How to Find a Tax Strategist Who Actually Saves You Money
Let’s start with the truth:
Most tax professionals are not tax strategists. They’re historians. Documenting the past. Filing returns. Minimizing audits.
But if you're a business owner or high-income earner looking to maximize what you keep, what you reinvest, and what you pass on, you need more than compliance. You need someone who plays offense.
That’s where a tax strategist comes in.
And if you find the right one, it could mean tens or even hundreds of thousands in tax savings every single year.
Here’s exactly how to find them.
1. Know What a Tax Strategist Is (and Isn’t)
First, clarify the role. A tax strategist is not just a CPA. In fact, many CPAs are compliance-focused by default.
A true strategist:
Looks at your full financial picture, not just your numbers from last year.
Designs a multi-year tax plan aligned with your business and life goals.
Brings proactive ideas before December 31.
Knows how to leverage structures like trusts, entities, and insurance for tax efficiency.
They don’t just prepare returns. They engineer outcomes.
If your current tax pro isn’t doing that, they’re not a strategist.
2. Prioritize Strategy Over Credentials
Let’s debunk a myth: credentials aren’t strategy.
Yes, you want someone experienced. Licensed. Ethical. But don't confuse credentials with strategic ability.
The best strategists:
Think creatively and legally at the same time.
Speak the language of business, not just tax code.
Know how to implement, not just recommend.
Coordinate with your financial advisor, not work in silos.
Ask yourself: Are they checking boxes? Or architecting outcomes?
3. Look for Proactivity
If your current tax advisor only contacts you in Q1, they’re too late.
Great tax strategists:
Meet quarterly or at major inflection points (e.g. business growth, asset purchases, exits).
Help you time income and expenses for strategic advantage.
Discuss entity structure, compensation design, retirement planning, and more, all before filing season.
Ask them: “What do you do to help clients before year-end?”
If their answer is vague or reactive, keep looking.
4. Ask How They Get Paid
Here's where things get real.
Many tax pros are built around a volume model. File more returns, faster. That doesn’t lend itself to high-touch, strategic service.
Strategists often:
Work on retainer or flat-fee structures.
Charge based on value delivered or savings created.
Have separate fees for compliance vs. strategy.
Yes, a strategist may cost more up front, but the ROI is measured in how much you keep, not what you pay.
A $10,000 tax strategist who saves you $80,000 is a no-brainer. A $1,200 CPA who keeps you overpaying the IRS? That’s expensive.
5. Review Their Process, Not Just Their Personality
Charisma is great. But your tax pro doesn’t need to be your best friend.
What you need is a repeatable process:
Do they have a structured discovery phase?
Do they request forward-looking data (not just past returns)?
Do they deliver a written plan?
Do they collaborate with your financial or legal team?
A strategist with a defined process is far more valuable than one who “just figures it out as we go.”
6. Ask the Right Questions
Here are a few revealing questions to ask in your initial meeting:
“Can you share an example of a client like me where you saved them five figures or more?”
(If they can’t, they’re not playing at your level.)
“How do you coordinate with a financial advisor or estate attorney?”
(Lack of coordination = missed opportunities.)
“What strategies would you typically consider for a business owner earning $500k+?”
(You're not looking for free advice—just to hear how they think.)
Their answers will tell you whether they’re worth a second call.
7. Look for Industry Alignment
If you’re a dentist, tech consultant, or real estate developer, your world isn’t generic. Your tax strategy shouldn’t be either.
Ask:
Do they specialize in your industry?
For our business owners, do they understand cash flow cycles unique to your business?
Have they worked with others like you before?
Industry-specific knowledge often unlocks industry-specific savings.
8. Watch for These Red Flags
“Let’s just see how the year ends up.”
(That’s reactive, not strategic.)
“There’s nothing more we can really do at your income level.”
(Run. Fast.)
They recommend only retirement plans and deferral tools.
(Saving taxes isn’t just about deferral. It’s about design.)
They push products before strategy.
(Focus on your goals, not their commission.)
9. Don’t Settle for the Default
Most people get their tax pro from one of three places:
Their parents
A friend’s referral
The first person who said yes
But your income isn’t average. Your tax approach shouldn’t be either.
Upgrading your tax strategy can unlock more savings than almost any investment or product you’ll ever buy. It’s worth vetting carefully.
10. Ask Us to Help You Build the Right Team
At Pfister Financial, we don’t prepare taxes. But we know what to look for in those who do.
We help clients:
Build a comprehensive wealth ecosystem.
Plug cash flow leaks and tax inefficiencies.
Connect with vetted, proactive tax strategists who think like business owners and high-income earners.
If you're ready to stop bleeding six figures to the IRS unnecessarily, we can help you find the right pro to do something about it.
Ready to start saving strategically?
Download our free Tax Navigator Guide and learn the advanced strategies top tax pros use to help business owners legally minimize their tax bill. Inside, you’ll discover how to classify income more efficiently, leverage deductions most advisors miss, and make tax decisions that support your bigger goals.
