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Your best clients aren't telling you everything. Not because they don't trust you. But because they don't know what they don't know. They assume if something important needed to happen, you'd bring it up. And when you don't, they figure it's either not relevant to them, or it's already handled.
Meanwhile, opportunities slip by. Tax savings go unclaimed. Risks go unaddressed. And your most valuable clients quietly wonder if there's someone out there who could be doing more for them.
The truth is, proactive conversations are what separate transactional advisors from trusted partners. The advisors who thrive aren't necessarily smarter…they're simply willing to start conversations that others avoid.
Here are 5 conversations your best clients secretly wish you'd start, one for each area of a comprehensive Virtual Family Office, along with the exact language to open the door.
1. Tax Planning: "Are You Comfortable with What You're Paying in Taxes?"
What they're thinking: "I feel like I'm paying too much, but my accountant just files what I give them. Is there anything else I could be doing?"
Most high-income clients and business owners assume their accountant is handling tax strategy. In reality, most accountants focus on compliance…accurately reporting what happened last year. Yet they’re not proactively reducing what happens next year.
Your clients may be sitting on six-figure tax savings opportunities and have no idea. They're waiting for someone to bring it up.
How to start the conversation:
"When's the last time someone sat down with you, not to file your taxes, but to actually strategize around reducing them? Most successful people I work with feel like they're paying more than they should, but they've never had anyone show them what's actually possible. Would it be valuable to take a look?"
This opens the door to discussions around cash balance plans, tax credits, cost segregation, opportunity zones, charitable strategies, and dozens of other planning opportunities that go far beyond traditional compliance.
2. Risk Mitigation: "What Happens to Your Family If Something Happens to You?"
What they're thinking: "I probably need to update my insurance, but I don't even know if what I have is right. And honestly, I don't want to think about it."
Risk conversations are uncomfortable, but your clients think about this more than you realize. They just don't know how to bring it up, or they're afraid of being sold something. The result? Outdated coverage, gaps in protection, and families that would be financially devastated by an event that was entirely preventable.
How to start the conversation:
"I know this isn't anyone's favorite topic, but I'd be doing you a disservice if I didn't ask: if something happened to you tomorrow, would your family be okay? Not emotionally, I can't help with that, but financially. Do you know for certain that everything is set up the way it needs to be?"
This creates space to review life insurance adequacy, disability coverage, long-term care planning, key person coverage for business owners, and even advanced strategies like captive insurance for the right clients.
3. Wealth Management: "Is Your Money Actually Working as Hard as You Are?"
What they're thinking: "I've got money in a few different places, but I have no idea if it's optimized. Am I missing something?"
High-net-worth clients often have accumulated assets across multiple accounts, advisors, and platforms over the years. They've got the 401(k) from three jobs ago, a brokerage account they opened a decade ago, some real estate, maybe some alternatives they were talked into at some point.
But nobody is looking at the full picture. Nobody is asking how all of these pieces work together, or whether they're creating unnecessary risk, tax drag, or missed growth opportunities.
How to start the conversation:
"I'm curious, do you feel like all of your investments are working together toward the same goals? Or does it feel like you've got a collection of accounts that just kind of happened over time? Most people I talk to feel like they've never had someone look at the whole picture and make sure everything is actually coordinated."
This opens the door to comprehensive wealth management conversations, asset allocation reviews, alternative investment considerations, retirement income planning, and coordination between liquid and non-liquid assets.
4. Legal Services: "When's the Last Time You Looked at Your Estate Plan?"
What they're thinking: "I set up a trust years ago and haven't touched it since. I hope it still does what I need it to do."
Most clients have some legal documents in a drawer somewhere, a will, maybe a trust, possibly a power of attorney. But life changes. Tax laws change. Family dynamics change. And those documents gather dust while the world moves on.
The clients who think they're "all set" are often the ones with the most outdated plans. And they won't find out until it's too late to fix.
How to start the conversation:
"Quick question, when's the last time you actually reviewed your estate plan? Not just confirmed it exists, but sat down with someone and made sure it still reflects your wishes, your family situation, and the current tax laws? I ask because I've seen a lot of people assume they're covered, only to find out their plan was built for a completely different life."
This opens the door to discussions about trust updates, asset protection strategies, beneficiary reviews, entity structuring for business owners, buy-sell agreements, and ensuring legal documents align with the overall financial plan.
5. Business Advisory: "What's Your Plan for the Business—Long Term?"
What they're thinking: "I've poured everything into this company, but I don't really have a plan for what happens next. I don't even know who to talk to about it."
Business owners live inside their businesses. They know every detail about operations, clients, and cash flow. But when it comes to the big picture like exit strategy, succession planning, business valuation, growth optimization, they often feel completely alone.
They don't need another person trying to sell them something. They need someone who will sit down and ask real questions about the future of their life's work.
How to start the conversation:
"I know the business is your baby…you've built something real. But I'm curious: have you thought about what the next chapter looks like? Whether that's five years from now or fifteen, do you have a clear picture of how you want things to unfold? Most business owners I work with have put so much energy into building that they haven't had time to think about what comes next."
This creates an entry point for conversations about succession planning, exit strategy development, business valuation, key performance indicators, leadership development, and all the ways an advisor can help a business owner protect and maximize their greatest asset.
The Common Thread: Proactive Over Reactive
Notice what these 5 conversations have in common: none of them are about selling anything. They're about asking better questions. They're about demonstrating that you're thinking about your clients' full financial picture, not just the slice you happen to manage.
Your best clients want to be served comprehensively. They want someone who looks ahead, identifies opportunities, and brings solutions before problems become emergencies. They want a trusted partner, not a product pusher.
When you start having these conversations, something shifts. You stop competing on rate of return or product features. You start competing on the depth of the relationship, and that's a competition most advisors can't even enter.
So here's the challenge: pick one of these conversations and have it with your next client meeting. Not to sell anything…just to open a door. You might be surprised what walks through.
