Years ago, I was coaching a young salesperson who kept getting derailed during presentations. A prospect would ask about some minor feature—something that didn’t matter, something that pulled the conversation away from the real value—and he’d dutifully answer it. Then another question. Then another. Before long, he’d lost control of the room.
I told him something I’ve told every mentee I’ve ever had: “Answer the question you want to answer, not the question you were asked.”
He looked at me like I’d just suggested lying.
“I’m not telling you to be dishonest,” I said. “I’m telling you to redirect. When someone asks you about a feature that doesn’t matter, acknowledge it—then pivot to what does matter. Control the direction of the conversation. Don’t let them steer you into the weeds.”
He practiced it. He got good at it. And it changed how he sold.
I didn’t know it then, but decades later, that same principle would become one of the most important tools in my caregiving toolkit.
Gail asks me the same question multiple times a day now. Sometimes it’s “Where’s my mother?” Sometimes it’s “When are we going home?” Sometimes it’s something I can’t even track anymore because the question itself doesn’t make sense outside her world.
Early on, I tried to answer honestly. I tried to correct her, gently, with facts. “Your mother passed away, sweetheart. A long time ago.” But facts don’t comfort someone with dementia. Facts just reset the grief. She’d hear the news like it was the first time, and I’d watch her heart break all over again.
So I stopped answering the question she asked.
Now, when she asks about her mother, I answer the question I want to answer. I say, “Your mom loved you so much. Tell me about her.” And just like that, we’re not talking about death. We’re talking about memory. We’re talking about love. She’ll tell me a story—sometimes one I’ve heard a hundred times, sometimes one I’ve never heard before—and the loop is broken. Not because I corrected her, but because I redirected her.
When she asks when we’re going home, I don’t say, “We are home.” I say, “We will. But right now, let’s sit here by the fire for a bit. The river looks beautiful today.” And she settles. Because the question wasn’t really about geography. It was about feeling safe. Feeling oriented. Feeling like she belongs somewhere.
Answer the question you want to answer.
This isn’t manipulation. It’s compassion. It’s recognizing that the question being asked isn’t always the question that needs answering. Sometimes the real question underneath is: “Do you see me? Am I safe? Do I still matter?”
And those questions—those I can answer. Every single time.
The young salesperson I coached all those years ago learned to redirect a conversation to close a deal. I didn’t know I was teaching him the same skill that would one day help me navigate the most difficult conversations of my life.
But maybe that’s the thing about good advice. It works everywhere. In boardrooms and bedrooms. In sales presentations and dementia loops. In moments when someone asks you a question you can’t answer truthfully without causing pain.
You acknowledge what they’re asking. You meet them where they are. And then you gently, kindly, redirect them to the answer that actually helps.
Answer the question you want to answer, not the question you were asked.
In sales, it keeps you in control of the conversation.
In caregiving, it keeps you both in a place of peace.
And sometimes, that’s the most important deal you’ll ever close.
– Gregg
