The “90-Minute Per Quarter” Financial Pressure Test for Executives

What if all you had to do this week was pack your suitcase and relax on a beach? As financial advisors, it’s our job to help executives manage their complex financial situations and guide them in their decision-making process.  

At Hilltop, we believe that a unified financial strategy can help to alleviate decision-making fatigue, account for your time scarcity, and bring clarity. All you have to do is pack. Taking a quick quarterly financial pressure test can help to make finances feel simple, liberating, and better aligned with your goals. 

This pressure test isn’t about doing more financial work—it’s about protecting flexibility, reducing surprise, and staying ahead of decisions that matter. 

In 90 focused minutes, the pressure test can help you identify where risk may be quietly building, where concentration or timing could limit your options, and where a future decision is approaching without a plan. That awareness allows your advisory team to help do the heavy lifting—analyzing scenarios, coordinating across specialists, and preparing clear options—before urgency or stress sets in. 
 

The 90-Minute Per Quarter Executive Pressure Test 

⌚ Am I financially flexible right now? ☐ Yes ☐ No ☐ Unsure 

• If income stopped or changed tomorrow, would my lifestyle feel stable for at least 6 months? 

• Do I know—without logging in—roughly how much accessible cash I have? 

• Is there any upcoming expense or obligation I’ve been mentally postponing? 

⌚ Is too much riding on one outcome? ☐ Yes ☐ No ☐ Unsure 

• Would one company, one investment, or one market event materially change my plans? 

• Has my net worth become more tied to my employer or business over the last quarter? 

• If I stepped away from my role, would my financial picture feel exposed? 

⌚ Do I understand my next equity or compensation moment?
☐ Yes ☐ No ☐ Unsure 

• Do I know when my next vesting, exercise, or bonus decision occurs? 

• Would I feel confident explaining the tax impact in one sentence? 

• Am I reacting to equity events, or anticipating them? 

⌚ Am I creating avoidable tax stress? ☐ Yes ☐ No ☐ Unsure 

• Would a higher-than-expected tax bill surprise me this year? 

• Have any life or career changes occurred that could affect my tax picture? 

• Do I feel “behind” on planning, even if filings are done? 

⌚ If something happened to me, would my intentions be clear? ☐ Yes ☐ No ☐ Unsure 

• Have my family, assets, or responsibilities changed recently? 

• Do I assume my documents and beneficiaries are current—or do I know? 

• Would someone else be able to step in without confusion? 

⌚ What am I intentionally ignoring because it feels complex, uncomfortable, or time-consuming? (Fill in the blank) 

That answer is usually the reason to reach out. 

If you haven’t already established a financial advisor, now is a great time. A proactive approach to financial planning is always superior to crisis management. Hilltop Wealth Advisor’s seasonal schedule focuses on: 

GOAL TRACKING  | JAN-APRIL 

In our first meeting each year, we will help you reaffirm your priorities and measure progress toward your goals. This meeting typically covers: 

▶ Reviewing and updating goals 
▶ Net worth and cash flow 
▶ Savings and investment strategies 
▶ Stress test scenarios 
▶ Gifting strategies 

MID YEAR REVIEW  |  MAY-SEPT 

In our summer meeting, we will help you understand and prepare for different financial risks and will typically cover: 

▶ Risk management and insurance planning 
▶ Your estate plan 
▶ Legacy planning strategies 

TAX PLANNING  |  OCT-DEC 

In our final meeting of the year, we will review your income tax situation and consider strategies to manage what you owe: 

▶ Reducing current-year taxes 
▶ Minimizing future taxes 
▶ Pertinent tax code updates 
▶ Collaboration with your tax advisor 

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