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Three questions that can change any difficult conversation

spencermatthews1
22 hours ago
3 min read

You don't need to win the argument. You need to understand it.


When a disagreement gets heated, most of us instinctively want to argue back, correct the record, or prove our point. It's a very human response. But here's the thing: in almost every conflict, both sides are convinced they're right. And they're usually not arguing about facts alone. They're arguing about meaning - whose version of events is real, whose sense of fairness counts, and who gets to make the call.


Over many years working in mediation and dispute resolution, one approach keeps proving its worth: asking simple, curious questions rather than making confident counter-claims. And three questions in particular do a remarkable amount of heavy lifting.


Not aggressive questions. Not clever gotcha questions. Just genuinely curious ones.


QUESTION ONE

"How do you know that?"

This question gently asks someone to trace their certainty back to its source. Not to challenge them, but to understand them — and to help them understand themselves.


When someone says "they never listen to us" or "this process is completely unfair," they've usually moved from an experience to a conclusion without stopping to examine the steps in between. Asking "how do you know that?" creates that pause. It invites them to notice the difference between what they observed and what they decided it meant.


Asked with real curiosity, this question rarely puts people on the defensive. More often, it slows things down in a useful way. People begin to hear themselves more clearly - and sometimes, that's when the conversation genuinely shifts.


QUESTION TWO

"Compared to what?"

Every claim about fairness involves a hidden comparison. This question brings it into the open.


When someone says an offer is insulting or an outcome is unacceptable, they have a benchmark in mind - often an unstated one. "Compared to what?" brings it into the open. What were they expecting? What would feel fair? What similar situation are they measuring against?


Sometimes that benchmark turns out to be entirely reasonable. Sometimes it's based on a misunderstanding, or a comparison that doesn't quite apply. Either way, naming it out loud gives everyone something real to work with. Positions that felt fixed often become surprisingly flexible once the underlying standard is visible and can be discussed.


QUESTION THREE

"Who decides?"

Beneath most conflicts is a quieter disagreement: who has the authority to settle this?


This question cuts to the heart of many disputes that appear to be about facts or fairness, but are really about legitimacy and control. Do the parties themselves have the power to resolve this together? Is there a formal process? An agreed-upon decision-maker? And if no agreement is reached, who has the final say anyway?


Making that structure explicit helps people understand what's actually within their reach. It also tends to make the conversation more realistic - which, in difficult disputes, is often exactly what's needed.


These three questions aren't a rigid formula. They're more like a mindset: approach what you don't yet understand with curiosity before you respond with certainty. In practice, one question often leads naturally to another. Exploring a fairness claim through "compared to what?" might reveal an assumption that invites "how do you know that?" - and that in turn might surface a question about who actually has the authority to decide.


What makes them work isn't cleverness. It's tone. Asked with genuine interest, rather than as a challenge, these questions create breathing room in conversations that have become rigid. They don't resolve conflict on their own, but they make resolution possible, which is often more than enough.


If you're navigating a difficult conversation at work or in your community and want to think it through, I'd love to hear from you. Visit smadvisory.net to learn more about how I work.




 
 
 

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