The holidays may be a difficult time to bring up tough topics with aging parents – such as advance medical directives, living wills, assisted versus independent living arrangements, end-of-life wishes, naming a legal and medical proxy.

But healthcare experts and aging welfare advocates say there may never be a better time than the winter holidays to start exploring these topics with their loved ones.

It’s also a good time for adult children to catch up with parents, gather some information on health and legal matters, and to see how they are managing their affairs.

“During the holidays, while family members are together enjoying one another’s company over good food, take a look around. Observe how mom and dad are doing,” says author and caregiver expert Brenda Avadian.

“Are they participating in the conversation, or remaining quiet? Does their home appear neglected? Are they keeping up with their bills?”

If they’re healthy, alert, still driving a car, and otherwise living on their own, it might be premature to start discussing estate planning or end-of-life wishes.

But if it’s become evident that their physical or mental capabilities are clearly declining, or they’ve had mounting, chronic medical issues that can’t be ignored, it might be time to start considering having that conversation with them, says Avadian.

Here are some strategies that can help you do so with sincerity and sensitivity.

Put parents at ease: Gauge how open and receptive they are to talking, and remember that cornering or confronting a parent is not the way to go about it. Segue into the some of the topics you’d like to chat about by putting yourself in their position; it’s a constructive conversation starter that avoids putting them on the defensive.

“Talking to your parents about your personal legal documents and how you are planning to update them this year will make your parents feel that the conversation is not about them,” says Kathryn Bennett of The Memory Center. “Casually ask your parents when the last time they reviewed their legal documents was and if they would like to update their paperwork as well.”

“It’s not always easy to broach these topics, and sometimes, people are resistant when you do,” adds Ruth Drew, director of information and support services for the Alzheimer's Association. “It’s good to just start the conversation, ‘You know, Mom, I’ve been updating my will and talking to my lawyer about my power of attorney, and if I wasn’t able to speak for myself, I wasn’t sure what you and Dad would want. How do you want to handle that? Would you want to be willing to work on that sometime?’”

Anticipate reluctance: Be prepared for a negative reaction. Sometimes changes in personality with age or other health issues can get in the way.

For author and caregiver Alexandra Allred, her mother’s Alzheimer’s disease and father’s dementia made discussing sensitive topics difficult.

“Our parents were so paranoid, that any time we tried to broach a subject in any way, we’d get, ‘We’re good from here, we’ll take care of this.’ That’s where our struggle really was,” she says.

This can make the process that much more difficult – mental lapses in a dementia or Alzheimer’s patient might mean not remembering key facts, names or phone numbers, but pride or denial might stand in the way of a transparent conversation.

“They’re so independent, and such great critical thinkers, they think, ‘What happened? How did I get lost?’ They do their best to cover it up,” says Allred. “Many times, they’re just aware enough to think, ‘I’m going to be put in a home.’ That’s a huge fear.”

Foster a family effort: The holidays offer a chance to get other family members on board, especially siblings and relatives who may live far away or be hard to get a hold of other times of the year.

Rallying together as a family sends the message that everyone cares about their parents’ wellbeing.

“This isn’t a single person event,” Allred says. “Unless you’re an older child, and there are aunts, uncles and cousins, you need the whole family involved. You’ve got to have a team for the physical and emotional care for the loved one. You also need to tackle backup tasks, like their car and utilities.”

Allred even suggests making a New Year’s resolution out of it – to take care of each other, to sit down and determine who handles what.

“You kind of go around the table, and if you’re really lucky, your elderly parents go along with it,” she says. “You still need to come together as a family, because this is something that can shatter a family more than the [parent’s] illness.”

Give the gift of help: Consider using Christmas or Hanukkah as a chance to make caregiving a gift.

“Instead of giving a present to your parent that will be thrown away or never used, pay for a consultation with an elder law attorney to have their legal documents reviewed,” says Bennett of The Memory Center.

One reason a parent may resist or try to refuse care from family members is not knowing how to reciprocate. Bennett says to offer a compromise.

“Explain to your parents that the best present they can give you is knowing what their plan and wishes are and having them documented,” she says. “Letting them know that will make you feel better if you are prepared.”