7 Tax Conversations Your Advising Clients Are Waiting for You to Start

92% of high-net-worth individuals say they want tax planning. But only 25% feel like they're actually receiving it. That gap isn't because clients don't care. It's because they're waiting. Waiting for someone to bring it up. Waiting for their accountant to mention it. Waiting for their advisor to start the conversation.

Most accountants are focused on compliance. They're filing returns, not proactively recommending strategies. And most advisors assume taxes are "someone else's job." Meanwhile, clients are paying tens of thousands, sometimes hundreds of thousands, more than they need to, every single year.

The opportunity isn't just about saving clients money (though that's huge). It's about positioning yourself as the advisor who actually addresses the things that keep them up at night. Tax frustration is universal. Being the one who solves it is how you become indispensable.

Here are 7 tax conversations you can have with clients right now and the exact language to open the door.

1. The "Am I Overpaying?" Conversation

What to look for: Any client with W-2 income over $250K, significant business income, or a combination that puts them in a high tax bracket. Bonus points if they've complained about their tax bill or mentioned feeling like they "pay more than they should."

Why it matters: This is the gateway conversation. Almost every high earner suspects they're overpaying. They're right, but they don't know what to do about it. Their accountant files their return and tells them what they owe. Nobody is proactively looking for ways to reduce the number before it happens.

The dirty secret of the tax industry is that compliance and planning are two completely different services. Most accountants only do the first one. Your clients don't realize there's a second option.

How to open the door: "When's the last time someone actually looked at your tax situation proactively, not just filed your return, but mapped out strategies to reduce what you owe before year-end? Most people are surprised by how much is possible when you plan ahead instead of react."

What it's worth:The average proactive tax planning engagement generates $12,200 in fees. But more importantly, it opens every other door. Once you're talking about taxes, you're talking about everything: retirement, business structure, estate planning, investments. This is the conversation that unlocks the relationship.

2. The Business Entity Conversation

What to look for: Business owners operating as sole proprietors, single-member LLCs taxed as disregarded entities, or S-Corps that were set up years ago and never revisited. Anyone whose business has grown significantly since they chose their entity structure.

Why it matters: Most business owners pick an entity structure once, usually when they first started, and usually based on minimal advice. Then they never think about it again. But the right structure depends on income levels, growth trajectory, and tax law changes. What made sense five years ago might be costing them tens of thousands today. Self-employment taxes alone can eat up a large percentage of income. The difference between the wrong structure and the right structure can easily be $30,000+ per year for successful business owners.

How to open the door: "How long ago did you set up your business entity? It might be worth taking a fresh look at whether your current setup is still the most efficient."

What it's worth: Entity optimization is often the first domino. Once you restructure, you open the door to retirement plan strategies, compensation planning, and exit planning, all of which can potentially generate additional fees and deepen the relationship.

3. The "Beyond the 401(k)" Conversation

What to look for: High-income business owners already maxing out their 401(k) contributions who still have significant taxable income. Professionals or business owners earning $400K+ who are frustrated that retirement plan limits seem designed for people making far less.

Why it matters: The standard 401(k) contribution limit barely scratches the surface for high earners. But most don't know that cash balance plans, defined benefit plans, and other advanced retirement structures can allow contributions of $200,000-$300,000+ per year—all tax-deductible.

How to open the door: "I know you're maxing out your 401(k), but with your income level, that's really just scratching the surface of what's possible. There are retirement plan structures that can let you defer $200K or more per year. Has anyone walked you through what a cash balance plan or defined benefit plan could do for your situation?"

What it's worth: Cash balance plans and advanced retirement strategies typically involve setup fees of $3,000-$5,000 and ongoing administration. But the real revenue comes from managing the assets inside the plan, which can grow to seven figures quickly when contributions are $200K+ annually.

4. The Real Estate Tax Conversation

What to look for: Clients who own rental properties or commercial real estate worth $500K or more. Anyone who's mentioned an investment property, owns their business's real estate, or has real estate holdings beyond their primary residence.

Why it matters: Cost segregation studies accelerate depreciation on real estate, generating immediate, substantial tax savings. The problem is that most real estate investors either don't know cost segregation exists or assume it's only for large commercial properties. In reality, even residential rentals can benefit.

This is genuine low-hanging fruit. If you have clients who own rental properties, there's a good chance they're leaving money on the table simply because nobody has mentioned it.

How to open the door: "Have you ever had a cost segregation study done on your rental property? Most real estate investors I talk to either haven't heard of it or assumed it wasn't for them. But it can accelerate depreciation and generate significant tax savings in year one…often 5-8x the cost of the study itself."

What it's worth: Cost segregation studies typically generate 5-8x ROI for clients. The conversation also opens doors to 1031 exchanges, opportunity zone investments, and broader tax planning. One conversation about real estate often leads to comprehensive engagement.

5. The Capital Gains Conversation

What to look for: Anyone who's mentioned selling a business, investment property, or large stock position. Business owners approaching retirement. Clients with concentrated stock positions from company equity. Anyone who's said, "I'd sell, but the taxes would kill me."

Why it matters: Capital gains are often the biggest single tax event in someone's life. Business sales, real estate transactions, and stock liquidations can trigger federal, state, and net investment income taxes that approach 40% in some states. Yet most people don't plan ahead…they just accept the hit.

What they don't realize is that strategies like installment sales, opportunity zone reinvestment, charitable remainder trusts, and structured exclusions can defer, reduce, or eliminate significant portions of that liability. The key is planning before the sale, not after.

How to open the door: "If you ever decided to sell, have you thought through how you'd handle the tax hit? Most people assume they just have to pay it, but there are legitimate strategies that can defer or significantly reduce capital gains, if you plan ahead. Even if selling isn't imminent, it's worth knowing your options."

What it's worth: Capital gains planning on major transactions can save clients hundreds of thousands of dollars. The fees reflect the complexity and stakes involved. But beyond the immediate engagement, you're positioning yourself to manage the proceeds, which can mean significant AUM.

6. The Estate Tax Conversation

What to look for: Clients with net worth approaching $5M+ (individuals) or $10M+ (couples). Business owners whose company value, combined with other assets, could push them into estate tax territory. Anyone who hasn't updated their estate plan in the last 3-5 years.

Why it matters: The current estate tax exemption is historically high, but it's set to drop significantly in 2026. Clients who aren't planning for this change could see their estates hit with taxes they never anticipated.

One advisor working with a Virtual Family Office helped a client eliminate over $400,000 in future estate tax exposure while also putting asset protection in place…all from a single proactive conversation

How to open the door: "There's a window right now to lock in some strategies that could save your family significant taxes down the road. When did you last review your estate plan with an eye toward tax efficiency?"

What it's worth: Estate planning conversations open multiple revenue streams: life insurance to fund buy-sell agreements or estate taxes, trust structures that require ongoing administration, and the deepened relationship that comes from addressing legacy concerns. The value extends well beyond the immediate planning fees.

7. The Business Tax Credits Conversation

What to look for: Business owners who develop products, improve processes, or create software. Manufacturing companies, technology firms, engineering practices, and even businesses in industries that don't seem "innovative" but actually do qualify for R&D credits. Companies that have made significant capital investments or hired in targeted areas.

Why it matters: Tax credits are dollar-for-dollar reductions in tax liability…far more valuable than deductions. Yet most business owners don't realize they qualify. The R&D tax credit alone is worth billions annually, but a huge percentage of eligible companies never claim it because they assume "R&D" means laboratory research. In reality, developing new products, improving existing ones, creating custom software, or even experimenting with new manufacturing processes can qualify. The same goes for Work Opportunity Tax Credits, energy credits, and industry-specific incentives that most accountants never mention.

How to open the door: "Do you ever develop new products, improve your processes, or build custom software? A lot of business owners don't realize that kind of work can qualify for R&D tax credits—even if you don't think of it as 'research.' It might be worth having someone take a look. These are dollar-for-dollar credits, not just deductions."

What it's worth: R&D credit studies can recover significant tax dollars going back several years. The fees are typically contingent or based on a percentage of savings, making it easy to justify. And once you've identified one credit opportunity, you've established yourself as the advisor who finds money others miss.

The Bigger Picture

These 7 conversations have something in common: your clients aren't going to start them. They don't know what to ask for. They assume if there was a way to pay less in taxes, their accountant would have mentioned it. 

They're waiting for someone they trust to bring it up. That's the opportunity. The challenge is that most tax strategies require specialist expertise. Cash balance plans, cost segregation studies, R&D credits, these aren't things you can (or should) try to master yourself. 

That's where the Virtual Family Office model comes in: you stay in your lane, have relationships with specialists who handle the technical execution, and share in the revenue.

You don't need to become a tax expert. You just need to start the conversation. The advisors who are growing fastest right now aren't just adding more AUM clients. They're serving their existing clients more completely, uncovering planning opportunities that were always there, hiding in plain sight.

Elite Resource Team works with over 1,200 advisors to help them identify advanced planning opportunities and connect with specialists who can help execute them.