Your Money, Your Rules | Money Mindset, Money Management, Abundance Mindset, Budgeting, Spirituality

154 | QuickBooks Got You Stressed? The Key Questions Every Woman Entrepreneur Should Ask a Bookkeeper

• Erin Gray | Wealth Coach, Former CFP and CFO

Share episode

Work with Me: (https://tidycal.com/eringray/45-min-call-with-erin)


Hiring a bookkeeper shouldn’t feel like handing your finances to a stranger and hoping for the best. In this episode, I walk through what it really means to find the right bookkeeper for YOU.  You want someone who understands your business, speaks QuickBooks fluently, helps you make confident money decisions and someone who you can connect with and enjoy working with.

You’ll learn the exact questions to ask before hiring, what to look for in both an energetic and technical fit, and how to set up clear monthly workflows that actually support you. I also talk about security, CPA collaboration, and how to create a financial partnership that feels grounded, transparent, and aligned with your growth.


Want to learn more or connect with me?


Step 1: Join my Facebook Community.

➡️ Join here

Step 2: Grab your free Human Design chart

➡️ Get your chart here

Step 3: Work with Me

➡️ Schedule your free clarity call here


From my soul to yours,

Erin

Erin Gray:

Today on the podcast, I am going to be sharing with you the questions that I would be asking if I was on a call with you when hiring your either first bookkeeper or if you're switching to someone else. So I'm going to share with you all of my thoughts on bookkeepers, hiring one, and also the questions that you need to be asking. So let's dive in. Okay, so as some of you already know, if you've been here a while, you know my history of working in my family's construction business for over 10 years. And so the depth and breadth of knowledge that I have in QuickBooks is immense to put it very lightly. I am very well versed in QuickBooks desktop, I should say, because when at my family's construction business, we did uh, I think it was called contractors edition, but it was a very robust system. Like if you have QuickBooks Desktop, which a lot of us don't anymore, that you know, we've a lot of us have moved to QuickBooks Online, but if you have just QuickBooks Desktop, I am 100% able to like, I could walk you through things by me just being on the phone with you, not even looking at the screen because I just know it so well. And I say that to say that I can only imagine the overwhelm that you might actually feel when trying to sit down and look at your books or talk to a bookkeeper or even your CPA. Because first and foremost, you're trying to, you know, understand the language of QuickBooks. Like it is, it is a language. Two, you're trying to understand accounting, which let's just be honest. I mean, I took accounting in a bunch of finance classes in college and you know, throughout my life. And it's not necessarily language that is like very uh supportive to learning, you know, it's like they they use different words for the same thing, like income and revenue. It's all the same. Like, why can't we just make it so simple and not make it complex? That's another topic for another day. So, you know, you've got your language of QuickBooks, you have the language of accounting, and then you also have just, you know, trying to understand how to read reports. So I just want to say, like, you are doing it, you are like take go easy on yourself because this isn't something that is taught, and we're kind of having to learn this and also run a business. So give yourself some grace. So before I get into the questions that I would be asking if I was on a call with you, or the questions that I would recommend if you were my client to be asking a bookkeeper, first and foremost, with anything, I always start from in the energetic piece. Like you have to like who you work with. The other day I was actually calling for um, because my husband is um starting a tree business. And so I was calling different insurance agents. And I was on the phone with this one lady and I could just feel my body tense up. And my husband was sitting right next to me because he's learning that back in process. And I had to take a breath and pause and be like, hang on a second, do you even energetically match this woman? And I got a no. And I'm like, okay, done. We're not even gonna go, like, I need to find somebody else. So I would encourage you to interview two to three people first and foremost, and see how you feel in your body and energetically when you work with them. Because these are going to be people that I always like, I advise my clients, these are people that you are going to work with for an extended, a long period of time. Like ideally, you want to work with them and grow and scale with them and years and years, right? Down the road. Now, things happen and you know, people change, but you know, careers or whatever it might be, but like really, it's not just somebody who's just going to like, you're gonna give them numbers and they're gonna put the numbers in and they're gonna just spit them back out at you. Like it's more than that. It is a relationship. I think it's an intimate relationship with not just your bookkeeper, but anybody that you hire. So, first and foremost, be thinking about what is, how do I feel when I'm with this person? Does this person seem like they like enjoy their job and have fun? Like there's been CPAs that I won't hire because they just feel like they just hate life, you know? So I don't want to be around somebody like that. Like I want somebody that likes their job, likes teaching me, likes to be, you know, supporting and serving clients. So that is first and foremost the question that I would ask you is like, do you actually enjoy being with this person, talking to them? Do you feel like that they would be a good mentor for you? Or do they you feel like they're just trying to, you know, check the box, get the get the reports out and and be done? So that would be my first and foremost like question I would ask you. Now, as we're going to dive into like the questions to ask your bookkeeper, I want to also back up and say here that it is extremely important that you actually know your books. And I know that that can feel like a lot when you're trying to grow your business, but I truly believe, and I've seen this with clients, if you don't take the time to sit down and understand your books, there's a couple of things that happen. Number one, you're gonna take yourself wherever you go and grow with your business. So if you don't understand your books now, what do you think, what makes you think you're gonna understand them when you're doing millions, 10 millions, 100 million in revenue? This is one of those foundational things that you need to sit down and take the time, even though your brain might tell you, uh, it's you know, it's taken away from XYZ. This is a foundational skill set that once you know this, then you can offload it to someone else and you can know what you are offloading. And you know, when someone quotes you prices, you know how long it takes, you know the value you're receiving or not receiving. And I think it's a really important skill set to have. You can learn from like there's so many YouTube videos. There's even like check like your local SBA. They even have like, I'm on my local in Boise, I'm on my SBA email list, and I see all the time that they have like QuickBooks classes. So you could do that. You could, you know, even pay, like this is what I did as I was learning. I was teaching myself a lot. And then I would pay the accountant. Now, accountants and bookkeepers typically don't mesh in terms of like they don't do the other person's job, but there would be questions that I would ask about numbers and I would just pay for an hour of her time to ask and dig deeper into the questions so I could understand it better. And I think that that type of investment that we spend to understand things at a deeper level is so important and valuable. So, with all of that said, let's dive into actually the questions that I would be asking if I was hiring a bookkeeper or I was on the phone with you, or you were my client and I was like, hey, these are the questions to ask the bookkeeper. First and foremost, what is their actual experience in working with your type of business? So I have clients that have online businesses, I have clients that have brick and mortar businesses. And those types of businesses, brick and mortar or online, are very types of, they're different types of businesses. So cash flow is different, profitability can be different. So it really matters that your bookkeeper is versed, number one, first and foremost, like in the industry that you are actually in. So if they are not used to working with your industry, how can they advise you and like project things that might be coming up for you and mentor you if they don't have any clients that are in the industry that you're in? So I would ask first and foremost, what experience do you have working with businesses like mine? The second question that I would ask is most bookkeepers typically use QuickBooks because a lot of accountants like to use QuickBooks, but just obviously verify that that is what they use and also ask them like, what is their workflow? So, meaning, like, are they going to retrieve online statements for you and then they're gonna reconcile all of your accounts? Or is it your responsibility to send them the statements and then they are the ones that true it up? So, really just asking them what is an actual month look like of us working together so you get an idea of what you can expect with working with them. And also then you can ask more clarifying questions if it's not maybe you want more support than that. So maybe even though you may not have a whole lot of maybe say transactions to do or accounts to reconcile, if you're wanting more support or you're wanting to be handheld a little bit more, maybe you actually need to pay for more time with them. So just really asking about like what is their workflow, what do they expect from you as a client? And what do you expect from them as a bookkeeper? The third thing that I would also ask is a lot of us, whether you're online or you are brick and mortar, a lot of us use like a payment processor, right? Like I use Stripe as my payment processor. I used to use QuickBooks when they allowed with desktop. Some people use other types of payment processors. So if your bookkeeper that you're interviewing isn't familiar with that, okay, first and foremost, know that. And then if you really like them and they just don't know that, but they're willing to learn the payment processing, how are they actually going to like bring that into QuickBooks? Are they going to keep it separate? Because sometimes it actually makes sense to keep it separate because the way that QuickBooks works is it can like do double entries and sometimes it just gets really messy. Like on the one hand, QuickBooks is like a really robust system. And then at the same time, it's like, oh my gosh, who, who, who, who thought of this? Because there's so many things that sometimes QuickBooks, I'm like, what are you thinking? But so if they're gonna keep it separate and they're not gonna bring it in, are they actually going to then itemize your income for you? So if your payment processor, let's just use me for example. Currently I coach one-on-one. But if I were to be coaching a group and my one-on-one clients, and let's say I also had paid workshops or I um had retreats or something like that, like I personally would want to know income in each of those areas so I could see what is my profitability in each of those things. So the same goes for you. So you want to be able to see along with your income and your expenses, so you can pull reports to actually see like what is profitable. Because if you're continuing to do a service that isn't profitable, then that's a that's information and data that you need to make a decision. Now, I always say go with your gut. And also, like if you don't know, you don't know and you can't like actually make informed decisions. So, how are they actually going to enter the data for you for your payment processor? Because so many of us use credit cards. And so are they gonna, you know, break all of that down for you, or are they just gonna bring it in and lump some, just like income? And if they are gonna just do income, I would advise you to push back and be like, I want to be able to see my individual income. Cause here's the thing I think about too, is you're not just setting it up for right now. Like you have to think about you as the business owner three, five, 10 years from now. And that's who you need to be acting from and interviewing from. So, you know, if you have a bookkeeper who's like, oh, well, we'll just, you know, cross that bridge when we get there. No, I actually want to set it up correctly now so that I grow with it and I can see. So be really clear on that. Um, are they going to break it down for you? Are they going to break costs down for you? Things of that sort. The third, or maybe the fourth question, you know, how often are you going to be able to communicate? What I've seen with some, how do I say this? Lower investment um prices, like with working with book, like the entry-level bookkeeping that's you might be doing with someone is they they aren't reconciled a lot of accounts, like maybe two or three, and they typically don't get on the phone with you, which I get it. Like you pay for their time and their knowledge, but just be aware of that. Like, what does your package, a lot of them do packages? What does your package include? Because if you are, you know, just have several, like two or three, maybe four accounts to reconcile, but you want to be able to talk to them once a month and they're like, Well, I don't talk once a month, you know, like I just send you your reports in an email, then that might not be the fit that you want, or you just might have to be to decide to choose to pay a little bit more with them in order to get a phone call or a Zoom call or something like that. So some bookkeepers do monthly reports, others offer weekly updates. Again, this is based on like probably the revenue of your business, the complexity of your business. And when I say complexity, what I mean is like the number of accounts and transactions and things to reconcile. So this goes back to like the pricing of the service and you know, what is their kind of they they typically have like three or four packages. So, really, you know, being clear on what are they going to here? We go back to expectations. What are you expecting from them and what are they expecting from you? And does that actually align? So if you're wanting someone to be on the phone, then you need to state that up front and you know, either pay for that extra or find somebody that will do that for you. Other things that I would think about is are they gonna file sales tax for you if you do sales tax? Do they true up what I mean when I say true up with your loan agreements? Is are they going to wait until the end of the year to itemize or categorize, you know, your principal and your interest if you have a loan? Or are they gonna do that on a monthly basis so you can see a true, you know, standing of where you are? Like I always in my family's construction business, anytime we had a loan agreement, I always did that monthly because I wanted to know, and it also saves a lot of time on the back end because you don't have to do journal entries. You know, I always liked to see where we are with our actual loan agreements or loan payments and what was our principal and what have we paid to interest. So, same thing goes for credit card reconciliation. So it's just important to ask them how many accounts are being reconciled in the level of service that they are actually providing. Okay, so number four, I would, and a lot of times they have like it written either on their website or um if they give you a scope of work, it's there. But like what's actually included in your services and what would be an additional cost? So, like I said before, some bookkeepers, you know, track your income and your expenses while others might be helping you do, you know, invoicing or payroll, or they work with the CPA to do tax prep. So just make sure that you know what is covered so that you're not, you know, getting towards the end of the year and you're, you know, you're three months in and you're like, oh, they don't do this? Uh okay, so what's that? So just be really clear. Also, a lot of them use what they call a portal. The same thing goes for CPAs. It's a typically most of the time, it is a secure portal, but you want to ask that question is it a secure portal? And is that how they communicate with you? And that's where you can upload your documents. Like, you do not want to be sending your documents with your Gmail or your, you know, work email. Like, I don't ever send anything that has social security or just anything. Like if they're a bookkeeper or they're a CPA, they need to have a portal. You need to be able, it needs to be secure and you need to be able to have your own login and you need to be able to upload it, period. Full stop. So also asking them, you know, with communication, like, do they prefer email? Can you call them at all? Is there an additional cost? So just ask, like what I say is I ask all the questions. And what I tell my clients is I always like to, when I'm interviewing someone, I will tell them, like, I will pay you for your hour of time. I don't expect you to just have endless consultations for free. But I want to be able to have an hour with you to ask my questions so that I can get them all answered versus feeling rushed to make a decision. And then I'm already in an agreement with you, and then I find out I don't really like, you know, your services or the way you're speaking to me or something like that. So I always advise clients like it is worth every single penny that you would pay an attorney for a consultation if they charge for a CPA and or a bookkeeper and insurance agents. But I mean, I would just anybody that is gonna be helping you with your business, I always start that off. Like, hey, would love to have a consultation with you, be happy to pay for you. I mean, even people I've had in my business, like with um video editing or people that I've, you know, were gonna help me with some website stuff. Like, I'll be happy to pay you for, you know, the time that we're gonna spend on the call just so I can ask my questions. And I think it's money really well spent because then you get to see and you get to really get your answers clarified and it's well worth the investment. Okay, so number five is do they actually work with your CPA and do they talk with them? Or are you expected to be the middleman between both of them? So I have yet to meet a CPA that actually knows bookkeeping. And so and that's not really their job, really, right? Like they they really are for the taxes and the planning. So I get that. But if you do not have a bookkeeper who is talking to your CPA and who you are talking to all three of them, or all three of you are talking, then I think sometimes things get lost in translation, or someone thinks somebody else is doing it versus like I had a client and I asked her about closing out year end. And I was like, Well, how did your CPA do that if your bookkeeper told you that it wasn't closed out? And she was like, Well, I don't know. And then she goes back and asks the CPA, and the CPA is like, Well, I just assumed that it was closed out. No, not an okay answer for me. You know, I told my client, I'm like, absolutely not. Like, we need to come back to your CPA and your bookkeeper and be like, okay, let's draw some, you know, expectations here because do not assume anything. You need to ask me questions. So maybe that's because CPAs don't want to ask the questions. Maybe it's because they don't want to feel like they have to ask and then they're gonna charge you for it. I don't know what it is. But like I'm always up front, very upfront with all of the people I work with and very clear on expectations because don't assume. Like, I don't want to work with anybody that just assumes, do not assume. Making sure that your CPA and your bookkeeper are talking to each other and that, you know, this is more so CPA of like doing tax planning. But with your bookkeeper, like there's a there's a place in QuickBooks where it says ask the accountant. And I have seen some bookkeepers, if they don't know, they'll just file it, they'll categorize it under there instead of picking up the phone or sending you an email and being like, hey, what is this charge? Where does it need to go? So then at year end, you have all of these questions for ask my accountant when these are things that could have been done and taken care of all along the year. So just be really clear like, what is your relationship like with either CPAs that you work with if you're looking for a new CPA, or I have a CPA already? What is your, you know, feelings and thoughts on working with my CPA and working closely, like on a quarterly basis, so we can make sure we are, you know, knowing where we are versus the end of the year. Okay. And then the last one I would say is how do you ensure accuracy? And like we already kind of talked about this, is like securing the financial data, right? So they're taking care of your financial information, it's sensitive information. So QuickBooks, like, what is their system to, you know, we already talked about the portal, but like QuickBooks, who else has access? Like sometimes bookkeepers will have other bookkeepers that work for them. So the person that you're talking to, and this goes for CPAs too. So this is a bonus for you. Whether you're interviewing your bookkeeper or your CPA, the question that you need to ask is Am I gonna be talking to you when it comes time for my books and for my taxes? Because sometimes the question is no, or excuse me, the answer is no. Actually, you're gonna be working with my, you know, newbie CPA that I just hired on, which I've had that conversation before as well. That's not a problem, but I'm not gonna pay your 25-year rate of you CPA when I'm teaching and training your new CPA. And also, I'm not gonna be spending time teaching and training above and beyond what just simple answers are, because let's just be honest, that's kind of your job. So, really being very crystal clear of like, hey, are you gonna be the one doing my books? Or am are you the face of the company and you have somebody else, which is not a problem, right? Like, yay for them for scaling, but also like, how is all of this protected? Who all has access to this? How does all of this work? Okay. And then a bonus one for you is, you know, who, if you go on vacation, who do I get to call? And some of them might say, Well, I don't go on vacation, you know, during the busy times. That's not the answer I'm looking for. Like, what is your protocol? Period. Like, tell me. Like, do I don't expect you to answer my calls on vacation? And let's just be honest, bookkeeping, it there's not really that much. Like, you know, with bookkeeping, there's not a lot of things that like have to happen right now. But like if they go out of town during, let's just say, typically they wouldn't, but let's just say that they were going out of town during like submitting your sales tax, or you know, when you go on when you do payroll. I don't know. It's just really being clear, like, what is their backup for you? Because everybody deserves to go on vacation. Everybody deserves to take time off. And you also deserve to be able to have someone support you while someone else is on vacation. Okay, that felt like a lot. I know. So go back, listen to this episode multiple times. Take your pen and your piece of paper and write down all the questions. As you know, if you ever need support, want support and mentorship along this lovely journey called entrepreneurship and life, I would be happy to support you. Just fill out the or click on the link in the show notes and you can schedule a time that we can talk. So, to recap, you know, what experiences do you have working with businesses like mine? What software are you using? Are they understanding your type of payment processor? How are you willing to communicate? What is included in your services? And two more. How do you ensure the accuracy and security of my financial data, along with what are you going to do when you go on vacation? Okay, it's always a pleasure. I'm rooting for you. Every single one of you have every single thing within you already. You are already highly successful, you are already highly prosperous and wealthy. And I think a lot of us just need to actually believe it. So until next time, I'll see you in the next episode.