Tuesday Email: The Questions You're Not Asking

Happy Tuesday!

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

The core of what we do, things like investment management, financial planning, etc. is actually not the center of the questions we should be asking our clients.

I know that sounds backwards.

We build our expertise around technical fundamentals; financial planning, portfolio allocation, security analysis. But these core competencies aren't where the deepest relational value lives.

And the thing is, we know that, but continually fall back towards it.

Those relationships that are sticky, our best referrers, our longest tenured clients… those relationships live in what we perceive as being uncomfortable.

These relationships are built with us living outside the core of what we do. They are built on living on the periphery of what we traditionally think of as our job. And that creates a real dilemma, because we feel competent and confident asking about asset allocation and retirement timelines. We feel significantly less confident asking about what scares our clients at 3am or what their biggest regret is about raising their kids.

That uncomfortable ultimately becomes comfortable, the more we do it and the longer we work with clients.

But if you stay on just the comfortable with the core questions, the investment management ones, we create something I've been thinking of as a commodity-driven relationship.

What is a commodity driven relationship?

It's a relationship where your service offering is stuck on the commodity you're delivering, for us that is quickly becoming investment management. And investment management is driven by things outside our control like the markets, the ups and downs, the fluctuations.

When our value proposition reverts to the mean (and it will), that commodity-driven relationship becomes volatile.

We all have these relationships. But we also have the other kind.

Do this exercise with me: bucket your clients into three groups. First, the factual clients those that you serve well, they ask good questions, but they're transactional. You don't know much about them beyond the spreadsheet. Second, the friend-like clients those relationships where there's warmth, some personal connection. Third, the deep relationship clients which are the ones where you rarely spend much time talking about the numbers because the conversation goes somewhere else.

Those last two buckets? Those are the ones that feel the most impactful. Those are the meetings where we leave feeling like we actually made a difference. The factual clients, well they're fine. We do good work for them. But they don't give us that sense of doing something deeper.

So here's the uncomfortable question: what if all our conversations were like that? Like those in the second two buckets?

And I already know the objection forming: "But Matt, the factual people don't want that. They'd leave if I started asking deeper questions."

And my response is: is that a bad thing? Or does that give us more capacity for the people who want what we actually have to give?

As the world continues to evolve at an accelerating pace, we begin to see the need and the opportunity. The commodity that is forming which is investment management and financial planning mechanics can be automated. AI can run Monte Carlos. Algorithms can rebalance portfolios. The non-commodity aspect which are the relationship, that connection, that depth, those cannot be replicated by technology.

So do we want to be in this business of doing the commodity or do we want to be in the business of doing the non-commodity?

The industry is moving toward an answer whether we're ready or not.

I like to nerd out a bit about the brain.

And it’s super interesting to see what happens in our client’s brain when we ask a simple question.

We're in a review meeting and we ask: "Did you maximize your 401k contributions this year?"

Seems straightforward, right? Non-intimidating. A factual question we need answered to do our job properly.

But here's what actually happens: the brain frequently perceives that inquiry as a test of competence or a judgment. Our client knows immediately whether they did or didn't max it out. They think they know the "right" answer. And in that moment, their amygdala, the area of the brain that processes our emotions, triggers a mild threat response. Their cognitive focus narrows. They get defensive, brief, or evasive. They shut down.

All we did was ask a simple question. Yet, it was transactional and we have now closed the door to deeper conversation.

Now contrast that with this: "Tell me about your 401k."

That open-ended, exploratory question activates the prefrontal cortex, the area our brain that spurs creativity, collaboration, problem solving and imagination. The juices start flowing when this part of the brain activates. We’ve shifted the client from a defensive, reactive posture into something forward-looking.

But here's the core thesis, and this is from the research that made me rethink everything: "The efficacy of a question is not determined merely by the objective information it extracts from a client, but by the cognitive, emotional, and psychological processes it initiates within the respondent."

Read that again.

Questions that spur a feeling, a thought, a rethinking of the world, that is the power of the question, not the response they provide.

When we ask a great question, we're not gathering data.

We're creating an experience.

We're making them think.

We're helping them view things differently without telling them how to view things. A question lets their mind come to conclusions themselves, which gives them ownership of that insight.

That's why questions always beat statements. Me telling you something, that will fall on deaf ears. Me asking you a really good question that gets you to the answer yourself? That sticks.

I had this realization while researching this piece, and I can't shake it.

What if every client conversation we have, we approach it as if we're authoring their biography?

I know how that sounds.

It sounds ridiculous, I get it.

But go with me here. If we have a client for 20 years, we should be able to write a biography on them. We should have enough interactions with them where we understand them well enough. We can share where'd they come from, tell others about their parents, their kids, their professional life, raising their kids, the struggles, the ups and downs.

If we've met with someone for two decades across multiple market cycles and countless life events—marriages, divorces, health scares, career changes, losses, celebrations—the amount of life they've lived that we should be asking about and understanding is enormous.

But here's what the research shows: trust is methodically built through what Dr. Arthur Aaron calls "structural escalation of vulnerability."

We can't rush this. We build trust through conversational pacing. We allow clients to gradually open up. We reduce the likelihood that sharing feels one-sided or like an interrogation.

This doesn't mean we need to have one massive deep conversation in the first meeting.

It could be ten minutes within a sixty-minute conversation where we're asking these questions. But even in the other fifty minutes, we're asking thoughtful questions. Maybe they're more focused on helping them think differently about their transactional question, but we're present and curious.

What makes this work is active empathic listening and reflective inquiry. We're genuinely curious.

We're listening, truly listening, not thinking about what we need to say next. And then we're reflecting back: "I heard you say this. That's really interesting. Tell me more about that."

We're pretending that when it's all said and done, we're going to write their life biography.

And if we look at a conversation through that lens, everything changes.

Start here tomorrow: ask a follow-up question.

The simplest, most powerful tool in our arsenal is "tell me more." When a client shares something, don't move to the next agenda item. Pause. Ask them to go deeper. That follow-up question proves we're actively processing their narrative. It shows we're listening without judgment.

And here's something critical from the research: powerful questions are almost never focused on the past. They don't ask clients to justify previous behaviors. It's not "what did you do?" It's "where do we want to go?" Because when we ask about the past, we're analyzing their behaviors. We're judging. And remember what happens when someone feels judged? The amygdala fires. They shut down.

Let me give you a practical tool I've been experimenting with: the bridge.

A client asks a transactional question. Something like: "What do you think the Federal Reserve will do with interest rates next quarter?"

We could answer with a ten-minute macroeconomic lecture. We could dig deep into dot plots and inflation data. And that would be fine. We'd answer their question. But we'd also entrench the relationship deeper into the transaction.

The reality is, they don't really care about the nuts and bolts of Fed policy. The reason they're asking is because they're scared or nervous or worried.

So use a bridge.

"That's a really critical question, and we monitor Fed policy very closely. But what's most important to remember is how that impacts your specific timeline. So tell me, if rates continue to fluctuate, what's your biggest concern regarding your transition to retirement in the next three years?"

We've validated their intellectual curiosity.

We've acknowledged the question.

But we've immediately tethered the abstract macroeconomic concept to their highly personal, emotional purpose. That's an advisor who's highly in tune with their clients.

Here's another framework: FORD. Family, Occupation, Recreation, Dreams.

We can ask surface-level questions in each of these areas, or we can go deep.

Surface level: "What are your kids' names?" Deeper: "What was the greatest thing about raising kids? What was the biggest struggle you faced?"

Surface level: "What do you like to do for fun?" Deeper: "In twenty years, if you had all the money you needed and all the time in the world, what would a day in your life look like?"

Those deeper questions create a neuropsychological reaction. They activate curiosity, creativity, collaboration.

Look, I know some of us are thinking this feels therapy-like or touchy-feely.

And there's definitely a line.

We have to be ready for the answers.

But if we're feeling resistance to this, I'd suggest that maybe we haven't audited our own communication patterns.

It's not always on the other person. It's usually on us.

I learned this lesson the hard way through a relationship with a mentor.

He's older than me, someone who's been guiding me since I was building my technology company.

I always felt like it was one-sided. He was doing me a favor by taking the time. I'd come with questions, he'd have the answers, and I was grateful for it. But it felt transactional—one person with knowledge, one person seeking it.

Then my dad passed away.

A few weeks after it happened, I met with my mentor. He asked me questions. I was vulnerable with him in a way I hadn't been before. I opened up. He listened with genuine interest. And it created this connection, this building block. But still, our relationship felt like it had always felt.

About a year later, something happened to him and his family. And he came to me. He opened up. He was vulnerable. We bonded over something deeper—a conversation where we were both showing up fully, both being human with each other.

And it was after that second conversation that everything shifted. It went from feeling like a one-person-with-knowledge dynamic to a genuine relationship.

Here's what I realized: me being vulnerable was the gift to allow him to know that he could be vulnerable with me.

And it wasn't the next day, or the next week, or the next month. I didn't rush it. When we rush vulnerability, relationships get uncomfortable and awkward. I gave it space and time. And it led to something deeper.

What I learned is that being vulnerable with others gives them the ability and comfort to be vulnerable with you. But there's time in that. There's patience required.

And that lesson applies to every client relationship we have.

We have to be open to opening up ourselves.

We have to be willing to ask questions beyond "how's the weather?" and "when do you want to retire?"

We can't just be the perfect professional who has all the answers. We have to share our challenges, acknowledge we don't have all the answers, show that we struggle too.

When we do that, when we lead by example with vulnerability, we give our clients permission to do the same. Maybe not in that moment. Maybe not in the next meeting. Maybe not for months. But eventually, they become more comfortable. And when you stay consistent with that, you create a deeper, more meaningful relationship.

That is the relationship I personally want to create.

And I think that's the relationship the FutureProof Advisors are constantly working to create, day in and day out, with every single client.

The best is ahead!

-Matt