Articles
The Gift of a Good Question
12.03.2025
If we have been blessed to serve as your trusted advisor for any length of time, you know that at Rather & Kittrell we like to ask a lot of questions. We’ll ask about what’s most important to you when it comes to your money, what your goals are—both big and small—who matters most in your life, and what fears or concerns keep you up at night. For us, truly knowing you is essential if we’re going to offer guidance on plans that impact not just you, but also those you care about most.
But our questions aren’t limited to our clients. On a regular basis, we hear about and evaluate various investment strategies, insurance options, and financial products. It’s our duty to ask good questions as we consider whether these tools might benefit our clients. If we don’t ask thoughtful questions, we can’t know whether something is truly in your best interest.
Recently, there was an article about Kyle Busch and an insurance investment that went wrong for his family. Without going into the details, I can say that many important questions were left unasked. The investment might have been appropriate if all the right questions had been asked and fully understood by everyone involved—but unfortunately, that doesn’t always happen.
When I read that story, it reminded me of one of the sharpest minds and best question-askers I’ve ever known, Chad Starliper. Chad was a wonderful advisor, friend, and mentor who passed away eight years ago. I remember one meeting where he asked such a detailed question about an investment product that even the provider pitching it to our firm was stunned. But his question—and the answer it prompted—completely changed how we evaluated that investment for our clients.
As fiduciaries, it’s our responsibility to ask questions the way Chad did. He never asked to challenge or offend; he asked to understand. He wanted to grasp every detail—the pros and cons, and the potential impact on the lives of our clients.
In the financial world, a fiduciary is someone who puts the clients’ best interests ahead of their own. A fiduciary acts in the best interest of their clients. A fiduciary acts with prudence and diligence when determining if a recommendation is right for the client, even if it means lower financial benefit to the advisor.
Sitting across the desk from Chad and watching him think through those implications and ask his questions was one of the greatest gifts he ever gave me, even though he likely never realized it.
Asking good questions is built into the DNA of Rather & Kittrell. From the day I arrived in our offices 13½ years ago to today, we’ve continued that tradition—asking questions of prospective clients, current clients, each other, and those introducing us to new ideas. Sometimes the best gifts come as big surprises, but often even those surprises begin with someone taking the time to ask a thoughtful question—one that helps reveal what truly brings a smile.
Amanda Howerton, CFP® is a Senior Advisor with Rather & Kittrell.

