A self-assessment for privately held business owners with $1 – 25 million in liquid or investable assets.

How to Use This Checklist

This checklist is not meant to diagnose problems. It’s designed to surface coordination gaps that often go unnoticed as businesses grow and personal wealth accumulates.
If you answer “not sure” to several questions, that’s normal. The uncertainty is often the blind spot.

Section 1: Cash & Liquidity Decisions

• Do you have a clear rationale for how much cash your business and personal balance sheet holds – and why?
• Is excess cash positioned intentionally, or has it accumulated by default?
• If market conditions change, do you know which cash you would deploy first – and why?
• Are business and personal cash reserves evaluated together, or in isolation?

Has anyone modeled the long-term cost of holding excess cash versus selectively investing a portion?

Section 2: Tax Coordination & Efficiency

• Are investment decisions coordinated with tax planning across multiple years?
• Do you actively manage gains and losses, or are taxes largely reactive?
• If you invested business or personal cash, would you know how tax harvesting could reduce future tax exposure?
• Are tax decisions optimized for both current income and future liquidity events?

Is there a clear strategy for smoothing tax liabilities rather than concentrating them in high - income years?

Section 3: Business vs. Personal Asset Alignment

☐ Are business and personal assets intentionally separated – or loosely commingled?
☐ Do entity structures support both operational needs and long-term personal planning?
☐ If the business value changed materially, would your personal plan adapt easily?
☐ Are personal investments diversified away from business risk in a deliberate way?
☐ Has anyone reviewed your personal balance sheet independent of the business?
Section 4: Advisory Coordination
☐ Is there a single advisor responsible for seeing how tax, investment, and liquidity decisions interact?
☐ Do your CPA, advisor, and attorney proactively collaborate – or operate independently?
☐ When a decision is made, is someone accountable for second – and third – order effects?
☐ Have you ever received conflicting advice with no clear way to reconcile it?
☐ Do you feel your advice team understands your full financial picture – or just their slice?
Section 5: Forward – Looking Readiness
☐ If an unexpected liquidity event occurred, would your structure be ready?
☐ Are investment and tax decisions made today aligned with long-term optionality?
☐ Do you have clarity on what “enough” looks like personally – not just professionally? ☐ Are planning decisions made intentionally, or postponed because “there’s not enough time?”
☐ Would you describe your current financial setup as flexible – or rigid?
Interpreting Your Answers
This checklist isn’t about perfection. Most successful business owners check “not sure” more often than they expect – especially around coordination, tax timing, and liquidity. That doesn’t mean something is wrong. It usually means decisions are being made in isolation instead of in sequence.
The biggest financial inefficiencies don’t’ come from bad decisions. They come from uncoordinated good ones.
Nex Step
If this checklist raised questions – or – confirmed concerns – it may be worth a structured planning conversation focused on alignment rather than products or performance.

A productive first discussion typically covers:
1) Cash and liquidity positioning
2) Tax coordination opportunities
3) Investment structure
4) Long-term flexibility and control

No commitment. No sales pressure. Just clarity

Wells Fargo Advisors Financial Network does not provide legal or tax advice.