I’ve heard that if you substitute vodka for half the water in making pie crust, it prevents toughness..never tried it...
Chop the shortening into fine small bits, cubes perhaps 1/8th inch on a side, and use no more water than you need. When you roll out the pastry, you want those little chunks of shortening to flatten out; these will make boundaries between the pastry layers, keeping them from sticking together. Hence flakes.
A pie crust so construsted is extremely fragile. When it comes time to put it on the pie pan, roll it around a floured rolling pin then unroll it onto the pan. This enables you to transfer it without putting a finger through it. Same for the top crust.