Bookkeeper tells ALL + 16 questions you gotta ask!

written by Bari Tessler January 24, 2013

Golden Nugget #4: Money Practices. 
Bookkeeping Love + Empowerment, Part 2 

Today we’re taking an even deeper cut into this burning money question:

Should I hire a bookkeeper, or do it myself?

(In case you missed it, here’s Part One on this topic, where we navigate through the choices, the dynamics, and the nuance of this big question.)

Happy drumroll + a few shoulder shimmies . . .

Jessica Reagan Salzman is joining The Art of Money as a Guest Teacher during the Money Practices phase of our program. She is a Bookkeeper Extraordinaire and the founder of Heart Based Bookkeeping. In addition to my teachings and guidance on crafting your own money practice (like a self-care practice) on a daily, weekly, monthly and yearly basis, Jess will be helping everyone choose the best bookkeeping system, or tracking tool for their needs. As a group, we will be reviewing roughly 6 systems to choose from. Jess will be a wonderful resource for The Art of Money community, and I’m so excited to have her here!

Q & A with Jess

Do you have advice/suggestions to give someone to help them decide if they are ready to hire a bookkeeper or do it themselves?

One of the absolute biggest factors in this question is “What’s your preference?” Do you as the business owner have a gut feeling as to whether or not you will ever be willing to do this new thing you haven’t done before? Some business owners run at the thought of doing business bookkeeping, but once they learn that the fear is simply an indicator of something unexpected, then they can dive in and learn how to do it for themselves. And in the grand scheme of things there are also people who just don’t want to spend their TIME doing the bookkeeping now, for whatever positive reason, and so they want to hand it off to a bookkeeper. There’s also every other imaginable scenario in between, but yes – asking within do I want to do this or have this done for me? is a great first step.

How does someone know if a bookkeeper is a good match? traits, qualities. what values to look for?

For me the most important factor I have found in working with my clients is a match of personality and approach. I think it’s incredibly important for a business owner to feel safe when it comes to working with a bookkeeper, and the connection that they feel to the person they decide to work with in this capacity should be one that lifts them up and allows them to feel much better about money and bookkeeping. A relationship with your bookkeeper built on trust will be a relationship that serves you well. It will allow the bookkeeping to provide insights and recommendations for improving money matters as well. Which for me is the ultimate reason to do bookkeeping in the first place.

What does having a bookkeeper look like? (what will the bookkeeper do?)

Bari, this is a great question! To answer this I must say that your teaching around learning to do the bookkeeping yourself first is a perfect complement to this question. Once you know and have been doing the bookkeeping yourself for a period of time, you will easily be able to decide if you want to continue or if you want to pass some or all tasks off. This is how you are able, as the business owner, to create your own response to this question! 😉 I have, over the years, learned how to specialize in creating a relationship with my bookkeeping clients that is as unique as they are. And I encourage every single conscious business owner to do the same for their relationship with whomever is working on their books. We have some clients that enter everything and have us review and provide advice & insights on a monthly basis. That’s one unique way of working with a bookkeeper. It may even be a little out-of-the-box. We also have clients that have us do almost all of the work, (data entering, reconciling, reporting) so there are both ends of the spectrum available for every single type of bookkeeping need out there. But overall I recommend designing a bookkeeping system with your bookkeeper that reflects who you are and is set up the way you want it to be. And if you aren’t even sure what the options of working with a bookkeeper look like in general, which is not at all uncommon, then connect with a few bookkeepers and trust your gut instinct and/or intuition as you begin exploring the connection.

What does doing own bookkeeping look like? (what will you do?)

It can vary depending on how you structure the system, but in most cases, monthly bookkeeping looks like sitting down to enter some numbers into your system, a system you’ve designed based on your bank accounts and credit card accounts and PayPal, and the list goes on and so forth. And there’s always the tasks of paying bills and making bank deposits that also make up a couple very important functions within the bookkeeping division of a company. I’m sure you haven’t forgotten about those, since most of us handle that stuff ourselves. For my clients it looks like sitting down to work with QuickBooks, entering and reconciling data, and then running reports that provide insight into the numbers side of the business. It can look like a great opportunity on a monthly basis to really understand the financial side of your life and business. And that’s what I love about your work, Bari! The way you help folks to envision what it is they want out of their bookkeeping and this allows them the incredible chance to take charge of this aspect of their lives and businesses and move into what I call a “New Financial Reality” based on the upgrade you receive when you get your books up-to-date and into the present moment.

Why do you love bookkeeping so much?

I love providing bookkeeping services to my clients because it empowers them to do their greatest work in the world. I truly do live my inspiration for my business: I do what I do for you so that you can do what you are called to do. I love how the simple act of inputting numbers into a computer on a regular basis (and obviously all the other aspects that come into play with business accounting) can be the doorway to a source of endless treasure in the form of knowledge and insight into your business and life. I love that I’ve been gifted with the ability to understand, implement, and maintain bookkeeping records for businesses and all that goes along with that, and that by doing so I’ve also been able to support small business owners over the years in ways they may never have been supported had they not found a love of bookkeeping by way of enjoying and leveraging my services. And I truly love that this once-so-commonly-ignored aspect of small business is now being talked about in much wider forums and people seem to be embracing this truly freedom-inducing, power-inspiring, insight-providing aspect of being in business.

Do you prefer to do all of the bookkeeping for me? Or do you want me to jump in for parts?

I want to do as much or as little of the bookkeeping as you need me to do in order to elevate your success and enjoyment of being in business. If you’re finding that NOTHING is getting done, I want you to learn how to pay your bills regularly in a systematic and easy way, and I want you to let me do “everything” else. If you are in a circumstance that feels like you need a lot of help, I’m here to offer a lot of help. If you feel like you’re just getting snagged up on this one odd thing, well I’m here to help with that as well. My entire process of exploring working together involves sorting out what it would look like to work together. And we paint that picture and envision the ideal reality together. I will help you understand what you’re missing or needing in your bookkeeping practices and then we will design and implement a system that supports you in all the right ways, with nothing overlooked and everything handled to contribute to your success.

Are you open to teaching me as well? 

Absolutely. I am open to teaching and sharing anything and everything I know about money, bookkeeping, and being in business. I consider myself to be a natural teacher, and I find great joy in giving people the gift of acquiring tools that contribute to a more joyful experience in business and life.

Are you good at explaining concepts that seem complex to me? 

Believe it or not, that ability is pretty much one of my super powers. In fact, one of my positions early in my career was as a Computer Programmer/Analyst at a health insurance company and I was the go-to-programmer for speaking the language that could bridge between the end users (in this case nurses) and the technology crew (in this case my co-workers). So yes, I am actually deeply appreciative of the aspects of my life path that ensured I learned how to use two diverse sets of skills in such a way that I actually can translate accounting and any related business concepts, into something much more accessible terms, understandable ideas, and, in some cases, even more appealing concepts!

Do you work with the creative community? Do you know how to speak our language? 

One of the things people always say they love about me is my ability to connect with anyone, anywhere, at any time. I am really great at getting to know you, learning about who you are and what it is you do, and learning all about your business, and then being able to connect with you in such a way that your language and my language are the same.

16 Interview Questions for Bookkeepers

If you do decide to go ahead and hire a bookkeeper, here is a list of solid questions to bring with you. Hearing their answers will help clarify who you want to work with, and what exactly they will do for you. 

  1. Do you have advice/suggestions to give someone to help them decide if they are ready to hire a bookkeeper or do it themselves.
  2. How long have you been doing this bookkeeping thing?
  3. How did you start and what is your training?
  4. What do you love about bookkeeping so much?
  5. Do you prefer to do all of the bookkeeping for me? Or do you want me to jump in for parts?
  6. Are you open to teaching me as well?
  7. Are you good at explaining concepts that seem complex to me?
  8. Do you think we’re a good match? What kind of clients do you like to work with?
  9. Do you work with the creative community? Do you know how to speak our language?
  10. Or do you work with attorneys, or …(name your particular field), as there are specific nuances to my accounting that are essential for you to know?
  11. Do you offer bookkeeping for personal and business?
  12. Do you offer virtual bookkeeping or at my home?
  13. If you offer virtual bookkeeping, how do you get my info?
  14. What are you favorite accounting programs? For personal finances? Biz finances?
  15. Can you help me choose the best bookkeeping system for my needs?
  16. What types of questions do you ask to help me choose the best system? (e.g. what features am I looking for? needs? preferences? etc)

Pause. Zoom Out. 

If you can feel yourself beginning to contract, beginning to spin, or check out — please do not forget our trusty Body Check Ins as we approach this work. 

Here’s a quick story from a student of mine who learned first hand how essential this piece is: 

“When people are interviewing a bookkeeper they would benefit by doing a body check-in during the interview. The first bookkeeper I interviewed came very highly recommended. At the interview, I noticed something did not feel right. I reacted strongly to her way of speaking to me. I left the interview feeling anxious and agitated and unsettled. I over-rode my intuition and STILL offered her the work! Thankfully, she disappeared into thin air before we even got started. She never returned any of my phone calls after the interview. It was a blessing! Because I ended up with a fantastic bookkeeper. When I interviewed the 2nd bookkeeper, it felt right from the first moment. She “gets” me & my business, has a positive attitude, and was willing to educate me about Quicken and banking. This was my first lesson in following my intuition in my business decisions. You have to be able to work with the person….it’s an intimate business relationship and it has to be the right fit.”

Remember, there is no one way to do your money relationship. There are many, many ways to forge a conscious money relationship, and the goal is to make a self-loving choice with awareness. The goal is not to make the perfect choice, because there is no such thing. You may make different bookkeeping choices for your personal, couple, or business finances — and you may choose to shift them down the line. All of this is good. The point is to stay awake as your money relationship evolves. Capish? Capish.

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