The Wealth Team Audit: 5 Questions Every Business Owner Should Be Asking Their Advisors

Most business owners have smart advisors.

But ask them when those smart people last spoke to each other, and things get awkward quickly.

I’ve had conversations with business owners where the CPA has one plan, the estate attorney has another, and the financial advisor is just…vibing with the S&P 500. They are all smart and well-intentioned, but no one is rowing in the same direction.

As a wealth manager, I’ve seen this play out too often:

Smart people giving smart advice that doesn’t add up to a smart strategy.

It’s not because anyone’s doing a bad job.

It’s because the system is built to treat each piece — tax, investments, legal, insurance, retirement — as if it exists in a vacuum.

But you don’t live in a vacuum. Neither does your business. And your wealth shouldn’t either.

That’s why I want to share something I call:

The Wealth Team Audit

Here are five questions every business owner should ask their advisors right now. If the answers aren’t clear — or worse, contradict each other — it may be time to get your team aligned.

1. “Are you communicating with the other professionals on my team?”

Most advisors don’t talk to each other unless someone (you) forces the issue. And that usually happens reactively — after a problem.

But real wealth planning isn’t reactive. It’s proactive.

If your CPA, attorney, and financial advisor have not shared notes recently, you are the system integrator.

That’s not where your energy should be going.

2. “What assumptions are driving your recommendations?”

Advisors often base their advice on implied assumptions, such as how much risk you’re willing to take, whether you’re planning to sell your business, or how much passive income you’ll need in retirement.

But if one advisor assumes a liquidity event in 3 years and another is planning for 15, your strategies will quietly diverge until something breaks.

Alignment starts with shared assumptions. Make them visible.

3. “Who’s thinking about how this fits together?”

Every advisor is a specialist. And that’s great — until it’s not.

You need someone who will look horizontally — across tax, estate, investments, business structure, insurance, and beyond.

Without that integrative view, you end up with a technically correct, but strategically inconsistent plan.

You need a strategist, not just specialists.

4. “If I sold my business tomorrow, what would break?”

This one’s powerful.

Most business owners don’t realize how much of their financial structure is anchored to the business, income, tax planning, benefits, legal entities, and even estate documents.

What happens if that foundation disappears?

Who’s helping you pre-wire your plan for a liquidity event — or even a forced exit?

5. “What does success look like to you, for me?”

This may be the most important question.

If your advisors say things like “outperforming the market” or “minimizing your tax bill,” they’re not wrong. But they’re probably not answering the fundamental question either.

Success isn’t just returns or savings — it’s freedom, peace of mind, and flexibility.

Does your team see that same target? Are they aiming for the same version of your ideal life?

If these questions made you pause — that’s normal.

But it’s also the sign of an opportunity.

The most successful business owners and families don’t just collect expert advisors.

They build teams that collaborate.

And when that happens?

You unlock not just better results but also better decisions, smoother transitions, and far fewer “how did that slip through the cracks?” moments.

If you’re a business owner who wants to build a coordinated wealth team — or a CPA, attorney, or advisor who wants to bring in trusted partners to better serve your clients — I’d love to connect.

Let’s build something better, together.

About the Author: I am a licensed advisor and member of the National Referral Network. I have been in the financial services industry since 2011. Over that time, I have successfully raised $42 million for several companies and completed my MBA. As part of the National Referral Network, my goal is to build financial teams for my clients, which will ensure that all the pieces of their financial puzzle work together. You can connect with me on LinkedIn.

Disclaimer: Although I am a licensed advisor, I am neither your advisor nor a certified public accountant (CPA) or Tax Attorney. Nothing discussed or shared should be taken as financial advice for any individual case or business situation. This information is for educational purposes only and is not intended to be tax advice or as an act of solicitation and/or recommendation to buy or sell any financial instrument.

🎙️ Professional Insight: Every Tuesday, I sit down with professionals from our network to have honest conversations about the challenges and opportunities business owners face every day. There is no fluff, no theory, just practical insight you can actually use. If you’re a business owner or care about one, subscribe to our YouTube channel so you never miss an episode that could move the needle.