Tuesday Email: The Empathy Gap

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

You're nodding.

Making eye contact.

You're present in the meeting.

But here's what's actually happening in your head: you stopped listening about thirty seconds ago.

Your client is still talking, but you're not tracking their words anymore.

You're building your response.

Crafting your next question.

Replaying what they said two minutes ago and forming an argument about why their concern about market volatility is overblown.

There's a term for this: cognitive lag time. The several seconds to a minute between hearing words and grasping what someone actually means. And during that lag, we stop listening to the speaker and start listening to ourselves.

We've all done the thing where we're in conversation, someone's talking, and suddenly we realize we've been daydreaming.

We snap back. Oh shoot, what did you say?

But we don't want to admit it, so we just keep going. Or worse—we laugh at the exact moment they tell us something sad because we weren't actually listening.

This is a human problem. Which makes it an advisors problem who is in the business of serving humans.

And the problem is getting more exposed by the minute.

Your AI is transcribing every word. You have perfect notes. You'll never miss a detail again.

And you're still missing everything that matters.

Here's what's happening across our industry right now: we're getting increasingly sophisticated AI integrated into our firms. Meeting transcripts. Automated summaries. Perfect records of every client conversation. And we think this solves the listening problem.

It doesn't. It reveals it.

Because having the content doesn't mean you have the context.

I'm watching this play out in real time at the firms I talk with.

We have full transcripts of client meetings. Every word captured, searchable, retrievable.

But the distinction between hearing words and understanding meaning? That's becoming the actual differentiator of value.

Everybody has the full content of every conversation now. Where we're going to separate ourselves is in distilling that content by understanding the context. By deeply engaging in the conversation itself.

Look, this isn't actually different than how it's always been. The differentiator in wealth management has always been: can you build trust? Can you establish a relationship? Can you create belief in what you're selling?

What's different is that we can't hide behind note-taking anymore.

The opportunity—if we're willing to take it—is leveraging technology not to ease back in a conversation or take a break, but to lean into conversations with more presence.

AI handles the notes. Which means you should be more present in your meetings. More empathetic. More able to navigate and meander through a conversation without worrying about capturing everything.

And here's the thing about meandering: it's not a bad thing in conversation. Meandering is your ability to have true curiosity. To follow the thread of feelings and examples and questions wherever they lead. That's where you create the deepest connections.

But it requires understanding a critical distinction.

I grew up with a sewer grate right outside our house.

You could pop it open, climb down the ladder, and you'd be in the actual sewer system. We did this all the time as kids.

Stay with me here.

Sympathy is standing at the top of that open grate. Someone's down in the hole, unable to get up the ladder, and you yell down: "Hey, I'm so sorry you're down there. Here's a sandwich." You're solving the problem you think they have.

Sympathy is about providing sandwiches as the perceived solution.

Empathy, on the other hand, climbs down the ladder into the hole with the client. It sits in the muck with them to acknowledge they're not alone in their suffering. Not to fix it. To understand it.

In practice, this looks like:

Sympathy: "I understand that the portfolio is down, but at least the market isn't as bad as 2008."

Empathy: "Tell me more about how that makes you feel. Where do you think that fear is coming from?"

One minimizes. One validates.

One creates distance. One creates connection.

And here's what makes this hard: we're trained as problem solvers.

That's what we grow up learning in this industry. Someone presents a situation, we pattern-match it to something we've seen before, we deliver the solution.

Clients even expect this. They come to us wanting answers.

But the reality is that problems—actual financial planning problems—can increasingly be solved technologically. The math, the optimization, the scenario modeling. AI can do that.

What AI can't do is climb down into the hole.

The question is: why did the last financial advisor not work? Why have you struggled to save more? What happens inside you when you think about spending money in retirement?

These aren't therapy questions. These are the questions that help you build a financial plan they'll actually follow.

Because research shows that advisors who deliver a financial plan before listening to the client's historical relationship with money are significantly more likely to encounter resistance or non-compliance.

Clients suggest their true concerns through clues. Expressions of feelings. Personal stories. Unusual silences. You need what researchers call a "diagnostic ear" to catch them.

But you can't catch clues if you're listening to respond.

We all do this.

Someone says something we disagree with, and while they're still talking, we start building our counter-argument in our heads. Or we think, "Better to ask questions," so we start formulating the perfect question while they're mid-sentence.

That's listening to respond.

It's characterized by preoccupation with preparing your next move. By offering solutions before the client finishes speaking. By assuming you know where this is going because you've seen it before.

Miller's Law says we should assume what someone says is true and try to imagine what it could be true of. Most of us run Miller's Law in reverse: we assume the speaker is wrong and look for evidence to support that judgment.

And look, I get the objection. You're thinking: But I have experience with this. I've seen this situation twenty times. Shouldn't I just get to the solution? That's what they're paying me for.

Maybe.

But there's a reason they're sitting across from you and not the last advisor who also had the solution.

You've got to understand how to present that solution in a way that actually lands. Which means understanding their context, not just hearing their content.

There's research on something called empathic accuracy—the extent to which you can accurately infer the specific content of another person's thoughts or feelings.

It requires two distinct neurological processes:

Affect sharing: Experiencing a similar emotional state as the other person.

Mentalizing: Cognitively labeling that state.

Here's what that means in practice: They're upset. You've got to connect to something you experienced in your life. It doesn't have to be the same exact thing, but it's got to draw a similar feeling.

They're anxious about retirement spending? You remember a time you felt anxious about money. What did that feel like in your body? What were you worried about? What stories were you telling yourself?

You put yourself in that state. You label it: This is fear. This is uncertainty. This is loss of control.

And now you can have a different conversation. Because you're not theoretically understanding their concern—you're resonating with it.

This is what an algorithm can't replicate. When an advisor demonstrates high empathic accuracy, they're witnessing the client's internal world with authentic resonance.

But you can't do this while simultaneously planning your response.

So here's what I'm asking you to try: When you think you've heard what you need to hear, when you have the answer, ask one more question.

And make it thoughtful. Don't prepare it while they're talking. Listen. They finish. Pause for five or six seconds. Think. Then ask.

Try this: "It sounds like you're feeling overwhelmed by all of this. Tell me more."

That's Carl Rogers' technique of reflective listening—paraphrasing the feeling behind the words, not just the content. And then inviting them to go deeper.

It creates comfort. Psychological safety. Permission to share what they're actually worried about.

My son lost his second tooth.

The first one had gone fine with the tooth fairy, but this time he was more aware. More nervous.

He was terrified of the tooth fairy flying through the window and coming into his room. The idea of something entering his space while he slept was genuinely scary to him.

I knew this.

And as I went to do the “tooth fairy’s” business, he woke up in mid action of exchange of tooth for money (sorry if you still thought the tooth fair was real!).

It was chaos for a second, but quick thinking and the ability to throw the tooth outside the room via a jack and jill bathroom door saved me.

Although I navigated through the incident, it didn’t help his nervousness.

He wasn’t able to sleep. Every time he tried, he’d be down in our room 15 minutes later.

And it was late, he kept coming downstairs, and I was exhausted.

After the fourth or fifth trip down, I lost it. I went upstairs and basically said we're never letting the tooth fairy come again, and stormed back to bed.

Lying there, I felt terrible. And then I had this thought:

How is he supposed to know?

He'd never experienced this before. The concept of something flying through a window into his room was objectively frightening. I understood the tooth fairy tradition because I'd lived it. I had the context.

But I got mad at him for not having understanding I'd gained through decades of experience.

I had the content—his fear, his resistance to going to sleep. But I gave zero credit to the context. He'd never done this before. And because I didn't go deeper, because I didn't ask questions, I just reacted based on the content alone.

This is exactly what we do with clients.

We hear their situation. We see the content. And we assume they have the context we have. That they understand what we understand. That they see it through the lens we see it through.

But I'm the only one who's ever lived my life. And even though I may have an answer, I may not have their answer. Because they're living their life through their own lens.

The only way I can get there is by asking questions. Going deeper. Connecting what they're telling me to something I've felt so I can create resonance.

Until I do that work, I've got content. But I'm missing the context that actually matters.

The reality is this: AI is giving us perfect transcripts. Perfect notes. Perfect content.

Which means context—the meaning behind the words—is the only battlefield left.

You can't outsource empathy. You can't automate climbing down into the hole with someone.

But you can use technology to free yourself up to do that work.

Ask one more question. Pause before responding. Connect to what you've felt.

That's the gap. And it's the only one worth closing.

The best is ahead!

-Matt