Have you ever experienced someone trying to help you in a way that wasn’t all that helpful? As a new mom, this is something I experience often. Someone gives advice that’s more discouraging than helpful. Another person offers to pick me up for lunch—not realizing that having to transfer all the baby gear to her car really is more work than help. I know that people mean well, and this compels me to show them grace in the situation. But it can still be uncomfortable and frustrating.

Unfortunately, the same concept can hold true when we try to serve people in our communities. We can make people uncomfortable and frustrated—even when we’re trying to help, even when we have the best of intentions. The only way to avoid this is to get to know the people we’re serving and actually listen to what they need. Far too often, though, we begin serving by brainstorming ways we think we should help. We assume we know what others need, and that isn’t a wise way to begin serving.

The trouble is that listening takes work, humility, and time. It may include messy, uncomfortable conversations about someone’s need. It may force us to visit a dangerous neighborhood or discuss touchy topics like poverty. Even at the simplest level, there’s the awkwardness of starting a new friendship with someone who may seem different from us. And it requires us to relate to people in need, to recognize that we're not better simply because we have more.

But listening and truly getting to know the people we're trying to serve make all the difference. Listening leads us to help in the ways that would be most helpful—not the ways that make most sense to us or are easiest for us.

My small group learned the hard way that what we assume others need doesn't always align with their true needs. We became aware of a mother and two children who were on the cusp of homelessness. Our immediate assumption was that they needed help with their rent, and we considered sending money to help with the expense. One woman in our group, though, had spent time building a relationship with the woman, and she knew that sending money wasn't the answer. She knew that the woman really needed friends more than a simple handout.

After listening to her real needs, we decided to bring over groceries and spend time with her and her girls. We didn't realize how special this was until we met her 9-year-old daughter, who has a severe physical condition that has left her unable to walk or sit on her own. She also can't speak. Because people aren't sure how to act toward this young girl, many just look away, which leaves the mother heartbroken.

When we chose to bring groceries and actually spend time with this family, we met a deeper need: the need for dignity and friendship. It's something that sending money for rent simply couldn't have done.

Listening is the difference between assuming we know best and trusting that others know what they need. It's the difference between having good intentions and actually serving people in the ways they need to be served. It's the difference between offering a handout from our pedestals and rubbing elbows with friends.

Listening led to my friend's idea to organize a Halloween party for a local homeless shelter. Two years ago, Heather dropped off backpacks and school supplies to the homeless shelter after reading about the need at her church. Most people just drop off their donations at the church, which, although helpful, removes them from the reality of helping another person. Instead, Heather drove to the homeless shelter to drop off her donations.

For the first time, she realized that it was only five miles from her home. As she toured the transitional living center for families at the shelter, she had a difficult time wrapping her mind around the idea that there were mothers with young children—children that were so much like her own—in such need so close to home. Seeing whole families living in small dorm rooms changed something in her, and she was compelled to act.

After talking with some people, she realized that the kids living there couldn’t trick-or-treat because the neighborhood was unsafe. Plus, they didn’t have costumes to wear trick-or-treating or to their school Halloween parties. So she decided to throw a Halloween party for the families, providing costumes for all the children.

“Every year they're going to school, and no one has a costume. Imagine being that kid. That's the part that kills me,” she said. “They're so marginalized anyway, and to be left out of any kind of celebratory thing…Everyone does Christmas, and a lot of people just don't think about Halloween. But Halloween is such a great time for kids because you can be anything you want to be. That's my favorite part because they need hope.”

The first year was chaotic. No one had done this before, and Heather wasn't sure how to prepare. In just over a month, she gathered enough costumes to serve 40 kids and enough candy to keep them happy for a long time. She and a group of volunteers also fed nearly 100 people at the party with hot dogs that a couponing friend had gathered.

The party started with two hours of the volunteers playing with the kids and helping them find the perfect costume. This allowed the moms some much-appreciated alone time, time that they rarely get to enjoy. Then everyone gathered for a family mealtime, followed by fun games.

Heather's favorite moment of that first year came when her friend, who volunteered at the party and brought her fifth-grade son, told Heather about their experience. She told Heather that after the party, she'd asked her son what he thought about hanging out with the children who lived at a homeless shelter. The son responded in disbelief: “Mom, none of the kids could have lived in that homeless shelter! We were all just hanging out!”

After a chaotic yet successful first year, Heather had an even bigger vision for the next year. As her relationships grew with the women and children living in the center, she realized just how much the party had meant to them. The mothers got a few hours free from their children to relax. The kids got costumes that provided them dignity at their school parties. Everyone got a fun night to forget about their difficult living situation. More than that, the party showed these families that there were seen and important. And that meant so much to Heather.

Through tears, Heather told me, “There are endless possibilities for helping. They have nothing. More than anything, they just need people to believe in them. For someone to let them know they have worth.”

With much more time to prepare for the second year, Heather and her friends gathered enough donations to costume 85 kids and enough candy not only for the party, but also to allow trick-or-treating on Halloween. Rather than send the kids out into the unsafe neighborhood, the staff at the center offered candy as the kids trick-or-treated from office to office.

But the party was much more than costumes and candy. It also included a station where a volunteer talked to the kids one-on-one. After getting to know them a little and hearing about their interests and dreams, she would speak goodness into their lives. To one she would say, “I see medical school in your future.” To another, “You're going to be a successful scientist.” She named something valuable within the children, and it was clear that they were touched. Maybe for the first time in their lives, someone had listened to them and told them they had worth and a future.

As Heather left the party last year, the director asked, “How are you going to top this? Have the next party on the moon?” Heather agreed that was the only way to top it, so this year’s theme is the moon. The party will involve a moonwalk bounce house, space-theme decorations, and even “space ball” sandwiches.

Some have pushed back at the idea of throwing a Halloween party, but Heather stands behind the parties. Rather than decide what the families needed, Heather listened. Now they get to celebrate a huge cultural holiday, participate in their school parties, and enjoy a night filled with possibility about who they could be in life.

As she further developed relationships with the families at the center, Heather learned that the children didn’t have any books. So she set to work building a library for the center where both kids and parents can borrow books. She also helped to find volunteers to read with the children to help them improve their reading levels. After learning that many of the moms struggle with reading, Heather’s now trying to find a way to help the women with their literacy.

Heather is passionate about the women and children living at the transitional living center. She deeply loves people, and her faith compels her to help in any way she can. Loving on these families—and even the director, who has become Heather’s friend—is natural for Heather, and these relationships have led to natural opportunities to serve.

It comes so naturally to her that it was actually hard for her to articulate how it all got started and how the new ideas came about. Her serving is a natural extension of her relationships with these women and children. And that is a lesson for all of us. Serving should not be simply a means to evangelize. Instead, it should be the natural extension of our relationships with others—people we care deeply for. People we care about enough that we’re willing to listen for their real needs in order to serve them in meaningful ways.

When we’re focused on loving others, listening and serving come more naturally. People are able to see glimpses of God’s deep love. They understand how his good news really could be good news. They get to see, as Heather puts it, that God’s love is for them.

Rather than expect others to show us grace and see our good intentions through our sometimes not-so-helpful service, let's give the grace of listening and really get to know the people we want to serve.

Amy Jackson is managing editor of Gifted for Leadership, SmallGroups.com, and ChristianBibleStudies.com. You can follow her on Twitter @AmyKJackson.