11 Questions to Ask Before Hiring an Accountant

 Table of Contents The Day I Fired Myself It was 1 a.m. on a Tuesday in April. My online boutique had just had its best quarter ever, but I wasn’t celebrating. Instead, I was surrounded by a sea of crumpled receipts, staring at a spreadsheet that looked more like abstract art than a financial statement. I was trying to figure out if I could depreciate my new shipping label printer. I remember thinking, “I spent four years building this brand I love, and now I’m losing sleep over a printer.”  That was the night I fired myself… from being my own accountant.  For so many freelancers and small business owners in the USA, this story is familiar. We start out wearing all the hats: CEO, marketer, customer service rep, and, yes, bookkeeper. But there comes a point where the time and stress of managing the finances cost more than the money you think you’re saving. The Federation of Small Businesses revealed that small business owners spend up to 44 hours per year on tax compliance alone. That’s a full work week you could be spending on generating sales, creating your product, or just recharging.  Hiring an accountant isn’t admitting defeat; it’s making a strategic investment in your success and sanity. But how do you find the right person? It’s not just about finding someone who can file your taxes. It’s about finding a financial partner.  To help you find that partner, here are 11 essential questions to ask your potential candidates.  11 Questions to Ask Before Hiring an Accountant 1. Do you have experience with other businesses like mine?  The financial landscape of a freelance graphic designer is vastly different from that of a small e-commerce shop or a local restaurant. An accountant who specializes in your field will already be familiar with the specific deductions, tax challenges, and revenue models unique to your industry. They won’t be learning on your dime. Ask them to give examples of how they’ve helped similar businesses.  2. What are your credentials (e.g., CPA, EA)?  These letters represent very different skill sets.  Knowing their designation tells you exactly where their expertise lies.  3. Who will be my main point of contact?  At larger firms, you might meet with a senior partner initially, but your day-to-day work could be handled by a junior associate. There’s nothing wrong with this model, but you need to know who you’ll be speaking with regularly. Building a relationship with the person who is actually in your books is crucial for trust and clear communication.  4. How do you structure your fees?  Why it Matters: There’s no single answer here, so you need to find what works for you. Common structures include:  A retainer model is often preferred by business owners who want predictable costs and ongoing access to advice without worrying about getting a surprise bill for every phone call.  5. What specific services are included in your fee?  This is arguably the most important question to avoid future misunderstandings. Does their fee include just the annual tax return? Or does it also cover quarterly estimated tax calculations, bookkeeping cleanup, payroll processing, and responding to tax notices? Get a detailed list. You need to be comparing apples to apples when you evaluate different accountants.  6. What accounting software do you prefer to work with?  The days of the shoebox of receipts are over. Modern accounting live in cloud tools such as QuickBooks, Xero, Wave, or Fynlo. You need an accountant who is proficient with your current system or can seamlessly migrate you to a better one. Their comfort with technology is a good indicator of their overall efficiency.  7. Are you available for questions throughout the year?  Your business doesn’t just happen during tax season. You might have a question about a major purchase in June or need to make a hiring decision in October. You want an accountant who sees themselves as a year-round advisor, not just a once-a-year tax preparer. Their answer will tell you a lot about their service philosophy.  8. How would you describe your approach: are you focused on historical compliance or proactive planning?  A good accountant keeps you compliant and makes sure your taxes are filed correctly. A great accountant looks ahead. They’ll come to you with ideas for tax savings, help you plan for future growth, and advise on strategies to improve your cash flow. You’re looking for a proactive partner, not a financial historian.  9. Can you represent me in the event of an IRS audit?  While IRS audit rates for small businesses are relatively low, they are not zero. If you are ever audited, it can be an incredibly stressful and time-consuming process. CPAs and EAs have unlimited representation rights, meaning they can represent you before the IRS on any matter. Knowing you have an expert in your corner provides invaluable peace of mind.  10. From your experience, what is the biggest financial mistake you see business owners in my position make?  This question gives you a glimpse into their expertise and proactive mindset. Their answer will reveal how well they understand the common pitfalls of your industry. It also opens the door for them to provide immediate value and show you how they can prevent you from making those same mistakes.  11. What information do you need from me to get started?  A professional accountant will have a clear, organized onboarding process. Their answer to this question will demonstrate their level of organization and set clear expectations for the working relationship. It shows they have a system and are ready to get to work.  Finding Your Perfect Match Choosing your accountant isn’t just ticking boxes, it’s about forging a trusted partnership. Take the time to shortlist candidates, interview them, compare answers side by side, and go with the professional you trust.  At Fynlo, we understand the challenges of financial management firsthand. That’s why we pair you with seasoned professionals who speak your language. Our junior accountants bring over five years of experience, while our senior accountants boast

Why Bookkeeping Isn’t Just for Big Companies

I still remember the first time I called myself a “business owner.” I’d just launched my Etsy shop selling handmade candles, and I felt unstoppable—until tax season hit. My “bookkeeping” was a pile of crumpled receipts in a desk drawer and a bank account I checked with one eye closed, hoping I hadn’t overspent. When I realized I’d missed $900 in deductions and owed an extra $400 because I hadn’t tracked my expenses, I felt crushed at my desk. That moment taught me something I wish I’d known sooner: bookkeeping isn’t just for corporate giants with skyscraper offices. It’s for freelancers, side hustlers, and small business owners like me—and you.   If you’re a freelancer designing websites or running a small bakery, you might think bookkeeping is too complex or unnecessary for your one-person show. But it’s not about being “big”—it’s about taking control of your finances. The hard truth is, neglecting your books is one of the quickest ways to watch your dream crumble. It’s not about becoming a math whiz overnight; it’s about understanding the financial heartbeat of your business. And for the 75 million freelancers in the U.S., and the millions more small business owners, that heartbeat can be the difference between thriving and just surviving.  Table of Contents The Sobering Numbers Behind the Dream We all love a good success story, but it’s crucial to acknowledge the reality. According to the Bureau of Labor Statistics, about 20% of new businesses fail within the first two years. Dig a little deeper, and a staggering 82% of small business failures are due to poor cash flow management, as reported by SCORE. Think about that. It’s not necessarily a bad product or a lack of passion that sinks the ship. It’s running out of money. It’s not knowing where your money is going, who owes you, or when your next big expense is due. That’s where bookkeeping makes its quiet, heroic entrance. 5 Ways Bookkeeping Empowers Freelancers and Small Businesses 1. Slash Your Tax Bill (Legally) Detailed expense tracking turns everyday costs into legit write-offs. By assigning each transaction to categories like office rent, utilities, software subscriptions, professional fees, and business mileage, you ensure nothing slips through the cracks. Many pass-through businesses qualify for the Qualified Business Income deduction, shaving up to 20% off taxable income. For instance, on $100,000 net profit, that’s a $20,000 deduction—potentially reducing your federal tax liability by around $5,000 at a 25% bracket . Add retirement-plan contributions (up to $23,000 for a Solo 401(k)) and self-employed health-insurance premiums, and you can stack multiple tax-saving strategies—all made simple when your books are up to date.  2. Stop Cash-Flow Surprises Profit on paper doesn’t always equal cash in the bank. This distinction is critical: a business might show a profit, but if customers aren’t paying their invoices promptly, cash flow can still be a major problem. In fact, 46% of small businesses seeking financing did so just to smooth out cash-flow bumps. To stay ahead of shortfalls, carve out a weekly bookkeeping slot and:  By making these three steps routine, you catch cash leaks before they become full-blown crises—and keep your bank balance as healthy as your bottom line.  3. Make Choices That Grow Your Business Real-time dashboards turn raw numbers into actionable insights. With up-to-the-minute profit-and-loss, balance-sheet, and cash-flow reports, you can: Don’t just take our word for it—here’s what the numbers say. According to a 2024 QuickBooks survey, 95% of growing small businesses say integrated, automated accounting systems are critical to scale, yet the same percentage struggle with manual data entry. Clean books eliminate guesswork, so you invest with confidence.  4. Get Ready for Loans or Investors Opportunities to expand—or the need for capital to tackle unexpected challenges—can arise at any moment. When they do, financial readiness is non-negotiable. Banks, agencies such as the U.S. Small Business Administration (SBA), and potential investors will ask for clear, accurate statements to assess your risk and viability. Keep these documents up to date and on hand:  Lenders and investors often make decisions within days; messy or incomplete records can stall or even derail your application. By maintaining clean books, you shorten approval timelines, minimize follow-up questions, and enter negotiations from a position of strength.  5. Reduce Financial Uncertainty and Stress Messy finances weigh you down. Uncertainty about your cash position and looming deadlines fuels anxiety. In fact, 49% of small-business owners report their mental health has suffered from the stress of managing their finances.  The good news? You don’t need hours of work to turn that around. By carving out just 15 minutes each week to update your books—assigning transactions to the right categories, reconciling recent bank activity, and glancing at a one-page financial dashboard—you’ll eliminate nasty surprises from unexpected tax bills or overdrafts. Over time, this simple, predictable habit builds genuine confidence in your money management, frees up mental bandwidth to focus on your clients and creativity, and replaces financial dread with clear, calm control.  “The journey of a freelancer or a small business owner is one of passion, grit, and a whole lot of heart. Don’t let the fear of numbers hold you back from building the thriving business you deserve. Replace the shoebox approach with organized records and gain the clarity and confidence that come from a clear view of your finances. Your future self will thank you for it.”  Getting Started It’s easier than you think. You don’t need to be a certified public accountant to get your books in order. Here are a few simple steps to get you started:  > Schedule your free discovery call < Further Reading Continue your learning journey with these related resources: