Ask an Advisor: What did your worst client meeting teach you?

Published August 7, 2026 6:06 PM

Updated August 7, 2026 6:09 PM

1 Min Read

Tense, difficult moments are a natural part of human interaction. For financial advisors, whether seasoned pros or new recruits, it's a given that even the most successful have experienced a "bad" client meeting. After all, achieving a 100% satisfaction rate with customers is unrealistic, given the inherently emotional nature of the business.

When a meeting goes sideways, no matter how much prep work or training an advisor has under their belt, it can be easy to dwell on what went wrong. But difficult client interactions can also offer valuable takeaways for advisors.

Rather than staying rattled after a difficult meeting, one way to make the most of such moments is to recognize that they are part of the job — and that savvy advisors can take the lessons from challenging encounters and turn them into teachable moments with lasting, tangible takeaways. Done well, working through such rough patches can even deepen trust and strengthen the client relationship.

In this installment of Ask an Advisor, we posed the question: What did your worst client meeting teach you?

Here is what they had to say:

Recognizing the client’s unspoken cues

Shane Tenny, managing partner at Spaugh Dameron Tenny in Charlotte, North Carolina

My worst client meeting was with a retired couple in their 60s. She was very engaged, but he was extremely grumpy, giving short answers and kept staring off totally unengaged.

After about 30 minutes, I was trying to determine whether to just keep pretending the conversation was normal, but with the echo of some recent coaching in my ear, I decided to just speak what I was feeling. I simply paused and said, "I think we should pause for a moment. I'm feeling very uncomfortable because it seems like you would rather not be here right now. I'm not sure if you're not feeling well or I've said something offensive, but I'm happy to reschedule to end if another time would be better."

He immediately sat up straight, apologized, said that it'd been a tough day at work, and asked if we could take a break for him to use the restroom. The rest of the meeting went so much better!

The value of setting clear expectations

Jon Lapp, advisor and founder at Haven Financial Advisors in Lancaster, Pennsylvania

My worst client meeting was when I was fresh out of college and starting in the insurance broker-dealer space. Our training was to call anyone and everyone, with the sole intent of booking a meeting.

I guess some of the script was a little too vague, because I had someone show up to a meeting thinking they were coming for a job interview! They were cool about it and also felt embarrassed, so it ended up being funnier than anything. But it taught me a good lesson about upfront clarity, and I'm very grateful I'm past that stage of my career.

Empathy leads the way

Davi Kutner, partner and advisor at Aprio Wealth Management headquartered in Atlanta

Topics discussed in a client meeting can potentially trigger responses or reactions that are outsized. Over time, I have learned that talking about people's life savings can be highly emotional. Our lives are highly complicated and multifaceted, and we all have a lot going on. We never know everything someone is dealing with at any given point in time, and those circumstances can influence responses and reactions.

I have learned over time to be more empathetic and understanding, which can go a long way toward de-escalating tense moments. Additionally, when trust and confidence is built up over time, it is much easier to overcome tough or difficult circumstances. Everyone has a bad day sometimes, and that's OK.

One of the aspects of wealth management that I enjoy most and that provides me with the most fulfillment is developing meaningful long-term relationships with my clients, which has proven beneficial over time during difficult client meetings.

You can’t win ‘em all

Andrew Rosen, executive chairman at Diversified in Wilmington, Delaware

You can't help people that aren't ready to listen. This was a lesson I learned early on, when I wanted to help everyone I could. I realized that I met with certain people I knew I could help, and yet, as much as I wanted to spend my time convincing them, I realized there are so many people out there who actually want my help, which is a better use of resources.