105 | 5 Essential Questions to Ask Before Hiring a Bookkeeper (and Avoid Costly Mistakes)

Ready to hire a bookkeeper but afraid of making the wrong choice? You’re not alone.  Finding someone who truly understands your business finances is critical—and rushing this decision often leads to expensive missteps.

In this episode, I dive into the 5 non-negotiable questions (plus one bonus!) you must ask before bringing a bookkeeper onto your financial team.

Whether you're hiring your first bookkeeper or considering a switch, these questions will help you:

✅ Avoid costly hiring mistakes
✅ Align your bookkeeper with your specific business needs
✅ Set clear expectations from the start

Here’s what we cover:

• Why industry-specific experience matters—especially for online businesses
• How to ensure software compatibility with your accountant
• The ideal communication rhythm and report cadence
• Why understanding your own finances (even a little) can protect you from major losses
• The importance of service boundaries, security protocols, and yes—vacation coverage

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From my soul to yours,

Erin

Transcript

Introduction to Essential Bookkeeper Questions

Erin Gray 0:00

On today's podcast, we're going to be talking about hiring a bookkeeper, specifically, the five essential questions I think you need to be asking before bringing someone onto your team. Whether you're hiring your first bookkeeper or you're looking to switch to someone new. These questions are going to help you be able to find the right fit for you. Do you want to create a system to stop avoiding your money? Maybe you're feeling guilt and shame when it comes to finances. Welcome to your Money, your Rules. I'm Erin, a former certified financial planner and CFO, and yet I used to avoid my money and had fear, no matter how much we had. I can't wait to teach you how I overcame my money avoidance and started consistently managing my finances in a really simple way. It's time to get comfortable with money. Before we dive into this week's episode, I want to invite you to join me for a one-on-one master your money coaching session. During this hour, we'll work together to create a tailored plan that helps you align your finances with your unique goals, energy and mindset. If you're ready to transform your relationship with money and create the freedom and abundance you deserve, head over to my website, generatealifewelllivedcom and schedule your session.

Why Understanding Accounting Software Matters

Erin Gray 1:11

So let's talk all things bookkeeper. To be completely transparent, I still do my own books. I learned the hard way with QuickBooks on what's called QuickBooks Enterprise. It's a desktop edition which is for construction, and it might be some of the toughest software to understand. And yet, because I always love to talk about how we learn through obstacles, I am so grateful that I learned on some of the hard stuff, because now I'm able to look at clients' reports in such a minimal amount of time, because I spent 10 years doing it in my family's construction business. I mean, I can only imagine the overwhelm that some of you might be feeling trying to learn the language of QuickBooks or trying to read reports, and so I want to dive into.

Erin Gray 2:00

You know a bookkeeper isn't just someone like that tracks your numbers to. You know a bookkeeper isn't just someone like that tracks your numbers. There's someone that you're going to trust with your financial data and someone who's going to help you. I view everyone on your team as someone that's helping you get to where you want to go, and so asking the right questions upfront, I think, is going to save you so many headaches later. And this might sound like I'm talking out of both sides of my ass, so bear with me here. On the one hand, I totally think that you should know how to do QuickBooks and how QuickBooks works, because the more you know, the better you're able to converse with your bookkeeper and your CPA Like you're speaking the same language're able to converse with your bookkeeper and your CPA Like you're speaking the same language as them. And then, on the flip side of that, I also get that it's like a foreign language and that spending time learning it can feel very overwhelming and cumbersome. So, for those of you that feel this way, I just want you to ponder taking some courses, watching some YouTube videos, asking your local you can even ask your local SBA community. They typically have classes at a lower cost that you can pay for Um, or you can even pay your bookkeeper for some upper level training.

Erin Gray 3:16

I know that when I was trying to understand in Texas, we have something that's called franchise tax, which is above and beyond federal taxes or state taxes, and when I came into the business, I thought when I started diving into franchise tax, I thought that we were totally overpaying which we were and so I really started diving in to it. I taught a lot of it myself, but then I would pay the CPA for advice or clarity or understanding or you know, to answer my questions so I could really start to understand how this works, so we could get a handle on it, and it ended up saving, like I don't know, 50 plus I don't know how much thousands of dollars. That I saved by understanding how it worked, because it wasn't being done, even though the CPA was doing the taxes for us right, like the data that we give them also matters, and so the way that the data was being presented wasn't done in the correct fashion. So I say that to say you can pay for advice in order to increase your you know, knowledge and expertise, because it's been my experience. What we don't know and then when we outsource, that can end up costing us more than we originally imagined in time and money. Because when we aren't aware of the time involved for that other person and they're just telling us it takes X, y, z time, but we haven't done it ourselves, how do we know that? That's true. So if a bookkeeper quotes you you know, I'm just using numbers $200 for additional reports, and you haven't ever pulled those reports before. You don't know if that number is high or low. Yes, you can ask your business besties and colleagues, but when you've done it yourself, you know the time involved, and I always want to say that. Make sure you understand that I am an advocate for paying for support. I'm not saying do it yourself, and I'm also saying you have to know things when you outsource them.

Five Key Questions to Ask Bookkeepers

Erin Gray 5:16

If you're unsure of what to ask when hiring a bookkeeper, here are, I think, the five really good questions to ask them. Number one what experience do you have working with businesses like mine? This is the same question that I talked about on the CPA podcast. Like what would you ask your CPA? Because every business is different and definitely, I believe, brick and mortar businesses are different than online businesses. So most of my clients have online businesses and I've noticed that most accounting software is more for brick and mortar businesses. So you want to make sure that your bookkeeper understands the online business space, because if they don't, they may be like, well, that can't be counted for, or why are you doing that? So you really want them to make sure that they work with online businesses. If you are an online business, every industry has different financial needs, so you want a bookkeeper who understands the specific challenges and cashflow patterns of your type of business. Number two is what software do they use and do they have experience with the one that you're using?

Erin Gray 6:20

If you already use QuickBooks I know Xero is another one or maybe another platform just make sure that they're familiar with it. I've seen some people use FreshBooks. I'm not familiar with that. Like I said, I grew up on. You know over the last what 15 years I've been using QuickBooks. I know it. I'm not gonna learn a different software system. Most accountants want and, like you know, quickbooks reports, so that's what I've decided to keep with. So just make sure that they're going to use the same one as your accountant. Or, if they don't ask your accountant, are you okay with that? Because the last thing that you want to do is have software that the bookkeeper uses and then the accountant might charge extra because the systems maybe isn't either easily transferable to them or they're not as familiar with it or looking at that. So I always ask the CPA like, what is the software program that they use? And most of the times it's QuickBooks. So just making sure and most bookkeepers use QuickBooks, but just making sure that you're kind of all on the same page.

Erin Gray 7:32

Number three is how often will we communicate and what reports are you going to provide? You know some bookkeepers do monthly reports. Some offer weekly updates. Some I have heard through the grapevine of other bookkeepers that I've worked with don't do monthly reports. And if that's someone that you're interviewing, I would say run, because at a minimum you want monthly reports so you can see where you are. Clarity comes with your numbers and in real time you know if you are pulling reports for three months ago, that's, that's long gone, right. So clarify what kind of insights you're going to get and how accessible that they will be. Are you going to get just a P and L and a balance sheet? Are you going to get an AR and AP report? What are the reports that they're willing to give so you have a clear picture of where you stand financially?

Erin Gray 8:23

Number four is what's included in your services and what would be an additional cost. Some bookkeepers only track expenses. Others will help with the invoicing, payroll If you're at that stage tax prep just making sure you know what's covered, so there are no surprises. You know, does the bookkeeper talk to your accountant for you or are you the go between? And I do think you need to be involved in both but like, what exactly is their role? So you're very crystal clear. Most bookkeepers already have. You know they have a contract. But like, what exactly is their role? So you're very crystal clear. Most bookkeepers already have. You know they have a contract, but just making sure that's very clearly spelt out when you hire someone.

Vacation Coverage and Business Continuity

Erin Gray 9:02

And then the fifth one is how do you ensure accuracy and security with your financial data? Your bookkeeper is going to have access to your sensitive financial information. So ask them how are they going to protect your data and what systems do they have in place to prevent errors? And I have a bonus one for you. Number six is how often do they go on vacation and who takes care of you when they're gone? So if they are someone who likes to travel a lot and they are out, what happens if you have questions? How are you going to get ahold of them? Do they have backup team members? Are they big enough where they kind of have a firm, or is it just a one man, you know, one woman show? Like, what is their process for when they aren't working?

Erin Gray 9:49

Okay, so to recap, six ones I would think about and ask what experience do they have working with businesses like yours and get them to start talking and just to share with you. That way you will be. I think through the sharing you'll be able to create more questions. Number two what software do they use, and do you have experience with the one that I use? Number three how often will they communicate and what way will they communicate? So if they only want to talk via email and they charge extra for phone, okay, what is that cost? And what reports are they going to provide on a monthly basis that are included in that fee? Number four is what is included in the services and what would be an additional cost? Five how do you ensure accuracy and security with financial data? And then my bonus one is if they go on vacation, who is their backup person? Who takes care of you when they're gone? What does that look like?

Final Thoughts and Community Invitation

Erin Gray 10:43

You know, having the correct bookkeeper for you can make managing your finances so much easier. Right, and hiring the wrong one can cause a lot of stress. I've had several bookkeepers friends that have gotten clients from other bookkeepers that said they were doing what they were supposed to do and they weren't. So just really be very clear, very make them be very transparent as to what you want what you expect, so that you don't find out the hard way, right With time and or money, that you're not getting what you paid for. So that's what I've got for you today.

Erin Gray 11:17

If you want more tips on managing your business finances with confidence, being with your money, having more fun with it, I would love for you to join my free Facebook community Money Mindset Tips for Women in Business. You can join with the link in the show notes or you can just go to Facebook and search Money Mindset Tips for Women in Business. Okay, thanks for being here. I'll see you in the next episode. Did you learn something today? Do you know another female entrepreneur who might be avoiding her money? Will you send this episode over to her for me and, if you have it in you, please leave me a review for this podcast. It helps the show grow and I love hearing from you. See you next week.