Keeping track of every single training event they are doing or hour they are building would be a lot, but it's nice to
know the basic outline of the training your future pilot is going through – plus, I'm sure they'll appreciate you
showing some interest and knowledge of what they're putting so much effort into.
In simplest terms, they will complete 6 courses before completing their time-building phase: Private Pilot, Instrument, Commercial Single Engine, Commercial Multi-Engine, Certified Flight Instructor, and Certified Flight Instructor Instrument ratings. Each course will include an FAA written exam and a practical test known as a checkride at the end of the course.
Following their training, you can expect roughly 2 years of time-building before they are working at an airline. Time building is all the hours of flight time needed to work for an airline. Along the way, there will be a plethora of training events that may be more nerve-wracking or of higher importance in their training. Paying attention to those events your pilot mentions in conversation can be very meaningful. Whether sending a good luck text before their first solo or asking how their checkride went, showing them that you care to remember and understand the significance of their events will go a long way!
Lastly, it's essential not to deflect if you have concerns for your loved one. Discussing your biggest aviation fears with your future pilot is probably not the best way to send them into training. However, concerns are valid and should be addressed in a delicate yet appropriate manner. They have likely, and hopefully, done their fair share of research before selecting a program and feel confident in the training they are about to receive. On the other side of the coin, it's necessary that you don't want them to flight train more than they actually want to flight train. Flight training is a significant investment, and the person embarking on that journey should be doing it because they have a passion for it, not because they feel forced into it. Lines can easily be crossed without knowing it. If your loved one is training only because they feel obligated to, it can result in training failures and resentment. Support them but do not force them. They ultimately have to enjoy flight training to become a pilot.
As with most big ventures, your friends and loved ones take, it's important to be supportive of them and happy they are pursuing their goals. You don't have to be an expert on all things aviation or know every tail number of the training fleet they use, but I promise that being involved and invested in their journey will be rewarding for both of you!