touch the tip of the solder where the iron meets the pad or the pin
try to get as much contact with both the pad as the pin as you can
the pad could be dirty or not hot enough. Especially when the pad is connected to a ground or power plane layer in the PCB it may take longer than expected to reach a sufficient temperature. Usually adding some flux helps remove any dirt.
Both, which is why conical tips suck. They make poor contact with the pin and pad. With a chisel tip you make good contact with the pin and pad
You add some solder to the tip, then drag it across the pin and pad. Solder flows towards heat and if the joint is properly heated the solder should flow beautifully.
Sometimes the pad isn't heated (probably because the conical tip isn't heating it) and doesn't want to stick to the pad. It can also be due to oxidation on the joint surface. Add some flux to the surface and try again, allowing the iron to melt and activate the flux.
1 if all parts are hot, it shouldn't matter. As soon as you touch anything with the solder, it should distribute evenly around the pad and component.
2 you just feed it into the joint
If you are not quick enough, the flux in the solder evaporates and it becomes sticky. At this point, clean it and start fresh. Other possibility is that you didn't heat part and component enough for the solder to flow