Sometimes the question your client asks isn’t the one they actually need answered.
The other day, my daughter texted me what I thought was a simple question about retirement planning.
As a tax professional, I did what came naturally: I launched into an explanation. I answered the technical question she asked, explained how Roth IRAs work and felt pretty confident I’d covered it.
She replied with one emoji.
🫠
It’s the one that looks like a melting smiley face.
If you know, you know. And I did not. She said it basically translates to, “My brain has melted.”
It made me laugh, but it also made me stop and think.
I’d answered her question accurately, but I hadn’t answered the question she was really asking.
As accountants, we’re trained to explain how things work. We know the legislation, the thresholds, the rules, and the tax implications. So, when someone asks us a technical question, our instinct is usually to explain the mechanics. But our clients aren’t approaching those conversations the way we are.
To us, retirement planning is a financial product. To them, it’s wrapped up in questions like, Am I already too far behind? Am I doing enough? What if I get this wrong? Will I ever actually be able to require?
Those aren’t technical questions. They’re emotional ones.
And if we answer an emotional question with a technical explanation, we shouldn’t be surprised when the response is a melting smiley face emoji.
Instead of leading with “Here’s how pensions work,” try leading with “You’re not behind just because you’re thinking about this now.”
Instead of listing contribution allowances, start by reassuring them that retirement planning isn’t about making one perfect decision today. It’s about taking the next sensible step.
Instead of explaining every investment option available, ask them what they’re hoping retirement actually looks like. Do they want to stop working completely? Reduce their hours? Travel? Spend more time with family? That conversation tells you far more than jumping straight into the mechanics ever will.
Of course, the technical advice still matters. But people are much more likely to absorb it once you’ve addressed the worry sitting underneath their question.
If we jump straight into explaining the rules, we’ve skipped the most important part of the conversation.




Not hearing the emotional question is pretty common among financial advisors, especially as clients approach retirement! Addressing the emotional issues, as well as de-mystifying Wall Street is a focal point for my practice after spending 40 years working on the Street!