Is there really a best and worst time to hire an accountant, a bookkeeper, or a financial strategist for your business? Yes — there are always better and worse moments to bring help onto your team.
The short version: you should have an accountant and a bookkeeper in your back pocket from the very beginning. They help you grow faster and analyze your business more deeply than you might think possible. Here’s how to time each hire.
The worst time to hire an accountant
The absolute worst time is tax season. Accountants are buried in existing client work from roughly February through April and rarely take on new clients then. You might find someone you’d like to work with, but getting in the door won’t be easy — they’re slammed.
Tax season is only a few months, but your business runs all year, and there are 365 days of records to compress into one form the government can understand. That’s why accountants work overtime during those months, making sure their clients’ data is accurate. And if you’re scrambling to hire during tax time, you’ve done some poor planning — you won’t get the chance to find someone you truly connect with and who understands your business.
One more obstacle: with so many businesses moving online, plenty of accountants still haven’t fully adapted to understanding online businesses and how their finances work. You need someone in your corner who gets online business — and specifically your business, since no two are the same — and can classify your transactions correctly.
The best time to hire an accountant
The simple answer is any time outside tax season. But the answer you really need to hear is when you first start your business.
Financial questions will come up, and you’ll want someone to ask. If you also have a bookkeeper working with you regularly, you may only need to talk to your accountant quarterly or annually — but the point is they’re on your team and there for you. Hiring early also gives you time to meet with a few potential accountants, get a feel for their energy and how they work, and confirm they understand online business before you commit.
The worst time to hire a bookkeeper
The worst time is when you need a year’s worth of records prepared for taxes in little to no time — for example, it’s already March and you need to see what last year looked like — or basically any time you want a rush job. Bookkeepers can work some magic, but sorting and analyzing a year of data overnight isn’t possible. And the faster you want it done, the more you’ll pay.
The best time to hire a bookkeeper
Again — right from the start of your business. You don’t want to know how many clients have come to me with years (plural) of bookkeeping that needs to be done. They didn’t know how to do it, were afraid to hire someone, and kept going without help — until a letter arrived from the IRS saying they owed money or hadn’t filed. And they couldn’t file, because they had no idea what their accounts even looked like.
Save yourself the time, hassle, and stress and hire a bookkeeper early. As with an accountant, do your research, find someone whose vibe and energy fit, and make sure they understand your business. Also make sure your bookkeeper has an actual education in accounting — not just someone who decided they were good with numbers.
What about a financial strategist?
A financial strategist has an accounting and financial background and helps you dig into your money even more deeply. To really benefit from one, you first need a bookkeeper so your finances are already sorted and organized. Once everything’s in order, a strategist can take your numbers and help you analyze them further so you can scale faster.
The best time to hire a financial strategist is after you’ve been in business at least a year and have a year’s worth of organized data. The worst time is before you’re making a decent amount of money, because there aren’t enough patterns yet to help you scale.
The bottom line on timing your financial team
There genuinely are best and worst times to hire accountants, bookkeepers, and financial strategists. You should have an accountant and a bookkeeper in your corner from the beginning — even if you think you can’t afford them. Because if you think you can’t afford them now, wait until you get an audit letter: then you really won’t be able to afford them, but you also won’t be able to go without.
When you do hire, interview your candidates so you understand who they are, how they can help, and whether their energy fits. And once you’ve been in business a year or more, add a financial strategist to help you scale. So tell me — do you have an accountant, a bookkeeper, and a financial strategist on your team yet? When are you going to bring them on?
This article is for general educational purposes only and is not legal, accounting, or tax advice. Always consult a qualified professional about your specific situation.