The Tax Corner: Are You Asking the Right Questions?

You Had the Meeting. But Did Anyone Actually Execute the Plan?

Most business owners leave planning meetings feeling good. The conversation was sharp, the ideas were solid, and everyone seemed aligned.

Then October arrives and nothing has been done. The whole year — and every opportunity in it — is gone.

Design vs. Structure: Where Planning Actually Starts

Brian Hartstein opens with a framework that applies to every area of business owner planning: design versus structure. Design is everything specific to your business — your goals, your entity setup, your benefit plan provisions, your tax situation. Structure is who executes each piece of that design so the implementation actually gets done.

Most planning conversations jump straight to structure without ever getting the design right. That is where the gaps live.

Multiple Entity Planning: What It Is and Why It Matters

If you own more than one business entity — or if your business owns real estate — you are already in multiple entity territory. The rules that govern how those entities interact for benefit planning purposes can either open up significant planning opportunities or quietly close them off.

For businesses in hard hat industries like construction and real estate, ownership percentage dictates where planning can happen. These are called control group rules. For service businesses — legal, medical, architecture — there is a second layer called affiliated service group rules that are even more complex.

Does Your Business Own Its Building? Read This.

One of the most common and overlooked planning gaps Andrew and Brian see: a business that owns its own building inside the same entity that runs operations. It feels simple. It is actually a liability exposure and a missed opportunity.

Separating the building into its own LLC can protect against liability, create depreciation planning options, and — critically — preserve flexibility for an eventual business sale. Private equity buyers typically want the operating business, not the real estate. If the building is inside the same entity, stripping it out at sale becomes a tax problem.

Benefit Plan Design: The Details That Cost You Money

Once entity structure is addressed, the next layer of questions is about benefit plan design. This is where most business owners — and many advisors — leave real money behind.

Brian walks through several areas where the wrong plan design creates unnecessary cost. One example: if your 401(k) has a three-month eligibility requirement but your average employee turnover happens at 5.7 months, you are funding benefits for people who will never vest. A six-month eligibility saves money immediately.

Another: recordkeeping fees inside the plan. Business owners typically hold the largest balances. Reducing fees by even 25 basis points over a decade on a $1 million balance is real money — money that stays in the owner's account instead of going to a provider.

For a deeper look at where 401(k) plans fall short for higher earners, see our blog on why 401(k) strategies often fail high earners and our video on understanding your 401(k) plan documents.

Qualified vs. Non-Qualified Plans: Knowing the Difference

Qualified plans — 401(k), defined benefit pension, profit sharing — give you the tax deduction in the year you make the contribution. For business owners who need deductions today, these are typically the priority.

Non-qualified plans do not generate an immediate deduction, but they offer flexibility that qualified plans cannot. You can select which employees to reward, create retention incentives with vesting schedules, and structure compensation in ways that tie key people to the business. The right answer depends on your goals — and it is a question worth asking explicitly.

If Roth planning is part of your overall strategy, our complete guide to Roth conversions covers how timing, tax brackets, and income thresholds work together.

The 2026 Roth Catch-Up Rule: A Compliance Issue, Not Just a Planning One

Under SECURE Act 2.0, any employee — including the business owner — who earned more than $145,000 from the entity in the prior year and is age 50 or older must direct their 401(k) catch-up contributions to the Roth portion of the plan. Pre-tax catch-up contributions are no longer allowed for highly compensated employees.

If your plan does not have a Roth provision, those employees cannot make catch-up contributions at all. Most providers can add the Roth option quickly, but it requires a plan document amendment through your third-party administrator. The time to do this is now — not when an audit surfaces the issue.

For a full breakdown of this rule and what plan sponsors need to do, watch our video on the new Roth 401(k) catch-up rule for high earners. For broader context on SECURE Act 2.0 changes, see our blog on 6 ways SECURE Act 2.0 may impact you.

If the Advisor Does Not Drive It, It Does Not Get Done

The through line of both episodes in this series is the same: strategy without execution is just a conversation. The financial advisor's job is not only to identify the opportunities — it is to lead the process that turns those opportunities into outcomes.

That means setting up the joint meeting with the CPA instead of leaving it to the client. It means following up in Q3 instead of waiting for Q4. It means being the mortar between the bricks — the piece that binds the CPA, the attorney, and the financial plan into something that actually moves.

For a deeper look at how the Four Corners framework applies to your business overall, visit our Part 1 episode on building your advisory team and knowing their roles . If you are also evaluating your CPA relationship, Episode 121 on choosing a CPA and the questions business owners should be asking is a natural next listen.