If your bike is like a road bike, it will have the presta valve. Therefore, it might have a lock washer that holds the valve in place with the rim. Some riders don't use that lock washer. But most good inner tube makers include the lock washer as part of the tube.

Sometimes the pump head won't go far enough onto the presta valve. But if you remove the lock washer, it gets the required distance. After inflation, I replace that lock washer back onto the valve and tightened onto the rim.

When inflating at home, I always push down on the presta valve to let out some air to clear out any debris that may be stuck in the presta valve. Then I will know that during inflation, the tire will get air in.

Technique: for big guys, there is no technique. They just push down on the pump handle to inflate. But for me, its different. I rely on leg power more than arm power. And because of that, its better. Once you get to around 70 lbs of pressure on the gauge, the resistance is greater. That's when you need to keep the elbows locked in and use the body weight to push down on the handle, at the same time bending the knees as if you're doing squats with free weights. Its not a slow motion pumping action. Its a deliberate quick motion downward. Like a quick snap.

Same goes for Topeak Road morph. Taller guys won't be able to do this easily. They still use arm power to muscle their way thru this.