How to Set Your New Bookkeeper Up for Success — Whether In-House or Outsourced

Hiring a bookkeeper—whether as an employee or a contractor—can be a huge relief for any business owner. Delegating the financial tracking and reporting frees up your time and mental space to focus on running and growing your business. But hiring a bookkeeper is only the first step. Helping them succeed is the key to getting accurate books, timely insights, and peace of mind. 

Here are some essential tips to ensure your new bookkeeper is set up for success from day one—whether they’re sitting in your office or working remotely. 

Finding the Right Bookkeeper for Your Business 

Before you can help a bookkeeper succeed, you have to find the right one. Not every bookkeeper is a good fit for every business. Some specialize in certain industries, while others focus on businesses of a particular size or growth stage. Think carefully about what you need—do you want someone who just handles the basics, or someone who can provide insights and advice as your business grows? 

If you're considering an in-house hire, look for candidates with experience in your industry and proficiency with the accounting software you use. For outsourced bookkeepers or firms, ask about their onboarding process, communication standards, and how they ensure data security. Don’t be afraid to ask for references or case studies. A good bookkeeper should also ask you thoughtful questions to understand your needs, not just sell their services. 

Finding the right fit may take a bit of time, but it’s worth it. A strong bookkeeper relationship—whether on payroll or through a third-party firm—can be one of your most valuable business assets. 

1. Share Information Early and Often 

Your bookkeeper can’t do their job well if they don’t know what’s going on. From business goals to big purchases and even seemingly minor changes (like a new subscription service or payment method), it’s important to keep them in the loop. 

• Provide past financials or access to your current accounting system. 

• Share organizational charts, vendor lists, client payment terms, and any special procedures. 

• Explain your business model clearly. Not every business tracks revenue and expenses the same way, and context helps your bookkeeper categorize things correctly. 

2. Be Available—Especially Early On 

Even experienced bookkeepers need your input at the beginning. You know your business better than anyone, and they’ll have questions about your preferences, policies, and the history behind some transactions. 

• Set up regular check-ins at first—weekly or biweekly. 

• Respond promptly to their questions to avoid delays or mistakes. 

• Make it clear who they should reach out to for specific information (you, an office manager, or someone else). 

3. Give Access to the Right Tools 

A common mistake is forgetting to give the bookkeeper access to the software or accounts they need to do the job. This can slow everything down and cause frustration. 

• Grant access to your accounting software (like QuickBooks, Xero, or Zoho). 

• Give them view access to your bank accounts, credit cards, payroll systems, and POS platforms. 

• If you use shared drives or document management systems, make sure they’re invited to the correct folders. 

• If your bookkeeper is outsourced, set up secure access methods and clarify your firm’s privacy and data security expectations. 

4. Be Willing to Train 

Even if your bookkeeper knows accounting, they don’t know your business yet. Take the time to walk through your specific workflows, naming conventions, and systems. 

• Explain any custom reports or metrics you use. 

• Walk them through how you handle reimbursements, mileage, petty cash, or invoicing. 

• If you have industry-specific rules or reporting (like job costing in construction or 1099s for subcontractors), make sure to review those. 

Investing some time upfront will pay off in fewer errors and a faster ramp-up. 

5. Check In Regularly 

Don’t assume silence means everything’s running smoothly. Especially during the first few months, periodic check-ins can uncover miscommunications, highlight improvement opportunities, and strengthen the working relationship. 

• Ask what’s going well and what they need from you. 

• Review reports together to make sure they match your expectations. 

• Use these meetings to realign goals or adjust procedures if needed. 

Regular check-ins also help avoid a pileup of issues at year-end or during tax season. 

Final Thoughts 

Your bookkeeper can be a valuable partner in your business—someone who helps you spot trends, avoid costly mistakes, and stay compliant. But like any team member or contractor, they need support, communication, and access to the right tools. 

Whether in-house or outsourced, a successful bookkeeping relationship is built on mutual trust and good systems. Follow these steps to help your bookkeeper hit the ground running—and keep your business financially healthy. 

Contact us to connect with an experienced firm of bookkeepers here.