Asking, Not Telling: A Lesson from Las Vegas

May 2025

Recently, I caught myself complaining to my husband that my teenage son wouldn't listen to my very helpful advice on preparing for the SATs. My husband gently suggested I try asking more pointed questions, ones that might prompt our son to reflect on what he wants to do to reach his goals, rather than offering my usual monologue about what I think he should do.

Of course. I'm a trained mediator. I know that insight and change come not from lecturing but from asking the right questions. Yet somehow, when it came to parenting, I forgot that lesson. My son’s glazed-over eyes during my monologue were proof that advice alone rarely moves people. But the right question? That can shift everything.

In mediation, I see this play out all the time. In a recent session, one party described herself as thrifty with her money. We chatted briefly about how we each enjoy spending money – whether on shows or gambling in Las Vegas. She shared that she disliked the uncertainty of gambling; she wanted to know exactly where her money was going. Later, I gently asked: Would you feel more comfortable with the certainty of accepting the current offer or with the gamble of litigation?

She didn’t answer directly. But not long after, the matter settled. I don’t know whether she’ll ever set foot in Las Vegas. But in that moment, she weighed her options like a careful player at the table, not just with her wallet, but with her values and comfort with risk. And that's the magic of a good question: it invites people to pause and consider for themselves whether to double down or walk away.

So what makes a question "good"?

Curiosity. A good question doesn't push someone toward the answer I want; it draws them toward the answer they need.

In mediation, I often find that the most powerful questions are the simplest ones, like:

• What would a good outcome look like for you?

• What are you most worried about if this doesn't settle?

• What would make this feel fair to you?

These kinds of questions invite people to think more deeply about their goals, their values, and what they can live with. They create space for reflection, not resistance.

The same principle applies outside the mediation room. When I asked my son, What do you think your SAT study plan should be to feel confident on testing day?, instead of rattling off what I thought he should be doing, our conversation was more fruitful and my son was more engaged.

Asking thoughtful questions isn’t just about gathering facts.

It’s how we connect with people, uncover motivations, and help them imagine different outcomes. The best questions come from a place of genuine curiosity and compassion, and when done right, they can lead people to their own best decisions.

Because whether you're guiding a party through conflict or helping a teenager navigate the SATs, the right question is often more powerful than the perfect advice.

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