Many of us have experienced this situation – whether as a parent making the request or as a neighbor, family member, or friend hearing the sales pitch.

My kid’s (insert a team, club, activity here) is selling (candy, cookie dough, wrapping paper, bed mattresses) to raise funds (for a trip, new equipment, etc).

Can you assist by paying significantly more than the actual value of the item so that a fraction goes to our team, allowing my child to earn a prize that they likely won’t care about in a few weeks?

Welcome back to Uncomfortable Conversations About Money, a series where we explore difficult subjects or situations related to money that can make you uneasy. We’ll discuss the issue and offer some practical solutions.

Would You Like to Make a Purchase?

The challenge: Yes, I used a bit of sarcasm there, but many of us are familiar with this constant request. As parents, we often feel guilty bringing in the order form to work or posting about it online. Sometimes we push our kids to go door-to-door or take the order form to gatherings with friends and family to politely ask for support.

Let me be clear: these fundraising activities often support significant projects. A colleague mentioned that she didn’t want to undermine the importance of some of these initiatives. One fundraiser she knew of helped to preserve Native Hawaiian culture, a cause in dire need of additional support.

However, it’s also true that these fundraisers can accumulate and put pressure on your finances.

So how can parents manage years of these fund-raising efforts for their children, especially when juggling multiple kids, various activities, and limited friends and family who can help?

And what about those friends and family members on the receiving end? How can they politely decline or limit their purchases without looking stingy?

Set Your Priorities

The recommendation: The expert this month is Julie Williams, a certified financial planner with WealthSpire Advisors in Delafield, Wisconsin. She’s also the mother of an adult son with plenty of fundraising requests and married to a high school teacher who receives numerous requests from various fundraisers.

Williams advised that she and her husband encouraged their son to select just one or two teams or organizations that mattered most to him for fundraising efforts.

“This way, we weren’t making everyone ask for every little thing,” Williams explained. “It helped us remain focused. If he didn’t show enthusiasm, then why should I? They provided all the information for the parents, but if he wasn’t keen on fundraising, I shouldn’t push it for him.”

Williams also insisted that her son do the asking himself. If he wanted to visit her workplace, she would bring him along.

“We helped him prepare a little script outlining what he was asking, why he needed support, and what the funds would be used for,” she shared.

According to Williams, this experience equipped her son with the skills needed to communicate effectively with adults and handle rejection gracefully.

“Now as a 24-year-old, he approaches individuals confidently, maintains eye contact, and presents a clear reason for his request. Even when someone declines, he knows how to respond graciously, thanking them for considering his request,” she added.

You Can’t Say Yes to Everyone

Regarding the constant pitches they receive from friends, family, and students, Williams stated that she and her husband operate on a first-come, first-served basis.

“My spouse works in education, so it’s not unusual for us to get that question. Each student wants something from their teachers,” she explained. “In our family, the rule is that whoever asks first gets what they want, which prevents us from feeling guilty about declining requests or having to pick and choose who to say yes to.”

According to Williams, they might occasionally get a second box of cookies if the request comes after the first box is finished. Yet, they usually adhere to this guideline.

“As much as we want to help, we can’t afford to agree to every request and still meet our own personal goals,” she noted.

Williams recommends setting a budget for fundraising activities related to children, such as those involving kids, grandkids, nieces, nephews, and neighbors.

Another suggestion is to limit support to one event per child, which encourages them to define what matters most to them, she said.

What’s a polite way to decline?

There are always polite ways to turn down such requests. Williams shares some thoughtful ways to say no: “Thank you for reaching out. I appreciate your efforts, but I’m unable to support that financially at the moment, or I’ve committed my support to another cause already.”

Receiving a “no” can also serve as a valuable lesson for the child, according to Williams.

“Learning to accept no as an answer is crucial, as is knowing how to say no,” she stated. “If they witness an adult gracefully saying no, it sets a great example for them when they face similar requests.”

Advice for parents

Lastly, Williams reminded parents to avoid feeling pressured into fundraising for their children.

“We need to be selective about where we allocate our support,” she emphasized. “It’s important to pick our battles.”

We want to hear from you

Do you have a topic related to uncomfortable money conversations that you’d like to propose? Or would you like to share your experience in a feature story? Please email blinfisher@USATODAY.com and include “Uncomfortable Conversations” in the subject line.

Here are some upcoming discussion topics. Would you like to share your uncomfortable experience regarding them?

Have you lent money to a friend or covered their expenses with the expectation of repayment, but have yet to see it returned? Has that affected your friendship?

Did you receive a holiday gift from someone when you weren’t prepared to give one in return? How did you feel, and what actions did you take?

What’s your response when your partner’s ex requests financial help?