How to Connect With a Skeptic
Why logic alone rarely moves people — and what skeptics are actually asking for instead.
It was one of the most monstrous rains I’ve experienced and we were crammed like sardines under a tiny tent originally meant to shield neighborhood kids from the scorching pre-memorial day heat.
We were together for a “front-lawn hop” where newer neighbors could meet those who had lived on the street for years, some as long as 60 years! Between laughter and buckets of rain, several neighbors chatted about the new Accessory Dwelling Unit (ADU) and multi-family dwelling laws our councilman was spearheading for the city at large.
“You know parking is going to be trash, and the neighborhood is really going to suffer with what he’s proposing.”
“Why can’t we get the investment some of these other neighborhoods are getting... share the wealth, ya know?”
“Main street is dismal, everything’s closing down, why can’t they focus on that?!”
My mind went to an equally rainy day a month earlier, when I’d chatted with our councilman after he’d been caught in a storm on his bike commute.
He shared about his teams goals to create affordable housing, opportunities for homeowners as incomes are increasingly stretched, and economic opportunities for local businesses. I could tell how frustrated he was, working on and lobbying for these initiatives that directly reflection of what neighbors are asking for, but still facing a disconnect that seems unpassable.
I felt for him because I walk through the world in a similar way; there are so many causes and possibilities I care about, and every missed opportunity to unite with friends and family weighs heavy on me.
There are so many explanations we reach for when people don’t see what we see, and unfortunately, they’re not explanations that help you connect with difference, or those outside your circle.
“People make decisions based on logic.”
Many of the leaders I work with start from this place, from the belief that if they could perfect the pitch, sharpen their asks, or close the room perfectly, the room would flip.
My team hears the same from those looking to connect with investors; if they left fewer objections unaddressed, or could just tighten their storytelling, they’d have the buy in they need. This worldview feels true because pitch moments do matter, often a lot, and that creates a reinforcing loop: when it works, it feels like mastery of messaging; when it doesn’t, it feels like the logic wasn’t sharp enough yet.
In many contexts, it’s a mistake to treat any room as one mind, as a single decision-maker. You’re dealing with a tapestry of minds with different psychological needs.
Is it actually messaging or logic in the way?
Or is it the emotions that come with a change or the choice?
How did you make space for that as you shared?
Underneath the reasoning, there is often something more human at work and when those needs aren’t met early, logic rarely lands on its own.
“They are simply against what we’re for.”
Some of your most valuable allies begin as (and will always be) skeptics.
Treating them as your opposition can push away exactly what could strengthen a movement. The thing to remember about skeptics is that many are actually in favor of the same outcomes, but disagree about methods, priorities, or risks; likewise, their uncomfortable questions and zeal for testing your assumptions are something I’d compare to a bid for connection.
That may feel like a stretch, but hear me out:
Yes, in some cases questions serve as a defense of their space, ideology, community, etc., but pushback is a bid for connection that says, “Help me understand where I fit in this. Help me trust that my concerns matter.”
I saw a version of this in a town hall redesign process &Human worked on for a stalled river dam project. On paper, the expertise was solid. The intent was sound. But residents were brought into the process far too late.
In one case, a community member learned about the project only when a surveyor was on their land, the result of a misunderstanding about where public and private boundaries actually sat. That moment became the entry point into a much larger realization: a historic landmark they had deep emotional ties to might be removed.
Rumors moved into the space where information should have been.
By the time leaders were ready to share more clearly, too much time had passed. Trust had already begun to erode. You can read more about how we rebuilt that trust here. I don’t doubt that many members of the community are flatly against the project as a whole, and not people who could be won over, but I can’t help but wonder what might have been possible:
Time saved, better plans, fewer costly revisions — opportunities left on the table without the voices of skeptics.
The friction of difference is often the place where the strongest ideas get sharpened.
“If they just understood the stakes, they would care.”
Care is a funny thing.
It’s easy to assume you know what people care about, and easier still to skip the crucial step of understanding what’s important to them.
The old saying gets repeated so often it’s easy to dismiss: people don’t care how much you know until they know how much you care.
I see versions of this play out all the time, and it’s sort of what I just described within our river project example: Community members, employees, donors, residents, stakeholders—they tell us what worries them. Experts listen carefully.
Then the experts go away, do what they’re exceptionally good at, and a gap appears from then on, because those who will be impacted most by the decision were left out of the ideating of solutions. Phrases like “They don’t have the expertise...” and “That’s death by committee...” emerge to explain away the gap.
It’s understandable. While the stakes are high, solutioning is to the expert what art is to an artist, and who wants others in the way of their art?
But the reality is that participation is one of the ways people experience care.
Every point of view can’t make it into the final plan, but the act of engaging with that difference changes what becomes possible. It doesn’t matter how urgent the issue, or how pristine the data behind your solution is, people care about causes when they feel personally recognized inside the process shaping their future.
How to Build What Actually Holds Belief in Place
Here is what I told my councilman in that first conversation:
“The collective action you’re envisioning hinges on relational gravity.”
Relational gravity is the mutual, stabilizing force that makes it possible to act together, even in uncertainty. When it’s not there, logic and persuasion is mostly useless. Outsiders remain outsiders. And the ideas you care about crumble to familiar patterns of tension and ambient friction.
Relational gravity never begins with alignment.
It begins with the signals they can observe from a distance:
How you meet them where they are
What you amplify with them
To do both, stay genuinely curious about their thinking — longer than feels comfortable, longer than feels efficient. It’s as simple as meeting statements like these with responses and questions that allow you to linger with them:
“You’re making a big mess of things.”
→ “Help me understand what you mean...”“The neighborhood is really going to suffer.”
→ “Can you talk to me about what you’re noticing?”“We’re losing what makes this place special...”
→ Take a beat, count to 5 (or long enough) to signal you’re there to hear their story, because they want to share.
Relational gravity is what forms when someone feels their ideas actually had a place to land.
It’s less about what you say and more about how much room you leave.
Remember that there are fine lines with Relational Gravity, between “just giving someone air time” and actually hearing them; between asking to understand, and just plain leading the witness; between just permitting difference and truly valuing it as part of your process. The goal is never condescension in disguise.
Your goal is to linger with their thoughts long enough to truly build with someone instead of at them.
Deepening Your Capacity for Relational Gravity
&Human’s upcoming Connection Design Lab focuses on Relational Gravity.
It’s an experiential lab design where you’ll get hands-on practice understanding how to connect with skeptics, and facilitating through difference, without needing to win them over.
If your work involves bringing people together to create new solutions, we want you there.
Thursday, June 18th @ Noon EDT
