Most business owners treat their attorney the way most people treat their dentist: somebody you call when something already hurts. They set up their entity years ago. They created a buy/sell agreement at some point. They wrote a will after their last kid was born. Then everything went in a drawer and stayed there.
Meanwhile, their business has tripled in value. The partners have changed. Tax law has shifted multiple times. The kids are adults. And the legal documents that are supposed to protect their family, their company, and their wealth are quietly out of date, often by a decade or more.
This is the same dynamic we wrote about in our blog on the 7 tax conversations advisors should be starting. Compliance is what most clients have. Planning is what they need. The gap between the two is your opening.
The opportunity isn't for you to become a lawyer. It's to be the advisor who notices what nobody else is noticing, and brings in the right specialist before a crisis, a missed window, or a transaction locks in suboptimal results.
Here are 3 legal conversations you can have with clients right now, and the language to open the door.
1. The "When Was Your Last Legal Audit?" Conversation
What to look for: Business owners with companies worth somewhere between $2M and $1B. Especially those who set up their entity, buy/sell agreement, and operating documents years ago and haven't touched them since. Bonus signals: meaningful growth since formation, partner changes, key employees added, family shifts (marriage, divorce, kids entering the business), or a recent unsolicited offer from a buyer.
Why it matters: Most business owners haven't had their core legal documents reviewed in five-plus years. The buy/sell agreement was drafted when the company was worth a fraction of what it's worth today. The operating agreement doesn't reflect the current ownership structure. The estate plan doesn't account for the company's current value. Every one of those gaps is a landmine: if a partner dies, gets divorced, becomes disabled, or simply wants out, the documents in place may not work, may not be enforceable, or may trigger a tax disaster nobody saw coming.
A legal audit surfaces those issues before they become crises. It's the equivalent of preventive maintenance, far cheaper than waiting for the breakdown, and almost always reveals at least one thing the owner didn't know was a problem.
How to open the door: "When was the last time anyone reviewed your legal documents together, not one piece at a time, but your entity structure, your buy/sell, your estate plan, and how they all interact? A lot of business owners I talk to haven't had that done in years, and a lot has changed in the meantime. Probably worth a fresh look?"
2. The Comprehensive Estate & Wealth Structuring Conversation
What to look for: Clients with $25M+ in net worth, rapidly growing business owners trending toward that level, or families whose multi-generational assets aggregate to that line. Especially clients who have a "good enough" estate plan from five or ten years ago and haven't revisited it. Anyone who's mentioned wanting their wealth to outlast them, support multiple generations, fund philanthropy, or protect against creditors and lawsuits.
Why it matters: At this level of wealth, the difference between an off-the-shelf estate plan and a comprehensively designed structure is generational. Asset protection, income tax minimization, estate tax minimization, generation-skipping tax planning, business succession, philanthropy, preparing the next generation…these aren't separate problems. They're one integrated puzzle, and they need to be designed together by people who do this every day.
One thing makes this conversation especially urgent right now. Asset protection, which is dramatically harder to put in place after a claim than before, is something most high-net-worth clients have never been walked through. Most assume "I have an LLC" is asset protection. It usually isn't.
How to open the door: "Has anyone ever taken a step back and looked at your wealth holistically, not just the investment side, but how it's structured for asset protection, how it transfers to the next generation, what the tax exposure actually looks like across all of it, and whether your current plan still fits where you're heading? Most people at your level have never had that kind of comprehensive review, and the ones who have done it are usually surprised by what comes up."
3. The Pre-Sale Business Planning Conversation
What to look for: Business owners thinking about selling in the next one to five years. Especially: owners who've received unsolicited offers, owners approaching retirement, owners whose business has grown to where a sale would be life-changing, partners with friction who may eventually need to separate, or anyone who has said "I'd sell at the right price" or "I'm probably three to five years from exit."
Why it matters: The single biggest determinant of how much money a business owner keeps from a sale isn't the deal terms, it's what was done before the LOI was signed. By the time a transaction is in motion, most of the best planning options are off the table. Trusts, gifts, ownership restructuring, charitable strategies, generation-skipping techniques…all of these are vastly more powerful (and some are only available at all) when implemented well in advance of a sale.
The owner who plans two to three years ahead routinely keeps materially more of the proceeds than the one who waits. On larger transactions, that gap can run into seven and eight figures. And these aren't aggressive or experimental strategies, they're the same well-established structures family offices have been using for decades. Most business owners have just never been told they apply to them.
How to open the door: "If you ever decided to sell, even if it's years away, how the deal is structured matters a lot less than how your ownership is structured before the deal happens. Most of the best planning has to be in place well in advance. Have you and your CPA ever mapped out what a sale would actually look like after all the taxes, and what could be done now to change that number?"
The Bigger Picture
Just like with tax, your clients aren't going to start these conversations on their own. They don't know what they don't have. They assume that if something were wrong with their entity, their attorney would have flagged it. They assume their estate plan still works. They assume the buy/sell they signed eight years ago still reflects what they actually want.
It rarely does. The only reason most of them haven't faced a crisis is that nothing has triggered one, yet.
This is where the Virtual Family Office model does the heavy lifting. You don't need to become a lawyer. You don't need to learn how to design a dynasty trust, audit an operating agreement, or model a pre-sale structure. You just need to recognize the signals, ask the opening question, and bring in a specialist who can execute the technical work.
The advisors growing fastest right now are the ones noticing what their clients haven't asked about, and starting the conversation anyway. Elite Resource Team works with over 1,200 advisors to help them identify advanced planning opportunities and connect with specialists who can execute them.
