My first year out of college, my company had a holiday gifting program in which we could adopt a family for Christmas. It was through an organization that had collected real kids’ letters to Santa, and asked people to fulfill their gift requests.

The six-year-old boy I randomly chose wanted warm clothes for winter. That’s what he asked Santa for. Not X-Box, Legos or a big shiny toy.

He wanted mittens and snowpants.

Lacking much of an income, I asked my roommate to go in on the donation with me. We had a field day together in Old Navy: Winter coat, snow pants, boots, mittens, a hat, cool jeans and long sleeve shirts. Then we picked up faux-diamond studs for the boy’s mom. We thought he should see Santa taking good care of her too.

I FedExed the package, and had to leave a phone number on the mailing slip in case FedEx couldn’t find the address. What I didn’t expect was the mom to call me.

I’ll never forget the voicemail she left on my office landline. It was clear she had just opened the package and was overwhelmed with how much Santa would give her son that year. She thanked me over and over. And she loved the earrings.

Thirteen years later, I’m still making sure I help others during the holidays. But I really want my kids (age 5 and 3) to take part.

So when I bring it up at the dinner table, here are the questions I know I’ll get:

Can we buy ourselves presents too?

Can I get them a _______ (fill in whatever off-the-wall thing my son wants)?

Why can’t Santa just give them presents?

This last one is the trickiest.

How will I answer? I’ll explain that Santa brings gifts to everyone, but sometimes parents can’t. So we need to help these parents provide gifts for their kids. For the toy drive, I’ll aim to choose children who are the same ages as mine – and try to get my children to shop for these kids.

“She likes art projects. So do you. What do you think she should have?”

“He loves race cars. Which race track should we get him?”

Hopefully they’ll identify with the kids more and get excited about how they can help.

It won’t be seamless. But it will be important. And hopefully–in 30+ years–my kids will be doing this with their kids every holiday season.

Katie Bugbee is the senior managing editor and resident parenting expert of Care.com. A busy working mother of two, she’s an expert on many parenting dilemmas, from appeasing picky eaters to finding the perfect babysitter.