Questions to Ask Your Grown Children: Understanding How You Can Help Financially

Questions to Ask Your Grown Children: Understanding How You Can Help Financially

As we are well into the holiday season, it’s a natural time to reflect on what we’re grateful for, but it’s also a valuable opportunity for families to gather and have meaningful conversations that might not happen otherwise. One of those conversations we encourage clients to consider is around financial support for their adult children.

Front-Loading Your Legacy

At Van Leeuwen & Company, we often talk with clients about how to proactively open the door to these discussions across generations. If you’re in a position to gift or support your children financially, the holidays present a perfect time to think about how you might do that in a thoughtful and strategic way.

Rather than waiting for the instructions in your will to play out someday, consider whether you have the ability and desire to begin gifting more generously now. Think of it as "front-loading" your legacy. If you're already planning to leave money to your children in the future, why not find ways to help them today, when it could make a real difference in their lives—and while you can enjoy seeing the impact your support has?

Whether it's helping with a home project, funding a grandchild’s education, or supporting a business idea, we want clients to think about how their generosity could align with what matters most to their children. There's joy in witnessing their success and knowing you played a part in it.

Family Meetings: A Practical Way to Begin

We understand these conversations can be sensitive or even uncomfortable. That’s why we often suggest hosting a family meeting around the holidays. It doesn't have to be formal or intimidating, but it can create space for intentional dialogue. In fact, many of our clients have found that talking about financial support in a clear and transparent way actually brings their family closer together.

A few useful prompts we recommend trying that don’t create a sense of pressure or a financial “audit”:

  1. What’s something you’re very excited about this year?
  2. Are there any goals or opportunities you’re working toward?
  3. Are there any areas where things are tight and more resources would open a meaningful
    door?
  4. “Your mom/dad and I would love to use some of our extra resources to help open doors
    and invest in your family, but we don't want to overstep. Are there any areas where more
    financial resources would really help your family?”

Some parents also appreciate seeing how their children use gifted funds. Whether the money goes toward savings, education, or something meaningful, it offers insight into their children's priorities, and it may even influence how and when they continue to give.

The Takeaway

If you're fortunate enough to be in a position to help, now may be the time to start that conversation. These moments of family connection can lead to clarity, mutual understanding, and a stronger financial foundation for the next generation.

And remember, your generosity doesn't just provide support but also creates a legacy you can witness in real time.


Securities and advisory services offered through LPL Financial, a registered investment advisor, Member FINRA/SIPC.

This information is not intended to be a substitute for specific individualized tax advice. We suggest that you discuss your specific tax issues with a qualified tax advisor.