Hiring a Bookkeeper


"Should I hire a bookkeeper?" is an incredibly common question early-stage business owners ask. 

I'm generally always a yes on this. If business owners wanted to be bookkeepers, they would have gone into the bookkeeping business. Adding a bookkeeper to the team is a long-term investment that enables growth of the business and improved quality of life for most owners. Business owners have two kinds of companies - growth-focused businesses or lifestyle businesses. Both benefit from professional accounting/bookkeeping support. A few key points:

  • The bookkeeper has to be a professional who knows what they are doing. Too often, the first bookkeeping "hire" is the spouse, a friend, or maybe a bookkeeper who has been banging around town forever but doesn't really have proper accounting and software training. Perhaps they aren't familiar with the industry. When the first attempt to bring in help fails, the business owner gets gun-shy about trying again and holds onto these tasks. Hiring a pro is critical.  

    • Look for a firm with expertise in your business type and region.

    • They should understand your software and not be learning on your time.

    • Look for a firm with solid systems including redundancies and documentation so that if, and when, they have staff turnover, you aren't starting from scratch. You can ask questions like what happens when your bookkeeper goes on vacation or is out sick. Is there more than one person prepared to work on your account? How do they document client work and workflow?

    • Are they insured? Stuff happens.

    • What kind of background checks and screening do they do on their staff?

    • If you outgrow working with outsourced teams, can you hire the bookkeeper you have been working with in-house, and what does that cost?

    • Are they using overseas teams? (There is nothing wrong with this, but understand their data security protocols.)

    • What are their availability and communication standards? Do they text? Email only? Will they take a call, or is it electronic communication only?

    • What time zones will the people you work with be in? 

    • What are their data security measures?

    • Are they pricing by the hour or a fixed fee? Hint: you probably want a fixed cost for a defined scope of work.

    • Do they utilize AI in their practice, and does client information get input in any way to AI LLMs? - This is a question many firms aren't prepared to answer. While AI is a REALLY powerful tool, you probably want a firm that is at the cutting edge and keeping up with the possibilities but has a firm NO AI use-by-staff policy at this time.

  • Business owners must do the homework and build the skills to do their part. 

    • Can you read financial reports, or are you relying on poking around in your accounting software?

    • Build the vocabulary you need to communicate and collaborate with your accounting pro. If you are still working on that - be prepared to describe to your bookkeeper what you are trying to figure out and let them help you get the data needed. Too often, owners ask for specific reports and then get frustrated when it doesn't tell them what they want to know. 

    • Get into a routine. Don't be a chaos monster. Set a weekly, monthly, quarterly, and annual schedule for the accounting cycle. Know what your duties are. Do your part on time.

  • Checks and balances no matter how much you trust your team. Have systems that hold everyone accountable, prevent theft, and detect errors early. Follow best practices for theft prevention and audit readiness. 

  • Go REMOTE - Even if you are hiring someone in your local area, utilize cloud and digital tools. Remote accounting solutions will create flexibility for all (including you), allow for quick pivots when needed, be more secure, affordable, and have the most efficient options in the marketplace. 

Business people who hold onto bookkeeping responsibilities often find their ability to scale the business is limited because: 

  • So much of their time is consumed by bookkeeping and accounting tasks that they aren't able to excel in other aspects of the business, like sales, revenue growth, keeping up with industry trends, or other areas their core skills bring to the operation. 

  • Lack of accounting eduction and training can lead to costly errors or practices that don't serve the business long term.

  • They develop a false sense of security because they are "in the numbers" and forget to step back and do long-term financial planning and optimization.

If you are building a lifestyle business, this all applies as well. Outsourcing accounting tasks to qualified professionals will free you up for the lifestyle part of things. Get the time back and free up the headspace for creativity, family time, leisure activities, travel, and self-care. 

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