BU2B -- This is long, but there are several good approaches.
I don't know where "we" are in our Bible reading at this point, but if the Gospels this would be a good starter on Jesus words about "the generation".
#1) I think the New Lite on the generation is a big issue right now. Why would Jehovah wait until 99 years later to give His people the "correct" understanding on what Jesus was saying? (All those who qualified as the Million Now Living Will Never Die, are in fact, DEAD.) There is lots of murmuring going on about this, esp among the older folks who did not expect to face death. Ever.
Ask if SHE knows the new understanding. Tell her you are CONFUSED about this. How can a baby, the parents, the grand-parents, and the great-grand-parents (100 years) all be "THE generation" that will not pass away?? How would she explain that to someone at the door? At work?
Ask if SHE knows that this is the 3rd (I think) adjustment since 1995 (and THAT was a big one too). When else in Bible history did Jehovah continue to give His people false information again and again and again? When did Jehovah ever "test" or "sift" His people using lies or misinformation from His prophets (or his "channel" of communication)?
Of course, it would be best if these things are not YOUR questions or concerns. They should come from someone at work/school; or an RV; or Bible Study; or very close friend who has doubts (and has sworn you to confidentiality). Or, someone in service could hand you a print out from jwfacts.com. You do NOT want her going to the Elders to seek help for you.
#2) Do you know of an Elder that was appointed while he was involved in wrongdoing? Adultery? Child abuse? Embezzlement? Then how did this individual fool the Holy Spirit? (Cong appointments are made by the Holy Spirit.) Sure, imperfect men can be fooled by such a person who is carrying on secret sins. But how do they fool Jehovah or His Holy Spirit? Thus, are these Elders REALLY appointed by GOD? (No.) Then how about those in higher position? Recent reports of COs leaving. Or Bethelites. Or Assm Hall Overseers. OMG! What about the Governing Body members? The GB was even infected with "apostate" members in the past!!! Is this happening again? What evidence do we have that they are telling us Jehovah's direction for us?
#3) Is the Good News REALLY being preached in all the inhabited earth? Then why are only 1/10th of 1% of people responding to the Good News? Doesn't the Bible tell us that the Will of God is that ALL men should be saved. Is that the best that He can do? Why did he pick such a lousy PR representative? Pick some friends or family members or neighbors that you know are REALLY good Christians. Is Jehovah REALLY going to destroy them just because they are not JWs? Aren't they better Christians than some JWs?
Even in this country where JWs are better represented, how are they doing in communicating the Good News? Do your neighbors really know what the message of JWs is? Have they received enough information to have been fairly warned that they will die? Or do they just know that JWs do not celebrate Christmas and birthdays. Or that they don't accept medical treatment (yeah, we know it's just blood transfusion, but do they?). How can we say the GN is effectively being preached if they HAVE NO IDEA what it is. JWs preaching campaign is a SHAM! They are not warning anyone about anything by leaving an old rag in the NH or HBH that doesn't get read! THIS is Jehovah's BEST?
Go slow.
These are the REAL questions that lead many to discovering TTATT.
You cannot force feed them any more than you can force feed your non-JW family members to accept The Truth(TM). They have to drink on their own. They have to discover it on their own (or think that they did). Usually a person has to be harmed personally. Sad but true. We watch and sympathize with others, but we excuse it because we don't know the whole situation. But when things happen to us personally, then we know.
Good luck,
Doc