The Art of Asking: How Smart Leaders Match Skills to Community Needs

I've been thinking about a conversation I had recently with Eric Winters, the founder of Heylo, about community leadership, and it's stuck with me.
We were discussing something I've observed across so many communities: people recognize they're growing in the inner rings of your community when they're contributing more.
This creates what I recognize as a contribution paradox.
As leaders, we desperately need help.
But we often approach this need in ways that create resentment rather than belonging.

The Burden of Constant Hosting

Let me share something personal that illustrates this principle.
When someone invites me to dinner at their home, I don't want to cater their event.
I host over 50 events a year, actually, that's conservative. We're hosting two dinner parties just this week.
When you invite me to your house, I want to enjoy a meal and connect with people.
This isn't laziness.
It's recognition that everyone has different capacities and seasons of life.
Some months, I may practice a certain recipe and would love to bring something I’m playing with.
Other months, I'm traveling across time zones and barely keeping my head in the time zone.
The host’s wisdom shows in the asking: 
"Is there something you'd like to bring?" 
rather than assigning: "Please bring dessert."
That shift changes the relationship.

The Freedom to Decline

Here's rule one of healthy community engagement: freedom to say yes or no.
This freedom matters in part because life is complex.
People get tired.
Kids get sick.
Someone just flew in from another timezone.
When we create cultures where people feel they must "tow their own weight" regardless of what's happening in their lives, we're not offering an easy way for them to participate in connection time.
We're building obligation systems that can breed quiet resentment.
The most sustainable communities understand that contribution should enhance someone's life and participation, not add to their burden.

The Matching Exercise

During our conversation, we talked about what he called "the matching exercise."
This isn't random delegation, the thing that makes every community leader cringe.
You know the moment: "Hey, Charles, maybe you can do the social media."
The polite response: "I really don't want to do that."
The matching exercise is different.
It's intentional recognition of what people are naturally good at and actually enjoy doing.
Take the running club example we discussed.
Instead of: "Hey, Charles, we need someone to sweep tonight to make sure no runners get left behind."
Try: "Hey, Charles, I'd love for you to help us with the sweep tonight. We've seen how great you are with people and how people really connect with you in this community. That would be really valuable."

The second approach isn't just looking for a warm body to fill a role.
It's recognizing contribution as an extension of someone's natural gifts and participation.
It acknowledges their already existing contribution.

The Sophistication Test

Here's a diagnostic question every community leader should ask: If nobody wants to contribute to your event, are you picking something too sophisticated?
Sometimes the answer isn't better delegation.
Sometimes it's meeting at a trailhead instead of hosting a complex dinner party.
Sometimes it's gathering at a beach instead of organizing an elaborate fundraiser.
Let’s not impress people with organizational skills.
Let’s create meaningful connection opportunities with sustainable effort.

Reading the Room

As you continue hosting, you start identifying what people are into.
You can notice with genuine interest and care.
You notice who lights up about food preparation.
You observe who naturally takes charge when technical problems arise.
You see who asks thoughtful questions that help others think more deeply.
These observations become the foundation for meaningful invitations to contribute.
During our conversation, my friend mentioned how they'd learned not to ask me to bring something because cooking all the time wouldn't be relaxing for me.
But asking me to lead a prompt as we sit down for dinner?
That's really easy for me.
That's a matching exercise in action.

The Invitation vs. Assignment

There's a world of difference between an invitation and an assignment.
An invitation recognizes someone's capacity and interest.
An assignment fills an organizational need.
Invitations create ownership.
Assignments can unwillingly burden with obligation.
When someone feels invited rather than assigned, they're more likely to bring their best generosity to the contribution.
They're also more likely to say yes to future opportunities.

Building Sustainable Systems

The most successful communities I've observed operate on a principle of distributed leadership that respects individual capacity.
They understand that some people are in seasons of high contribution.
Others are in seasons of receiving.
Both are necessary for healthy community dynamics.
We must create systems where people can contribute meaningfully without burning out.
This needs leaders who pay attention to the whole person, not just their use to the organization.

The Long Game

Community building is a long game.
The person who can't contribute much this month might become your most valuable leader next year.
The individual who seems to only attend events might be providing a crucial social connection for others.
The quiet member who rarely speaks might be the person everyone feels safest around.
When we create cultures that honor different types of contribution and different seasons of capacity, we're building for sustainability.

Practical Implementation

Start with these questions:
What are people naturally good at?
What do they enjoy doing?
What does their current season of life look like?
What would feel like an opportunity to them rather than a burden?
Then, when you need help, frame your request as recognition rather than desperation.
"I've noticed you're really good at..." rather than "We need someone to..."

The Ripple Effect

When people feel truly seen and appropriately invited to contribute, something beautiful happens.
They don't just fulfill their role.
They often lean into it.
They bring creativity and ownership to their contribution.
They start looking for other ways to help.
This is how healthy communities can grow, not through guilt or obligation, but through recognition and invitation.

Get free resources on building the community you long for at www.charlesvogl.com

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