Are You Asking Enough Questions – Or the Right Ones?

There’s a commercial out now where a young boy asks his father about a meeting with his “wealth advisor.” The tagline asks, “Are you asking enough questions?” — a clever and compelling prompt. But I’d argue the more powerful version would be: “Are you asking the right questions?”

It’s easy to ask a lot of questions, but if none of them get to the core of an issue, you’re not likely to land on the answer that really matters. That leads us to an even bigger question: How do you know what the right question is? That’s not always intuitive — in fact, it often takes help from someone with deeper insight to guide you there. At Gainplan, we believe part of our value is helping clients uncover and ask the right financial questions, but this concept applies far beyond money.

A Lesson on the Golf Course

Just last week, I experienced this exact principle in an unexpected place: the golf course. I was paired with an 80-something-year-old man who had played in numerous Michigan Amateur tournaments and had even been inducted into the Michigan Golf Hall of Fame. Every shot he hit was effortless and square on the clubface. I had been trying to find some rhythm in my swing all day, and on the 17th hole, he asked if he could offer me a suggestion. I had been waiting since hole one.

He started by asking what I thought I was doing wrong. “I’m standing up and coming out of the shot,” I replied. He agreed. Then he asked something I hadn’t considered: “Do you think you’re standing up down-to-up or right-to-left?” Without thinking too much, I answered, “Down to up.” He looked at me and said, “No — you’re standing up on your back leg and never getting to your front foot.”

That small correction changed everything. My next two shots were some of the cleanest I’ve ever hit. His secret? He asked a better question than I ever would have thought to ask myself — and that better question led to the right solution.

Financial Questions Are No Different

That golf tip reminded me of the role a great financial advisor plays: someone who doesn’t just answer your questions but helps you refine them until you’re asking the ones that really matter.

You may not be getting the right answers — not because you’re failing to ask questions, but because you’re asking the wrong ones. A good advisor listens closely, observes carefully, and then offers questions that shift your thinking, clarify your priorities, and bring you closer to your goals.

At Gainplan, we’re not here to overwhelm you with information — we’re here to guide your thinking, identify blind spots, and most importantly, help you ask the right questions. Because only then can you truly get the right answers — and the peace of mind that comes with them.

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