How to Find the Right CPA (Before It’s Too Late)
Few things are more frustrating than working hard, making good money… and then losing it to the IRS or an unexpected lawsuit. That’s why two of the most important people on your business team are your accountant and your lawyer.
Having gone through the search process several times, I want to share some hard-earned lessons and give you a checklist that can save you time, money, and stress.
Before we dive in—if you’re a freelancer or web-based business owner, I highly recommend reading Accountant Showdown 2007. Matt’s post was a gem I found while researching this topic, and his personal narrative hits the nail on the head.
The 5 Keys to Choosing the Right CPA
1. Reputation
Good news travels fast. Bad news travels faster.
Ask around—fellow business owners, attorneys, even your local IRS agents. Who do they trust with their books? After a few conversations, you’ll start to see names repeat. That’s a good sign.
When we needed a lawyer, we asked four local contacts. All four recommended the same person. No contest. She’s now a trusted advisor and key player on our team.
Once you have a shortlist, start interviewing. If a CPA doesn’t have time to talk now, they won’t make time when you really need them.
2. Communication
Your accountant is not a lone wolf—they’re part of your team.
They should protect your assets and help you understand what’s going on with your finances. If they can’t explain things in plain English or aren’t interested in teaching you a little along the way, walk away.
You need someone who can meet you at your level. Whether you’re a beginner or a seasoned business owner, good communication ensures you’re making smart, informed decisions.
3. Guidance
A good accountant is more than a glorified bookkeeper. They’re a strategic advisor.
They should help you with:
- Tax planning
- Choosing the right business structure
- Handling contractors vs. employees
- Deciding how much to pay yourself
- Managing cash flow and deductions
Ask questions in the interview:
“Have you worked with freelancers?”
“Are you familiar with online or service-based businesses?”
“Can you walk me through how I should handle estimated taxes or write-offs?”
You’re not just looking for a number cruncher—you want a guide.
4. Availability
Can you actually reach them?
If it takes your accountant a week to return a call or email, your business will suffer. Ask up front:
- What’s your average response time?
- Can I call you with quick questions?
- How fast can you book me in for a meeting?
Our current accountant is great at everything—except this. His guidance is gold, but it’s frustrating how hard he is to reach. Honestly, it may end our working relationship eventually.
5. Protection
A major role of any CPA is defending you in the event of an IRS audit.
Ask how much experience they have with audits. Have they ever represented clients in front of the IRS? Have they ever been an auditor?
Ours spent over a decade as an IRS auditor—knows the system inside and out. That’s the kind of experience you want in your corner.
50 Smart Questions to Ask When Interviewing a CPA
These questions will help you vet a potential accountant thoroughly. Don’t feel like you need to ask all of them—but picking the right ones for your situation can reveal a lot.
Background & Experience
- What licenses do you have?
- How long have you worked in accounting?
- Do you specialize in small businesses or freelancers?
- What’s your experience with online/service-based businesses?
- Have you ever worked with clients being audited?
Fees & Structure
- How do you calculate your fees?
- Do you offer flat-rate packages or customized services?
- Who in your firm will I be dealing with regularly?
- Do you outsource any work?
Working Style
- How quickly do you return calls/emails?
- Do you take walk-ins or scheduled appointments only?
- What’s your average turnaround time on taxes?
Technology & Tools
- Are you tech-savvy?
- What accounting software do you recommend for someone like me?
- Do you know how to use [insert your preferred software]?
Tax Knowledge
- What tax laws changed this year that impact me?
- What deductions am I eligible for?
- How do you help clients maximize tax savings?
- Can you help with 1099s and subcontractor issues?
Business Strategy
- Can you help me decide on my business structure (LLC, S-Corp, etc.)?
- What are the red flags you see in businesses like mine?
- How do you approach estimated taxes?
- What should I be doing now to prepare for growth?
Personal Fit
- What do you love about what you do?
- What’s your ideal client?
- What’s your privacy policy?
- Do you work with financial planners?
- Do you do your own accounting?
Miscellaneous & “Gut Check”
- Can I write off [insert expense here]? (e.g., iPhone, business suit)
- What happens if I get audited?
- What are some of the biggest messes you’ve helped clean up?
- Is there a question I should have asked but didn’t?
Final Thoughts
Getting the right accountant isn’t just about staying legal—it’s about protecting what you’ve built, optimizing your decisions, and setting yourself up for long-term success.
Whether you’re just starting out or growing fast, the sooner you build this relationship, the better.
Now it’s your turn:
What questions have you asked when choosing an accountant? What have you learned from good—or bad—experiences? Drop your thoughts in the comments.
Let me know if you want this turned into a downloadable guide, PDF checklist, or email series—you’ve got a solid resource here that could be super valuable to your audience.