TMA Accounting Blog

8 Questions to Ask When Shopping for a New Accountant

Written by Jonathan Lindorf | July 10, 2025

Imagine this: It’s late February, and tax deadlines are right around the corner. You email your accountant—again—asking for clarity about a deduction or document, and all you get is radio silence or a confusing reply. The clock is ticking, your stress is rising, and you wonder if it’s time for a change.

If that scenario feels all too familiar, you're not alone, and you’re not wrong to start looking for better help.

Choosing the Right Accountant

Choosing the right accountant is more than a business decision; it’s a collaboration. Your accountant should be more than a form-filler or number cruncher. They should help you keep your business on track year-round, bring clarity to your financial decisions, and free you to focus on what you do best. At their best, accountants act as trusted advisors helping you grow, stay compliant, and sleep better at night.

However, not every accounting firm is equipped to do that. And in the chaos around tax time or during a big business decision, you don't want to discover that you’ve been working with the wrong fit.

So, how do you find an accountant who truly has your back?

Start by asking the right questions. The answers will be revealing, and not just about their services, but about how they think, how they work, and whether they’ll help you simplify the complex world of business ownership.

1. What Services Do You Offer Beyond Tax Preparation?

Tax filing is important, but it’s only part of what an accountant should do. If you're only getting help once a year, you're missing out.

Today’s small business owners face challenges that go far beyond filing a return. Cash flow, payroll, compliance, reporting—it’s a lot to manage. That’s why you want an accountant who’s not just a once-a-year tax preparer, but an all-year guide.

Ask if they offer ongoing services like:

  • Bookkeeping
  • Payroll processing
  • Financial reporting
  • Business advisory

A great accountant is more than a form-filler; they’re part of your team. They help you stay organized, meet deadlines, avoid expensive mistakes, and run your business with clarity and confidence.

If you’re only hearing from your accountant at tax time, it might be time to find someone who’s with you for the whole journey.

2. Do You Specialize in My Type of Business?

Would you hire a dentist to fix your car? Probably not. In the same way, your accountant should understand your industry.

Different businesses have unique needs. Restaurants have complexities around labor, food costs, and tips. Medical practices may deal with insurance payments. Trades like electricians or plumbers need help tracking materials, labor, and job costs.

An accountant who works with businesses like yours will be familiar with best practices, common problems, and hidden opportunities. That kind of industry-specific knowledge can save you time, money, and headaches.

3. How Will You Help Me Stay Compliant and Avoid Surprises?

Let’s face it, running a business means juggling a mountain of rules and deadlines. One missed form or forgotten tax can result in fines, penalties, or even legal consequences. With compliance requirements constantly changing, it’s challenging to keep up.

Your accountant should be your first line of defense against penalties. Ask how they help clients stay on top of deadlines and rule changes. For example:

  • Do they send reminders about due dates?
  • Do they help you set up systems to track expenses and payroll?
  • Will they help you file required forms like 1099s or sales tax returns?

You want someone who helps you avoid surprises, especially the unpleasant and expensive ones. Having this peace of mind helps you focus on running your business.

4. How Is Your Pricing Structured?

Nobody likes surprise bills, especially when they come from your accountant.

Before you sign on with an accountant, ask for a clear explanation of how they charge for their services:

  • Do they charge by the hour, offer flat fees, or monthly packages?
  • What’s included in that pricing, and what might trigger additional costs?
  • Will you be charged extra for phone calls, emails, or help responding to an IRS notice?

Many business owners prefer fixed-fee pricing because it simplifies budgeting. Just make sure you understand what services are part of that fee. If you call with a question, will that be extra? If the IRS sends you a notice, is that support included?

Clarity up front builds trust and helps you avoid awkward money conversations later.

5. What Is Your Approach to Communication and Responsiveness?

Let’s be honest, good communication is one of the biggest reasons business owners either love their accountant… or start shopping for a new one.

An accountant should never feel like a black hole where emails go to die. You deserve timely answers, clear explanations, and a consistent point of contact.

Ask questions like:

  • How quickly do you respond to emails, phone calls, or client questions?
  • Will we have scheduled check-ins, like monthly or quarterly meetings?
  • Who will I work with directly? The same person each time, or a rotating team?

Some accountants disappear outside of tax time. Others make you feel like your success actually matters to them. You want an accountant who matches your communication style and who’s available when it counts.

After all, you’re trusting them with your business finances. You should feel confident that they’ll be there when you need guidance, not just when they need a signature.

6. What Technology Do You Use, and Do I Have to Learn It?

Accounting technology should make your life easier, not turn your business into a tech support hotline.

The right tools can simplify everything from tracking expenses to running payroll to reviewing clear, timely financial reports. However, not all accountants use the same systems or utilize them effectively.

Here’s what to ask:

  • What accounting software do you use? (QuickBooks, Xero, or something else?)
  • Will I need to learn and use that software myself, or will your team handle most of it?
  • Do you offer training or support if I need to use it?
  • Can you automate tasks like invoicing, payroll, or financial reporting?

Look for an accountant who uses modern, secure tools to save you time and reduce stress. Even better? One who can take those routine financial tasks off your plate entirely so you can focus on running your business instead of wrestling with spreadsheets.

7. How Will You Help Me Understand My Numbers?

Financial reports are only helpful if you actually understand them.

Too many business owners get handed a stack of reports full of jargon and numbers, but no context. A great accountant goes beyond the data. They help you interpret what it all means and how to use it to make better decisions.

Ask them:

  • Can you explain reports in simple terms?
  • Will you help me understand my cash flow?
  • Do you highlight any trends or warning signs that I should be aware of?
  • Will you proactively review my numbers so I know how my business is really performing?

The goal isn’t just to stay compliant, it’s to run a smarter, more profitable business. Your accountant should be a translator and a guide, helping you connect the dots between the numbers and the decisions you face every day.

8. Can I Speak to Some of Your Current Clients?

Online reviews can tell you something, but nothing beats hearing straight from someone who’s already walked the path you’re about to take.

A reputable accountant should have no problem connecting you with a few long-term clients who are willing to share their experience.

When you talk to them, ask:

  • What do you like most about working with this accountant?
  • Have there been any surprises, good or bad?
  • How have they helped your business grow, stay compliant, or solve problems?

These conversations can offer powerful insights that no brochure or website can. They help you understand what it’s really like to work with this accountant day in and day out, and whether they deliver on their promises.

The Right Accountant Is a Business Ally

Choosing an accountant isn’t just about crunching numbers. It’s about finding someone who understands your goals, simplifies your life, and helps your business thrive.

The right accountant helps you:

  • Stay out of compliance trouble
  • Avoid expensive surprises
  • Make sense of your financial picture
  • Helps you get a preview of your situation

If your current accountant isn’t checking those boxes, it might be time to look elsewhere. And when you do, ask these questions. Don’t settle for less than an accountant who treats your business like their own.

If you're ready to find an accountant who will support you year-round, communicate clearly, and help your business grow, reach out to us at TMA Accounting. We're happy to answer all these questions—and any others you have. Let's simplify your business together.