3 Questions to Ask Before Choosing a Personal Tax Advisor

(Plus 4 for your Tax Preparer)

Finding the right personal tax advisor can make a huge difference in your financial well-being. Ask these vital questions to make an informed decision.

With tax season squarely in the rearview mirror, now’s the perfect time to think about what you can do differently next year. Did you pay out a big chunk of money? Did you earn more in 2023, only to feel it when April rolled around? 

Before the sting wears off and you move on with your life, seek out a tax advisor to help you strategize for the coming year.

An individual meeting with a personal tax advisor to ask questions.

What to Ask When Seeking a Tax Advisor


1. “How do you define success as a tax advisor?”

This is probably the most important question, and there is really only one acceptable answer: To help you pay less tax.

The truth is, it’s rare to find a tax preparer that has tax reduction in mind—their goal is to file your taxes accurately and efficiently without thinking about strategy for the following year. Their top concern is keeping you square with the IRS.

But, if you want to really think about reducing your tax bill, you’ll need someone who can think about the bigger picture to help save you money in the long run—and that probably isn’t your CPA. 

2. “What are your credentials?”

The answer doesn’t need to be “CPA” or “12 years of accounting experience.” 

Tax advice shouldn’t necessarily come from your accountant, or even your tax preparer. It should come from someone who understands investing, strategy, and holistic financial wealth. 

In the case of Painless Tax Solutions, we believe we’re more qualified to advise you than your CPA because we build long-term, interdependent strategies across many financial avenues. A lot of tax-saving opportunities are achieved through specific investment activities that require licenses many CPAs do not have, which means that–even if your CPA offered great tax reduction advice–you’d have to call someone else to implement it.

Why not eliminate unnecessary layers and go straight to the experts?

3. “How do you communicate with your clients, and how accessible are you for questions or concerns?”

There’s no point being in a one-sided relationship with your tax advisor—you need them to be accessible.

At Painless Tax Solutions, we can meet with you in person (if you’re local), or anywhere in the world via phone or video call. We use a secure software called TitanFile where all your documents and questions are stored in one safe space.
Even better: If we file your taxes, we’ll use that same secure portal, keeping documents for taxes and strategy contained in one channel where you, your tax preparer, and your tax advisor can all see what’s going on in real time.

What to ask when seeking a tax preparer


1. Do you have a PTIN (Preparer Tax Identification Number)?

Here's something your tax preparer needs to have, but not your tax strategist: A PTIN. 

At Painless Tax Solutions, our team of top-notch preparers have PTINs who can sign tax returns, plus tax strategists who can assess your situation and offer strategy. It’s a win for everyone.

Ask a tax preparer to share what tax returns they've filed in the past before hiring them.

2. Have you prepared a (fill in the blank) tax return before?

This is a must-ask if you have a unique filing situation—and most people do, since nothing is one-size-fits-all. So be sure to ask your tax preparer if they have ever dealt with your specific circumstances and their approach to handling it.

3. What is your fee structure?

Transparency in pricing is crucial—nobody wants to get hit with an unexpected bill. Make sure your tax preparer is upfront about pricing; no hidden costs, no surprises. 

Painless Tax puts our clear pricing structure front and center on our homepage, so you won’t get blinded by a fee you didn’t know was coming.

4. What do you do post-return to look for potential tax reduction opportunities?

This is a big one, and the answer will most likely be “nothing.”

That’s where Painless Tax strategy begins. We can look at your return, analyze it, and show you how to reduce your bill in years to come. 

Key takeaway: Your CPA is not your tax strategist. 

We have nothing but respect for tax preparers, but their job isn’t to save you money. For that, seek out a tax strategist. And to find both in one convenient place? Hire Painless Tax. 


Book your free intro call with a tax strategist today, OR, get a high-level analysis of your 2023 tax return to find some quick and easy ways to save in 2024.

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