Imagine planning a big trip, but instead of packing your own bags, you have to trust someone else to do it for you.
It’s a little nerve-wracking, right? You’d want to make sure they know exactly what you need—because forgetting even one small thing could mess up the whole trip.
Now, think about your business. The stakes are even higher. Choosing the right accountant and bookkeeper is just like that trip. You’re trusting someone else with your financial details, and if they miss something important, it could put your business at risk.
Being a small business owner can get pretty overwhelming sometimes. Even if you’ve got a great team, there are always a hundred tasks that seem to be just one step away from spiraling out of control—especially when you’re in the early stages and wearing multiple hats.
When everything starts feeling like too much, it’s a sign you need some help. Step one is knowing when to bring in outside support. Outsourcing can save you time, money, and give you peace of mind. At some point, doing it all yourself just doesn’t make sense, so figuring out when to ask for help will keep things on track.
This article is Step 2—how to actually find the right help.
To help you find that perfect fit, here are seven questions to ask when you’re evaluating accountants and bookkeepers for your small business.
1. How Long Have You Been in Business?
The length of time a firm has been in business can be a strong indicator of its experience and reliability.
You don't want to be the training ground for someone who has no previous experience.
Look for specific examples of how they’ve helped businesses similar to yours or ask them for client testimonials.
2. What Certifications/Registrations Do You Have?
Certifications show that an accountant or bookkeeper is not just experienced but also committed to doing things right. They’ve put in the work to stay sharp and up-to-date in their field, and that’s the kind of dedication you want on your side.
3. How Will My Information Be Secured?
Your financial information is sensitive, and protecting it is non-negotiable. You wouldn’t hand over something valuable to someone who can’t keep it safe, and the same goes for your business’s financial data.
Make sure the accountant or bookkeeper you choose takes security seriously. Here are some important questions to ask:
- How do you physically secure your offices and servers?
- Are all of your sites encrypted?
- How is your network secured?
These details matter because strong security practices mean you can trust that your financial information is in safe hands.
4. How Well Can I Expect You to Communicate with Me?
If you’re trying to reach your accountant or bookkeeper with an important question and keep hitting voicemail, it’s natural to feel concerned.
You want someone who’s available when you need them. If there’s a problem with your finances, you should expect them to inform you immediately—keeping you in the loop and preventing small issues from becoming big ones.
Your financial partner should provide concise updates that respect your time and be flexible enough to connect with you in the way that works best for you, whether that’s by phone, email, or whatever you prefer. This way, you can always feel confident that your finances are being handled with the attention they deserve.
5. Who Will Actually Be Doing the Work?
It’s important to know whether a single individual will handle all of your needs or if the work will be assigned to a variety of people on a team.
A dedicated accountant can offer consistency and a deep understanding of your business, while a team might provide a broader range of expertise.
You should also ask whether all the work is done in-house or if they subcontract to offshore freelancers when their own workload gets too heavy.
6. What Kind of Reports Can I Expect to Receive?
A good accounting/bookkeeping firm should easily provide you with essential financial reports, including:
- Cash Position: A snapshot of your cash flow, with receipts and payments.
- Bank Statements: Detailed records of your checking, savings, and credit card accounts.
- Income Statements: A clear breakdown of revenue, expenses, and profit & loss.
- Balance Sheet: An overview of your assets and liabilities.
- Payroll Expenses: Comprehensive details on payroll costs.
Decisions you face related to your particular business may require other specific reports. Be sure your accounting firm is willing and able to provide them.
It should never be a hassle to get the information you need!
7. What Happens to My Files When You Are Finished with Them?
It’s important to understand how your financial files will be handled after the work is done. These questions will help you find out if your information will be managed securely and appropriately.
- Where will my files be stored? Are they stored online? In the offices? If so, for how long?
- Will I get my files back? When and how will they be returned?
- What happens to my files afterward? Are they destroyed after you send me copies?
- If we part ways, what happens to my files? How will they be transferred or disposed of?
Understanding these details keeps your peace of mind intact, knowing your financial records won’t end up in the wrong hands or mysteriously vanish.
Don’t Be Afraid To Walk Away If Something Doesn’t Feel Right
This is your business’s financial health we’re talking about—not a casual fling. Choose wisely, and you’ll have a financial partner who’s got your back for the long haul.
These seven questions are by no means the only ones you should ask an accounting/bookkeeping firm before you outsource your small business finances. You probably want to know how much it's going to cost you.
Learn more about what monthly accounting services can do for you—and what it might cost in "How Much Does Outsourced Accounting Cost?"
