, making a 90° angle with the shroud-pole line.

The hauling shroud will go over the crane and will be docked to the winch. (see picture 3a). The other shrouds (not on picture 3) are held with a round turn. They should slide progressively as the pole is raised.

The winch is used as long as the crane is needed (see picture 3b).

At the end, all that’s left to do is to straighten the pole with the two lateral shrouds and the hauling shroud (see picture 4). Last but not least, pull the shrouds down and steady the pole.