Summary of What This Blog Covers
- Six key tax questions to ask your CPA every quarter.
- How to catch missed deductions and reduce audit risk.
- Why your entity and state tax status may need updating.
- The value of proactive, strategic CPA support year-round.
Let’s play a game.
You walk into your CPA’s office (or, more realistically, hop on a Zoom call) and they ask how things are going. You give them the half-smile that says, “Please don’t look too closely at my books.” Then you hit them with the go-to line:
“So… am I good?”
Cue the awkward silence.
Because here’s the truth: “Am I good?” is not a tax plan. It’s a wish. It’s the business equivalent of driving with your check engine light on and hoping your car just sorts itself out.
Tax planning isn’t just about making sure you’re not in trouble. It’s about making moves, asking the right questions, and using your CPA as a strategist not just a number-slinger with a filing deadline.
If you’re running a business, especially in the freelance, consulting, or creative space, this post is your wake-up call. It’s time to swap the vague questions for the real ones, the ones that actually move the needle.
Let’s walk through the 6 tax questions that will turn your CPA meetings from reactive cleanups into proactive strategy sessions. And yes, we’re keeping it sharp, helpful, and maybe just a little entertaining because taxes don’t have to be boring. They just have to be right.
1. What Changed in Tax Law This Year That Actually Affects Me?
Tax laws change. Every. Single. Year.
But unless your CPA is breaking it down in a way that doesn’t sound like a C-SPAN transcript, you’ll miss something important.
Here’s what most people think:
“If it was important, QuickBooks would’ve told me.”
Spoiler: QuickBooks is not your accountant. It’s a smart calculator. It doesn’t know that you’re now eligible for a new deduction or that the mileage rate increased. It just tracks what you put in.
Your CPA, on the other hand, is the person who should know what’s changed and how it applies to you but only if you ask.
Ask this:
- What IRS updates, thresholds, or deadlines changed for 2025?
- Are there any new deduction caps, income brackets, or phaseouts I should be aware of?
- Has anything changed for 1099 filers or small business owners that impacts me?
If your CPA in Austin, Texas or certified CPA near you doesn’t have a clear, confident answer? You might want to check if they’re stuck in 2022.
2. Are There New Credits or Deductions I Should Know About (That I Might Be Missing)?
This question is the difference between coasting through tax season and walking away with serious savings.
Because let’s be real: most of us know about the basics. Home office, mileage, maybe the occasional travel deduction if we remembered to save receipts.
But what about the Qualified Business Income Deduction? Or the Augusta Rule? Or deductions related to retirement contributions, energy efficiency, or Section 179 depreciation?
Ask this:
- Are there any credits I now qualify for based on my income or business activity?
- What deductions did I miss last year that I can still claim or carry over?
- Is there anything I can do before the end of the year to lock in extra savings?
Aha moment: If your CPA just runs your numbers and files without asking what’s changed in your life or business, you’re working with a tax preparer not a strategist.
A real tax professional near you or licensed CPA knows that the best way to save money is to plan ahead and not fix things in April.
3. Should I Revisit My Business Entity Structure Before Year-End?
You might’ve set up an LLC the moment you got your first contract. You felt official. You got the logo. You even Googled “Do I need an EIN?” and high-fived yourself when you figured it out.
But here’s what no one tells you: the way your business is taxed matters a lot more than what it’s called.
And it may be time to upgrade your structure.
Ask your CPA:
- Would switching to an S Corp reduce my self employment tax?
- Should I change from single-member LLC to partnership or C Corp?
- What would this change do to my take-home income and tax liability?
Entity changes can help you:
- Save thousands in taxes
- Improve audit protection
- Prepare for team expansion, investments, or loans
But they require planning. You can’t switch structures mid-March and hope it helps your 2025 tax return.
If your tax advisor near you or chartered public accountant hasn’t run this analysis with you lately, now’s the time.
4. Do I Owe State Taxes Somewhere I Didn’t Plan For?
State taxes are like bad exes. Ignore them, and they show up with penalties and drama.
And thanks to remote work, e-commerce, and hiring contractors across state lines, it’s easier than ever to accidentally create nexus in a state you didn’t even know you were doing business in.
Ask your CPA:
- Do I need to register for sales tax in other states?
- Am I responsible for state income tax based on where I sell or serve clients?
- Should I be filing any franchise tax returns?
These questions are especially important if you:
- Sell digital products or services
- Hire out-of-state contractors
- Travel often for client work
- Use platforms like Shopify, Amazon, or Stripe
Your Austin accounting service or certified public accountant near you should be tracking this. And if you’re trying to DIY it with tax software? That’s a fast track to trouble.
5. When Are My Estimated Payments Due and How Much Should I Send?
If you don’t know your next estimated tax payment due date, don’t worry. Most people don’t.
But here’s the deal: skipping or underpaying can result in penalties from the IRS. They’re not harsh, they’re just very consistent.
If you’ve ever received a surprise tax bill with “penalty” in bold, this one’s for you.
Ask your CPA:
- What do I owe this quarter based on my actual 2025 numbers?
- Can we adjust my 1040-ES payments to avoid overpaying?
- Am I on track for my self-employment tax and federal obligations?
If your income fluctuates, don’t just copy-paste last year’s numbers. Let your certified public accountant near you run fresh estimates that reflect your reality, not last year’s wishful thinking.
6. What’s My Risk of Audit and How Do We Minimize It?
Audits are like dental emergencies. No one wants them. But if one’s coming, you’d better have your paperwork ready.
Most audits are triggered by sloppy filings, unrealistic deductions, or mismatched records. And once the IRS sees something weird, they start digging.
Ask this:
- Do any of my 2025 deductions raise red flags?
- Is my documentation strong enough to back up my return?
- Are there any risky areas in my reporting?
Your taxation accountant or CPA office near you should help you build an audit-ready defense:
- Monthly reconciliations
- Properly categorized expenses
- Clean documentation
- Clear logs for mileage, home office, and subcontractor payments
Remember: the goal isn’t to avoid attention, it’s to be so prepared it doesn’t matter if the IRS takes a closer look.
Bonus Question: Are You Reviewing This With Me Every Quarter?
This one’s the mic-drop.
If your CPA is only reaching out once a year, or if you only hear from them when it’s time to sign your return, you’re getting shortchanged.
Ask this:
- Can we do quarterly check-ins to review tax strategy, compliance, and upcoming changes?
A real small business CPA that is Austin-based or tax consultant near you will be excited you asked.
Quarterly reviews give you time to:
- Fix mistakes before they cost you
- Adjust strategy while you still have time
- Prepare for tax season with zero surprises
If your current CPA isn’t on board? You’ve got options. And we know a few people.
Ready to Ask Smarter Questions?
You’ve made it this far, which means you care enough to get this right. That’s half the battle.
Now it’s time to turn information into action.
At Insogna, we don’t just file your return. We help you ask the right questions, build smarter systems, and stop throwing away money on mistakes and missed opportunities.
We’re a proactive, CPA-led Austin accounting firm that helps business owners across industries get ahead of tax season not buried under it.
Use this checklist in your next CPA meeting or better yet, let us walk you through it.
- Smarter questions
- Real strategy
- No panic
- Just clarity, action, and results
Book a call with Insogna today.
Ask better questions. Get better answers. And finally, feel good about tax season.
Frequently Asked Questions:
1. What should I ask my CPA besides “Am I good?”
Swap the vague check-in for smarter questions:
- What changed in tax law this year?
- Am I missing any deductions or credits?
- Should I change my entity structure?
Your CPA in Austin, Texas should turn your questions into strategy, not just compliance.
2. Can QuickBooks handle my tax strategy?
Nope. QuickBooks tracks expenses. It doesn’t catch missed deductions, entity election opportunities, or help plan for self employment tax. That’s why working with a certified public accountant near you still matters.
3. Do I owe state taxes in other states?
If you’re selling online or hiring contractors out of state, maybe. Ask your tax consultant near you to check for state nexus. Ignoring this could mean surprise tax bills and penalties.
4. Do I really need to revisit my entity structure?
Yes. Revenue shifts. Strategy should, too. Your small business CPA in Austin can tell you if an S Corp switch could save thousands in taxes this year.
5. How do I avoid an IRS audit?
Keep records clean, label expenses clearly, and work with a tax accountant near you who knows what the IRS looks for. A little prevention now saves a lot of pain later.