October 20, 2025 • 22 mins
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.
Other ways to connect with me:
Come learn with me in my monthly workshops
➡️ Join here
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➡️ Schedule your free clarity call here
From my soul to yours,
Erin
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Erin Gray (00:00):
Today on the podcast, I am going to be sharing with
you the questions that I wouldbe asking if I was on a call
with you when hiring your eitherfirst bookkeeper or if you're
switching to someone else.
So I'm going to share with youall of my thoughts on
bookkeepers, hiring one, andalso the questions that you need
to be asking.
So let's dive in.
(00:20):
Okay, so as some of you alreadyknow, if you've been here a
while, you know my history ofworking in my family's
construction business for over10 years.
And so the depth and breadth ofknowledge that I have in
QuickBooks is immense to put itvery lightly.
I am very well versed inQuickBooks desktop, I should
(00:42):
say, because when at my family'sconstruction business, we did
uh, I think it was calledcontractors edition, but it was
a very robust system.
Like if you have QuickBooksDesktop, which a lot of us don't
anymore, that you know, we've alot of us have moved to
QuickBooks Online, but if youhave just QuickBooks Desktop, I
am 100% able to like, I couldwalk you through things by me
just being on the phone withyou, not even looking at the
(01:03):
screen because I just know it sowell.
And I say that to say that Ican only imagine the overwhelm
that you might actually feelwhen trying to sit down and look
at your books or talk to abookkeeper or even your CPA.
Because first and foremost,you're trying to, you know,
understand the language ofQuickBooks.
(01:24):
Like it is, it is a language.
Two, you're trying tounderstand accounting, which
let's just be honest.
I mean, I took accounting in abunch of finance classes in
college and you know, throughoutmy life.
And it's not necessarilylanguage that is like very uh
supportive to learning, youknow, it's like they they use
different words for the samething, like income and revenue.
(01:45):
It's all the same.
Like, why can't we just make itso simple and not make it
complex?
That's another topic foranother day.
So, you know, you've got yourlanguage of QuickBooks, you have
the language of accounting, andthen you also have just, you
know, trying to understand howto read reports.
So I just want to say, like,you are doing it, you are like
(02:07):
take go easy on yourself becausethis isn't something that is
taught, and we're kind of havingto learn this and also run a
business.
So give yourself some grace.
So before I get into thequestions that I would be asking
if I was on a call with you, orthe questions that I would
recommend if you were my clientto be asking a bookkeeper, first
and foremost, with anything, Ialways start from in the
(02:30):
energetic piece.
Like you have to like who youwork with.
The other day I was actuallycalling for um, because my
husband is um starting a treebusiness.
And so I was calling differentinsurance agents.
And I was on the phone withthis one lady and I could just
feel my body tense up.
(02:52):
And my husband was sittingright next to me because he's
learning that back in process.
And I had to take a breath andpause and be like, hang on a
second, do you evenenergetically 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 tointerview two to three people
(03:14):
first and foremost, and see howyou feel in your body and
energetically when you work withthem.
Because these are going to bepeople that I always like, I
advise my clients, these arepeople that you are going to
work with for an extended, along period of time.
Like ideally, you want to workwith them and grow and scale
with them and years and years,right?
Down the road.
(03:35):
Now, things happen and youknow, people change, but you
know, careers or whatever itmight be, but like really, it's
not just somebody who's justgoing to like, you're gonna give
them numbers and they're gonnaput the numbers in and they're
gonna just spit them back out atyou.
Like it's more than that.
It is a relationship.
I think it's an intimaterelationship with not just your
bookkeeper, but anybody that youhire.
So, first and foremost, bethinking about what is, how do I
(03:59):
feel when I'm with this person?
Does this person seem like theylike enjoy their job and have
fun?
Like there's been CPAs that Iwon't hire because they just
feel like they just hate life,you know?
So I don't want to be aroundsomebody like that.
Like I want somebody that likestheir job, likes teaching me,
likes to be, you know,supporting and serving clients.
So that is first and foremostthe question that I would ask
(04:20):
you is like, do you actuallyenjoy being with this person,
talking to them?
Do you feel like that theywould be a good mentor for you?
Or do they you feel likethey're just trying to, you
know, check the box, get the getthe reports out and and be
done?
So that would be my first andforemost like question I would
ask you.
Now, as we're going to diveinto like the questions to ask
(04:42):
your bookkeeper, I want to alsoback up and say here that it is
extremely important that youactually know your books.
And I know that that can feellike a lot when you're trying to
grow your business, but I trulybelieve, and I've seen this
with clients, if you don't takethe time to sit down and
understand your books, there's acouple of things that happen.
Number one, you're gonna takeyourself wherever you go and
(05:05):
grow with your business.
So if you don't understand yourbooks now, what do you think,
what makes you think you'regonna understand them when
you're doing millions, 10millions, 100 million in
revenue?
This is one of thosefoundational things that you
need to sit down and take thetime, even though your brain
might tell you, uh, it's youknow, it's taken away from XYZ.
This is a foundational skillset that once you know this,
(05:26):
then you can offload it tosomeone else and you can know
what you are offloading.
And you know, when someonequotes you prices, you know how
long it takes, you know thevalue you're receiving or not
receiving.
And I think it's a reallyimportant skill set to have.
You can learn from like there'sso many YouTube videos.
There's even like check likeyour local SBA.
(05:49):
They even have like, I'm on mylocal in Boise, I'm on my SBA
email list, and I see all thetime 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 theaccountant.
(06:10):
Now, accountants andbookkeepers typically don't mesh
in terms of like they don't dothe other person's job, but
there would be questions that Iwould ask about numbers and I
would just pay for an hour ofher time to ask and dig deeper
into the questions so I couldunderstand it better.
And I think that that type ofinvestment that we spend to
understand things at a deeperlevel is so important and
(06:32):
valuable.
So, with all of that said,let's dive into actually the
questions that I would be askingif I was hiring a bookkeeper or
I was on the phone with you, oryou were my client and I was
like, hey, these are thequestions to ask the bookkeeper.
First and foremost, what istheir actual experience in
working with your type ofbusiness?
So I have clients that haveonline businesses, I have
(06:55):
clients that have brick andmortar businesses.
And those types of businesses,brick and mortar or online, are
very types of, they're differenttypes of businesses.
So cash flow is different,profitability can be different.
So it really matters that yourbookkeeper is versed, number
one, first and foremost, like inthe industry that you are
(07:16):
actually in.
So if they are not used toworking with your industry, how
can they advise you and likeproject things that might be
coming up for you and mentor youif they don't have any clients
that are in the industry thatyou're in?
So I would ask first andforemost, what experience do you
have working with businesseslike mine?
The second question that Iwould ask is most bookkeepers
(07:39):
typically use QuickBooks becausea lot of accountants like to
use QuickBooks, but justobviously verify that that is
what they use and also ask themlike, what is their workflow?
So, meaning, like, are theygoing to retrieve online
statements for you and thenthey're gonna reconcile all of
your accounts?
(07:59):
Or is it your responsibility tosend them the statements and
then they are the ones that trueit up?
So, really just asking themwhat is an actual month look
like of us working together soyou get an idea of what you can
expect with working with them.
And also then you can ask moreclarifying questions if it's not
(08:20):
maybe you want more supportthan that.
So maybe even though you maynot have a whole lot of maybe
say transactions to do oraccounts to reconcile, if you're
wanting more support or you'rewanting to be handheld a little
bit more, maybe you actuallyneed to pay for more time with
them.
So just really asking aboutlike what is their workflow,
(08:40):
what do they expect from you asa client?
And what do you expect fromthem as a bookkeeper?
The third thing that I wouldalso ask is a lot of us, whether
you're online or you are brickand mortar, a lot of us use like
a payment processor, right?
Like I use Stripe as my paymentprocessor.
I used to use QuickBooks whenthey allowed with desktop.
Some people use other types ofpayment processors.
(09:04):
So if your bookkeeper thatyou're interviewing isn't
familiar with that, okay, firstand foremost, know that.
And then if you really likethem and they just don't know
that, but they're willing tolearn the payment processing,
how are they actually going tolike bring that into QuickBooks?
Are they going to keep itseparate?
Because sometimes it actuallymakes sense to keep it separate
(09:25):
because the way that QuickBooksworks is it can like do double
entries and sometimes it justgets really messy.
Like on the one hand,QuickBooks is like a really
robust system.
And then at the same time, it'slike, oh my gosh, who, who,
who, who thought of this?
Because there's so many thingsthat sometimes QuickBooks, I'm
like, what are you thinking?
But so if they're gonna keep itseparate and they're not gonna
(09:46):
bring it in, are they actuallygoing 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 agroup and my one-on-one clients,
and let's say I also had paidworkshops or I um had retreats
or something like that, like Ipersonally would want to know
(10:08):
income in each of those areas soI could see what is my
profitability in each of thosethings.
So the same goes for you.
So you want to be able to seealong with your income and your
expenses, so you can pullreports to actually see like
what is profitable.
Because if you're continuing todo a service that isn't
profitable, then that's a that'sinformation and data that you
(10:29):
need to make a decision.
Now, I always say go with yourgut.
And also, like if you don'tknow, you don't know and you
can't like actually makeinformed decisions.
So, how are they actually goingto enter the data for you for
your payment processor?
Because so many of us usecredit cards.
And so are they gonna, youknow, break all of that down for
you, or are they just gonnabring it in and lump some, just
(10:51):
like income?
And if they are gonna just doincome, I would advise you to
push back and be like, I want tobe able to see my individual
income.
Cause here's the thing I thinkabout too, is you're not just
setting it up for right now.
Like you have to think aboutyou as the business owner three,
five, 10 years from now.
And that's who you need to beacting from and interviewing
(11:12):
from.
So, you know, if you have abookkeeper who's like, oh, well,
we'll just, you know, crossthat bridge when we get there.
No, I actually want to set itup correctly now so that I grow
with it and I can see.
So be really clear on that.
Um, are they going to break itdown for you?
Are they going to break costsdown for you?
Things of that sort.
The third, or maybe the fourthquestion, you know, how often
(11:34):
are you going to be able tocommunicate?
What I've seen with some, howdo I say this?
Lower investment um prices,like with working with book,
like the entry-level bookkeepingthat's you might be doing with
someone is they they aren'treconciled a lot of accounts,
like maybe two or three, andthey typically don't get on the
phone with you, which I get it.
Like you pay for their time andtheir knowledge, but just be
(11:59):
aware of that.
Like, what does your package, alot 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 toreconcile, but you want to be
able to talk to them once amonth and they're like, Well, I
don't talk once a month, youknow, like I just send you your
reports in an email, then thatmight not be the fit that you
(12:21):
want, or you just might have tobe to decide to choose to pay a
little bit more with them inorder to get a phone call or a
Zoom call or something likethat.
So some bookkeepers do monthlyreports, others offer weekly
updates.
Again, this is based on likeprobably the revenue of your
business, the complexity of yourbusiness.
And when I say complexity, whatI mean is like the number of
(12:43):
accounts and transactions andthings to reconcile.
So this goes back to like thepricing of the service and you
know, what is their kind of theythey typically have like three
or four packages.
So, really, you know, beingclear on what are they going to
here?
We go back to expectations.
What are you expecting fromthem and what are they expecting
(13:05):
from you?
And does that actually align?
So if you're wanting someone tobe on the phone, then you need
to state that up front and youknow, either pay for that extra
or find somebody that will dothat for you.
Other things that I would thinkabout is are they gonna file
sales tax for you if you dosales tax?
Do they true up what I meanwhen I say true up with your
loan agreements?
Is are they going to wait untilthe end of the year to itemize
(13:29):
or categorize, you know, yourprincipal and your interest if
you have a loan?
Or are they gonna do that on amonthly basis so you can see a
true, you know, standing ofwhere you are?
Like I always in my family'sconstruction business, anytime
we had a loan agreement, Ialways did that monthly because
I wanted to know, and it alsosaves a lot of time on the back
end because you don't have to dojournal entries.
(13:51):
You know, I always liked to seewhere we are with our actual
loan agreements or loan paymentsand what was our principal and
what have we paid to interest.
So, same thing goes for creditcard reconciliation.
So it's just important to askthem how many accounts are being
reconciled in the level ofservice that they are actually
providing.
Okay, so number four, I would,and a lot of times they have
(14:15):
like it written either on theirwebsite or um if they give you a
scope of work, it's there.
But like what's actuallyincluded in your services and
what would be an additionalcost?
So, like I said before, somebookkeepers, you know, track
your income and your expenseswhile others might be helping
you do, you know, invoicing orpayroll, or they work with the
(14:38):
CPA to do tax prep.
So just make sure that you knowwhat is covered so that you're
not, you know, getting towardsthe end of the year and you're,
you know, you're three months inand 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 whatthey call a portal.
The same thing goes for CPAs.
(14:59):
It's a typically most of thetime, it is a secure portal, but
you want to ask that questionis it a secure portal?
And is that how theycommunicate with you?
And that's where you can uploadyour documents.
Like, you do not want to besending your documents with your
Gmail or your, you know, workemail.
Like, I don't ever sendanything that has social
security or just anything.
Like if they're a bookkeeper orthey're a CPA, they need to
(15:20):
have a portal.
You need to be able, it needsto be secure and you need to be
able to have your own login andyou 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 isI ask all the questions.
And what I tell my clients is Ialways like to, when I'm
(15:40):
interviewing someone, I willtell them, like, I will pay you
for your hour of time.
I don't expect you to just haveendless consultations for free.
But I want to be able to havean hour with you to ask my
questions so that I can get themall answered versus feeling
rushed to make a decision.
And then I'm already in anagreement with you, and then I
find out I don't really like,you know, your services or the
way you're speaking to me orsomething like that.
(16:02):
So I always advise clients likeit is worth every single penny
that you would pay an attorneyfor a consultation if they
charge for a CPA and or abookkeeper and insurance agents.
But I mean, I would justanybody that is gonna be helping
you with your business, Ialways start that off.
Like, hey, would love to have aconsultation with you, be happy
to pay for you.
I mean, even people I've had inmy business, like with um video
(16:25):
editing or people that I've,you know, were gonna help me
with some website stuff.
Like, I'll be happy to pay youfor, you know, the time that
we're gonna spend on the calljust so I can ask my questions.
And I think it's money reallywell spent because then you get
to see and you get to really getyour answers clarified and it's
well worth the investment.
Okay, so number five is do theyactually work with your CPA and
(16:47):
do they talk with them?
Or are you expected to be themiddleman between both of them?
So I have yet to meet a CPAthat actually knows bookkeeping.
And so and that's not reallytheir job, really, right?
Like they they really are forthe taxes and the planning.
So I get that.
(17:08):
But if you do not have abookkeeper who is talking to
your CPA and who you are talkingto all three of them, or all
three of you are talking, then Ithink sometimes things get lost
in translation, or someonethinks somebody else is doing it
versus like I had a client andI asked her about closing out
year end.
And I was like, Well, how didyour CPA do that if your
(17:30):
bookkeeper told you that itwasn't closed out?
And she was like, Well, I don'tknow.
And then she goes back and asksthe CPA, and the CPA is like,
Well, I just assumed that it wasclosed out.
No, not an okay answer for me.
You know, I told my client, I'mlike, absolutely not.
Like, we need to come back toyour CPA and your bookkeeper and
be like, okay, let's draw some,you know, expectations here
(17:50):
because do not assume anything.
You need to ask me questions.
So maybe that's because CPAsdon't want to ask the questions.
Maybe it's because they don'twant to feel like they have to
ask and then they're gonnacharge 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 veryclear on expectations because
don't assume.
Like, I don't want to work withanybody that just assumes, do
(18:13):
not assume.
Making sure that your CPA andyour bookkeeper are talking to
each other and that, you know,this is more so CPA of like
doing tax planning.
But with your bookkeeper, likethere's a there's a place in
QuickBooks where it says ask theaccountant.
And I have seen somebookkeepers, if they don't know,
they'll just file it, they'llcategorize it under there
(18:34):
instead of picking up the phoneor sending you an email and
being like, hey, what is thischarge?
Where does it need to go?
So then at year end, you haveall of these questions for ask
my accountant when these arethings that could have been done
and taken care of all along theyear.
So just be really clear like,what is your relationship like
with either CPAs that you workwith if you're looking for a new
(18:56):
CPA, or I have a CPA already?
What is your, you know,feelings and thoughts on working
with my CPA and workingclosely, like on a quarterly
basis, so we can make sure weare, you know, knowing where we
are versus the end of the year.
Okay.
And then the last one I wouldsay is how do you ensure
accuracy?
(19:16):
And like we already kind oftalked about this, is like
securing the financial data,right?
So they're taking care of yourfinancial information, it's
sensitive information.
So QuickBooks, like, what istheir system to, you know, we
already talked about the portal,but like QuickBooks, who else
has access?
Like sometimes bookkeepers willhave other bookkeepers that
work for them.
(19:36):
So the person that you'retalking to, and this goes for
CPAs too.
So this is a bonus for you.
Whether you're interviewingyour bookkeeper or your CPA, the
question that you need to askis Am I gonna be talking to you
when it comes time for my booksand for my taxes?
Because sometimes the questionis no, or excuse me, the answer
is no.
Actually, you're gonna beworking with my, you know,
(19:56):
newbie CPA that I just hired on,which I've had that
conversation before as well.
That's not a problem, but I'mnot gonna pay your 25-year rate
of you CPA when I'm teaching andtraining your new CPA.
And also, I'm not gonna bespending time teaching and
training above and beyond whatjust simple answers are, because
(20:17):
let's just be honest, that'skind of your job.
So, really being very crystalclear of like, hey, are you
gonna be the one doing my books?
Or am are you the face of thecompany 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?
(20:38):
Okay.
And then a bonus one for youis, 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'mlooking for.
Like, what is your protocol?
Period.
Like, tell me.
Like, do I don't expect you toanswer my calls on vacation?
(20:59):
And let's just be honest,bookkeeping, it there's not
really that much.
Like, you know, withbookkeeping, there's not a lot
of things that like have tohappen right now.
But like if they go out of townduring, let's just say,
typically they wouldn't, butlet's just say that they were
going out of town during likesubmitting your sales tax, or
you know, when you go on whenyou do payroll.
(21:20):
I don't know.
It's just really being clear,like, what is their backup for
you?
Because everybody deserves togo on vacation.
Everybody deserves to take timeoff.
And you also deserve to be ableto have someone support you
while someone else is onvacation.
Okay, that felt like a lot.
I know.
So go back, listen to thisepisode multiple times.
Take your pen and your piece ofpaper and write down all the
(21:42):
questions.
As you know, if you ever needsupport, want support and
mentorship along this lovelyjourney called entrepreneurship
and life, I would be happy tosupport you.
Just fill out the or click onthe link in the show notes and
you can schedule a time that wecan talk.
So, to recap, you know, whatexperiences do you have working
(22:02):
with businesses like mine?
What software are you using?
Are they understanding yourtype of payment processor?
How are you willing tocommunicate?
What is included in yourservices?
And two more.
How do you ensure the accuracyand security of my financial
data, along with what are yougoing to do when you go on
(22:24):
vacation?
Okay, it's always a pleasure.
I'm rooting for you.
Every single one of you haveevery single thing within you
already.
You are already highlysuccessful, you are already
highly prosperous and wealthy.
And I think a lot of us justneed to actually believe it.
So until next time, I'll seeyou in the next episode.
Today on the podcast, I am going to be sharing with
you the questions that I wouldbe asking if I was on a call
with you when hiring your eitherfirst bookkeeper or if you're
switching to someone else.
So I'm going to share with youall of my thoughts on
bookkeepers, hiring one, andalso the questions that you need
to be asking.
So let's dive in.
(00:20):
Okay, so as some of you alreadyknow, if you've been here a
while, you know my history ofworking in my family's
construction business for over10 years.
And so the depth and breadth ofknowledge that I have in
QuickBooks is immense to put itvery lightly.
I am very well versed inQuickBooks desktop, I should
(00:42):
say, because when at my family'sconstruction business, we did
uh, I think it was calledcontractors edition, but it was
a very robust system.
Like if you have QuickBooksDesktop, which a lot of us don't
anymore, that you know, we've alot of us have moved to
QuickBooks Online, but if youhave just QuickBooks Desktop, I
am 100% able to like, I couldwalk you through things by me
just being on the phone withyou, not even looking at the
(01:03):
screen because I just know it sowell.
And I say that to say that Ican only imagine the overwhelm
that you might actually feelwhen trying to sit down and look
at your books or talk to abookkeeper or even your CPA.
Because first and foremost,you're trying to, you know,
understand the language ofQuickBooks.
(01:24):
Like it is, it is a language.
Two, you're trying tounderstand accounting, which
let's just be honest.
I mean, I took accounting in abunch of finance classes in
college and you know, throughoutmy life.
And it's not necessarilylanguage that is like very uh
supportive to learning, youknow, it's like they they use
different words for the samething, like income and revenue.
(01:45):
It's all the same.
Like, why can't we just make itso simple and not make it
complex?
That's another topic foranother day.
So, you know, you've got yourlanguage of QuickBooks, you have
the language of accounting, andthen you also have just, you
know, trying to understand howto read reports.
So I just want to say, like,you are doing it, you are like
(02:07):
take go easy on yourself becausethis isn't something that is
taught, and we're kind of havingto learn this and also run a
business.
So give yourself some grace.
So before I get into thequestions that I would be asking
if I was on a call with you, orthe questions that I would
recommend if you were my clientto be asking a bookkeeper, first
and foremost, with anything, Ialways start from in the
(02:30):
energetic piece.
Like you have to like who youwork with.
The other day I was actuallycalling for um, because my
husband is um starting a treebusiness.
And so I was calling differentinsurance agents.
And I was on the phone withthis one lady and I could just
feel my body tense up.
(02:52):
And my husband was sittingright next to me because he's
learning that back in process.
And I had to take a breath andpause and be like, hang on a
second, do you evenenergetically 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 tointerview two to three people
(03:14):
first and foremost, and see howyou feel in your body and
energetically when you work withthem.
Because these are going to bepeople that I always like, I
advise my clients, these arepeople that you are going to
work with for an extended, along period of time.
Like ideally, you want to workwith them and grow and scale
with them and years and years,right?
Down the road.
(03:35):
Now, things happen and youknow, people change, but you
know, careers or whatever itmight be, but like really, it's
not just somebody who's justgoing to like, you're gonna give
them numbers and they're gonnaput the numbers in and they're
gonna just spit them back out atyou.
Like it's more than that.
It is a relationship.
I think it's an intimaterelationship with not just your
bookkeeper, but anybody that youhire.
So, first and foremost, bethinking about what is, how do I
(03:59):
feel when I'm with this person?
Does this person seem like theylike enjoy their job and have
fun?
Like there's been CPAs that Iwon't hire because they just
feel like they just hate life,you know?
So I don't want to be aroundsomebody like that.
Like I want somebody that likestheir job, likes teaching me,
likes to be, you know,supporting and serving clients.
So that is first and foremostthe question that I would ask
(04:20):
you is like, do you actuallyenjoy being with this person,
talking to them?
Do you feel like that theywould be a good mentor for you?
Or do they you feel likethey're just trying to, you
know, check the box, get the getthe reports out and and be
done?
So that would be my first andforemost like question I would
ask you.
Now, as we're going to diveinto like the questions to ask
(04:42):
your bookkeeper, I want to alsoback up and say here that it is
extremely important that youactually know your books.
And I know that that can feellike a lot when you're trying to
grow your business, but I trulybelieve, and I've seen this
with clients, if you don't takethe time to sit down and
understand your books, there's acouple of things that happen.
Number one, you're gonna takeyourself wherever you go and
(05:05):
grow with your business.
So if you don't understand yourbooks now, what do you think,
what makes you think you'regonna understand them when
you're doing millions, 10millions, 100 million in
revenue?
This is one of thosefoundational things that you
need to sit down and take thetime, even though your brain
might tell you, uh, it's youknow, it's taken away from XYZ.
This is a foundational skillset that once you know this,
(05:26):
then you can offload it tosomeone else and you can know
what you are offloading.
And you know, when someonequotes you prices, you know how
long it takes, you know thevalue you're receiving or not
receiving.
And I think it's a reallyimportant skill set to have.
You can learn from like there'sso many YouTube videos.
There's even like check likeyour local SBA.
(05:49):
They even have like, I'm on mylocal in Boise, I'm on my SBA
email list, and I see all thetime 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 theaccountant.
(06:10):
Now, accountants andbookkeepers typically don't mesh
in terms of like they don't dothe other person's job, but
there would be questions that Iwould ask about numbers and I
would just pay for an hour ofher time to ask and dig deeper
into the questions so I couldunderstand it better.
And I think that that type ofinvestment that we spend to
understand things at a deeperlevel is so important and
(06:32):
valuable.
So, with all of that said,let's dive into actually the
questions that I would be askingif I was hiring a bookkeeper or
I was on the phone with you, oryou were my client and I was
like, hey, these are thequestions to ask the bookkeeper.
First and foremost, what istheir actual experience in
working with your type ofbusiness?
So I have clients that haveonline businesses, I have
(06:55):
clients that have brick andmortar businesses.
And those types of businesses,brick and mortar or online, are
very types of, they're differenttypes of businesses.
So cash flow is different,profitability can be different.
So it really matters that yourbookkeeper is versed, number
one, first and foremost, like inthe industry that you are
(07:16):
actually in.
So if they are not used toworking with your industry, how
can they advise you and likeproject things that might be
coming up for you and mentor youif they don't have any clients
that are in the industry thatyou're in?
So I would ask first andforemost, what experience do you
have working with businesseslike mine?
The second question that Iwould ask is most bookkeepers
(07:39):
typically use QuickBooks becausea lot of accountants like to
use QuickBooks, but justobviously verify that that is
what they use and also ask themlike, what is their workflow?
So, meaning, like, are theygoing to retrieve online
statements for you and thenthey're gonna reconcile all of
your accounts?
(07:59):
Or is it your responsibility tosend them the statements and
then they are the ones that trueit up?
So, really just asking themwhat is an actual month look
like of us working together soyou get an idea of what you can
expect with working with them.
And also then you can ask moreclarifying questions if it's not
(08:20):
maybe you want more supportthan that.
So maybe even though you maynot have a whole lot of maybe
say transactions to do oraccounts to reconcile, if you're
wanting more support or you'rewanting to be handheld a little
bit more, maybe you actuallyneed to pay for more time with
them.
So just really asking aboutlike what is their workflow,
(08:40):
what do they expect from you asa client?
And what do you expect fromthem as a bookkeeper?
The third thing that I wouldalso ask is a lot of us, whether
you're online or you are brickand mortar, a lot of us use like
a payment processor, right?
Like I use Stripe as my paymentprocessor.
I used to use QuickBooks whenthey allowed with desktop.
Some people use other types ofpayment processors.
(09:04):
So if your bookkeeper thatyou're interviewing isn't
familiar with that, okay, firstand foremost, know that.
And then if you really likethem and they just don't know
that, but they're willing tolearn the payment processing,
how are they actually going tolike bring that into QuickBooks?
Are they going to keep itseparate?
Because sometimes it actuallymakes sense to keep it separate
(09:25):
because the way that QuickBooksworks is it can like do double
entries and sometimes it justgets really messy.
Like on the one hand,QuickBooks is like a really
robust system.
And then at the same time, it'slike, oh my gosh, who, who,
who, who thought of this?
Because there's so many thingsthat sometimes QuickBooks, I'm
like, what are you thinking?
But so if they're gonna keep itseparate and they're not gonna
(09:46):
bring it in, are they actuallygoing 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 agroup and my one-on-one clients,
and let's say I also had paidworkshops or I um had retreats
or something like that, like Ipersonally would want to know
(10:08):
income in each of those areas soI could see what is my
profitability in each of thosethings.
So the same goes for you.
So you want to be able to seealong with your income and your
expenses, so you can pullreports to actually see like
what is profitable.
Because if you're continuing todo a service that isn't
profitable, then that's a that'sinformation and data that you
(10:29):
need to make a decision.
Now, I always say go with yourgut.
And also, like if you don'tknow, you don't know and you
can't like actually makeinformed decisions.
So, how are they actually goingto enter the data for you for
your payment processor?
Because so many of us usecredit cards.
And so are they gonna, youknow, break all of that down for
you, or are they just gonnabring it in and lump some, just
(10:51):
like income?
And if they are gonna just doincome, I would advise you to
push back and be like, I want tobe able to see my individual
income.
Cause here's the thing I thinkabout too, is you're not just
setting it up for right now.
Like you have to think aboutyou as the business owner three,
five, 10 years from now.
And that's who you need to beacting from and interviewing
(11:12):
from.
So, you know, if you have abookkeeper who's like, oh, well,
we'll just, you know, crossthat bridge when we get there.
No, I actually want to set itup correctly now so that I grow
with it and I can see.
So be really clear on that.
Um, are they going to break itdown for you?
Are they going to break costsdown for you?
Things of that sort.
The third, or maybe the fourthquestion, you know, how often
(11:34):
are you going to be able tocommunicate?
What I've seen with some, howdo I say this?
Lower investment um prices,like with working with book,
like the entry-level bookkeepingthat's you might be doing with
someone is they they aren'treconciled a lot of accounts,
like maybe two or three, andthey typically don't get on the
phone with you, which I get it.
Like you pay for their time andtheir knowledge, but just be
(11:59):
aware of that.
Like, what does your package, alot 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 toreconcile, but you want to be
able to talk to them once amonth and they're like, Well, I
don't talk once a month, youknow, like I just send you your
reports in an email, then thatmight not be the fit that you
(12:21):
want, or you just might have tobe to decide to choose to pay a
little bit more with them inorder to get a phone call or a
Zoom call or something likethat.
So some bookkeepers do monthlyreports, others offer weekly
updates.
Again, this is based on likeprobably the revenue of your
business, the complexity of yourbusiness.
And when I say complexity, whatI mean is like the number of
(12:43):
accounts and transactions andthings to reconcile.
So this goes back to like thepricing of the service and you
know, what is their kind of theythey typically have like three
or four packages.
So, really, you know, beingclear on what are they going to
here?
We go back to expectations.
What are you expecting fromthem and what are they expecting
(13:05):
from you?
And does that actually align?
So if you're wanting someone tobe on the phone, then you need
to state that up front and youknow, either pay for that extra
or find somebody that will dothat for you.
Other things that I would thinkabout is are they gonna file
sales tax for you if you dosales tax?
Do they true up what I meanwhen I say true up with your
loan agreements?
Is are they going to wait untilthe end of the year to itemize
(13:29):
or categorize, you know, yourprincipal and your interest if
you have a loan?
Or are they gonna do that on amonthly basis so you can see a
true, you know, standing ofwhere you are?
Like I always in my family'sconstruction business, anytime
we had a loan agreement, Ialways did that monthly because
I wanted to know, and it alsosaves a lot of time on the back
end because you don't have to dojournal entries.
(13:51):
You know, I always liked to seewhere we are with our actual
loan agreements or loan paymentsand what was our principal and
what have we paid to interest.
So, same thing goes for creditcard reconciliation.
So it's just important to askthem how many accounts are being
reconciled in the level ofservice that they are actually
providing.
Okay, so number four, I would,and a lot of times they have
(14:15):
like it written either on theirwebsite or um if they give you a
scope of work, it's there.
But like what's actuallyincluded in your services and
what would be an additionalcost?
So, like I said before, somebookkeepers, you know, track
your income and your expenseswhile others might be helping
you do, you know, invoicing orpayroll, or they work with the
(14:38):
CPA to do tax prep.
So just make sure that you knowwhat is covered so that you're
not, you know, getting towardsthe end of the year and you're,
you know, you're three months inand 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 whatthey call a portal.
The same thing goes for CPAs.
(14:59):
It's a typically most of thetime, it is a secure portal, but
you want to ask that questionis it a secure portal?
And is that how theycommunicate with you?
And that's where you can uploadyour documents.
Like, you do not want to besending your documents with your
Gmail or your, you know, workemail.
Like, I don't ever sendanything that has social
security or just anything.
Like if they're a bookkeeper orthey're a CPA, they need to
(15:20):
have a portal.
You need to be able, it needsto be secure and you need to be
able to have your own login andyou 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 isI ask all the questions.
And what I tell my clients is Ialways like to, when I'm
(15:40):
interviewing someone, I willtell them, like, I will pay you
for your hour of time.
I don't expect you to just haveendless consultations for free.
But I want to be able to havean hour with you to ask my
questions so that I can get themall answered versus feeling
rushed to make a decision.
And then I'm already in anagreement with you, and then I
find out I don't really like,you know, your services or the
way you're speaking to me orsomething like that.
(16:02):
So I always advise clients likeit is worth every single penny
that you would pay an attorneyfor a consultation if they
charge for a CPA and or abookkeeper and insurance agents.
But I mean, I would justanybody that is gonna be helping
you with your business, Ialways start that off.
Like, hey, would love to have aconsultation with you, be happy
to pay for you.
I mean, even people I've had inmy business, like with um video
(16:25):
editing or people that I've,you know, were gonna help me
with some website stuff.
Like, I'll be happy to pay youfor, you know, the time that
we're gonna spend on the calljust so I can ask my questions.
And I think it's money reallywell spent because then you get
to see and you get to really getyour answers clarified and it's
well worth the investment.
Okay, so number five is do theyactually work with your CPA and
(16:47):
do they talk with them?
Or are you expected to be themiddleman between both of them?
So I have yet to meet a CPAthat actually knows bookkeeping.
And so and that's not reallytheir job, really, right?
Like they they really are forthe taxes and the planning.
So I get that.
(17:08):
But if you do not have abookkeeper who is talking to
your CPA and who you are talkingto all three of them, or all
three of you are talking, then Ithink sometimes things get lost
in translation, or someonethinks somebody else is doing it
versus like I had a client andI asked her about closing out
year end.
And I was like, Well, how didyour CPA do that if your
(17:30):
bookkeeper told you that itwasn't closed out?
And she was like, Well, I don'tknow.
And then she goes back and asksthe CPA, and the CPA is like,
Well, I just assumed that it wasclosed out.
No, not an okay answer for me.
You know, I told my client, I'mlike, absolutely not.
Like, we need to come back toyour CPA and your bookkeeper and
be like, okay, let's draw some,you know, expectations here
(17:50):
because do not assume anything.
You need to ask me questions.
So maybe that's because CPAsdon't want to ask the questions.
Maybe it's because they don'twant to feel like they have to
ask and then they're gonnacharge 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 veryclear on expectations because
don't assume.
Like, I don't want to work withanybody that just assumes, do
(18:13):
not assume.
Making sure that your CPA andyour bookkeeper are talking to
each other and that, you know,this is more so CPA of like
doing tax planning.
But with your bookkeeper, likethere's a there's a place in
QuickBooks where it says ask theaccountant.
And I have seen somebookkeepers, if they don't know,
they'll just file it, they'llcategorize it under there
(18:34):
instead of picking up the phoneor sending you an email and
being like, hey, what is thischarge?
Where does it need to go?
So then at year end, you haveall of these questions for ask
my accountant when these arethings that could have been done
and taken care of all along theyear.
So just be really clear like,what is your relationship like
with either CPAs that you workwith if you're looking for a new
(18:56):
CPA, or I have a CPA already?
What is your, you know,feelings and thoughts on working
with my CPA and workingclosely, like on a quarterly
basis, so we can make sure weare, you know, knowing where we
are versus the end of the year.
Okay.
And then the last one I wouldsay is how do you ensure
accuracy?
(19:16):
And like we already kind oftalked about this, is like
securing the financial data,right?
So they're taking care of yourfinancial information, it's
sensitive information.
So QuickBooks, like, what istheir system to, you know, we
already talked about the portal,but like QuickBooks, who else
has access?
Like sometimes bookkeepers willhave other bookkeepers that
work for them.
(19:36):
So the person that you'retalking to, and this goes for
CPAs too.
So this is a bonus for you.
Whether you're interviewingyour bookkeeper or your CPA, the
question that you need to askis Am I gonna be talking to you
when it comes time for my booksand for my taxes?
Because sometimes the questionis no, or excuse me, the answer
is no.
Actually, you're gonna beworking with my, you know,
(19:56):
newbie CPA that I just hired on,which I've had that
conversation before as well.
That's not a problem, but I'mnot gonna pay your 25-year rate
of you CPA when I'm teaching andtraining your new CPA.
And also, I'm not gonna bespending time teaching and
training above and beyond whatjust simple answers are, because
(20:17):
let's just be honest, that'skind of your job.
So, really being very crystalclear of like, hey, are you
gonna be the one doing my books?
Or am are you the face of thecompany 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?
(20:38):
Okay.
And then a bonus one for youis, 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'mlooking for.
Like, what is your protocol?
Period.
Like, tell me.
Like, do I don't expect you toanswer my calls on vacation?
(20:59):
And let's just be honest,bookkeeping, it there's not
really that much.
Like, you know, withbookkeeping, there's not a lot
of things that like have tohappen right now.
But like if they go out of townduring, let's just say,
typically they wouldn't, butlet's just say that they were
going out of town during likesubmitting your sales tax, or
you know, when you go on whenyou do payroll.
(21:20):
I don't know.
It's just really being clear,like, what is their backup for
you?
Because everybody deserves togo on vacation.
Everybody deserves to take timeoff.
And you also deserve to be ableto have someone support you
while someone else is onvacation.
Okay, that felt like a lot.
I know.
So go back, listen to thisepisode multiple times.
Take your pen and your piece ofpaper and write down all the
(21:42):
questions.
As you know, if you ever needsupport, want support and
mentorship along this lovelyjourney called entrepreneurship
and life, I would be happy tosupport you.
Just fill out the or click onthe link in the show notes and
you can schedule a time that wecan talk.
So, to recap, you know, whatexperiences do you have working
(22:02):
with businesses like mine?
What software are you using?
Are they understanding yourtype of payment processor?
How are you willing tocommunicate?
What is included in yourservices?
And two more.
How do you ensure the accuracyand security of my financial
data, along with what are yougoing to do when you go on
(22:24):
vacation?
Okay, it's always a pleasure.
I'm rooting for you.
Every single one of you haveevery single thing within you
already.
You are already highlysuccessful, you are already
highly prosperous and wealthy.
And I think a lot of us justneed to actually believe it.
So until next time, I'll seeyou in the next episode.
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