Are you planning your taxes, or just filing them?
A 16-question diagnostic for business owners, executives, and families who want to keep more of what they earn. Answer on screen, see your readiness instantly, and print a branded result. Most tax is decided before the return is ever filed.
One point per Yes. Sixteen points possible.
The goal is not the number. The goal is finding the highest-leverage next move while there is still time to make it.
0-6
Reactive
Taxes are largely happening to you. Getting proactive is the highest-leverage move available.
7-12
Organized
A solid foundation. The gaps tend to be in coordination and multi-year strategy.
13-16
Strategic
You run taxes as a designed system. The work shifts to maintenance and new opportunities.
What we measure.
Proactive Planning & Visibility
Are your taxes planned year-round, or reconciled once a year? Most tax is decided before the return is ever filed.
Entity & Income Structure
Is the way you earn and hold income structured for after-tax results, or set by habit? Structure quietly drives the outcome.
Investment & Account Tax Efficiency
Are your investments and accounts working with the tax code? Asset location and account mix shape what you keep.
Multi-Year & Legacy Tax Strategy
Are you managing taxes across years and generations, not just this April? The biggest moves play out over time.
How to take it.
This is a diagnostic, not a verdict. The goal is clarity, and a better next move.
- Answer honestly. There are no trick questions.
- Three to five minutes is enough.
- Skip nothing. Each question is its own diagnostic signal.
- Your score lives only in your browser. No email required.
0 of 16 answered
Proactive Planning & Visibility
Year-round planning, not a once-a-year reconciliation.
This section looks at whether taxes are designed around ahead of time, or simply reported after the fact.
We review taxes proactively during the year, not only at filing time.
Planning windows are found before they close.
I know my approximate effective tax rate and how it has trended over the past few years.
You know the number you are actually trying to manage.
We can see income, deductions, and likely liability before year-end, while there is still time to act.
There is room to act, not just report.
Major future tax events are identified in advance, not discovered at filing.
Big items are seen coming, not found in April.
Entity & Income Structure
Entity choice, compensation, and income timing aligned for after-tax results.
This section checks whether the way you earn and hold income is structured on purpose.
Our entity structure (S-corp, C-corp, LLC, partnership, trusts) has been reviewed for fit with how the business actually operates today.
The structure matches how the business runs now.
Compensation, distributions, and owner benefits are coordinated for after-tax outcomes, not set by habit.
Owner pay is set by strategy, not inertia.
Retirement plan choices (401(k), cash balance, SEP, defined benefit) are sized to our income and aligned with our long-term strategy, even when those two pull in different directions.
Not just the biggest deduction today, but the right fit for the long-term plan.
The timing and character of income (ordinary versus capital, this year versus next) is something we manage on purpose.
When and how income lands is deliberate.
Investment & Account Tax Efficiency
Asset location, gain and loss management, account-type flexibility.
This section looks at whether your portfolio and accounts work with the tax code rather than against it.
Investments are located across account types (taxable, tax-deferred, Roth) with tax treatment in mind.
The right assets sit in the right account types.
We harvest losses and manage gains intentionally, rather than only at year-end.
Gains and losses are managed all year, not just in December.
We are intentional about our mix of account types (taxable, tax-deferred, Roth) and are working to shape it toward our long-term strategy.
Not just holding a mix, but deliberately improving it over time.
Concentrated or low-basis positions are identified and managed with the tax cost of selling in view.
The tax cost of selling is part of the plan.
Multi-Year & Legacy Tax Strategy
Multi-year bracket management, charitable strategy, and wealth transfer.
This section focuses on taxes across years and generations, not just the current filing.
We think about taxes across multiple years, not just the current filing.
Decisions weigh more than this year alone.
Roth conversions, bracket management, or income smoothing are evaluated when the window is favorable.
Favorable low-income or low-rate windows get used.
Charitable giving and gifting are structured tax-efficiently where appropriate (appreciated assets, donor-advised funds, or QCDs).
Giving is structured for impact and efficiency.
Estate, trust, and wealth-transfer plans are coordinated with the income-tax plan.
The estate plan and the tax plan speak to each other.
For informational and educational purposes only. This diagnostic is not individualized tax, legal, or investment advice. Tax rules change; verify with your own tax professional. Advisory services are offered through Whitwell & Co., an SEC-registered investment adviser.