Got a question? Send me a text.
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
Want to learn more? Here are your next steps:
Step 1: Join my FREE Facebook Community.
Connect, share, and learn how to master your money with other women just like you.
➡️ Join here: https://www.facebook.com/groups/941450038160915
Step 2: Grab your FREE Human Design chart
Curious what your Human Design chart reveals about how you're uniquely designed to make aligned financial decisions?
➡️ Get your chart here: https://generatealifewelllived.com/receive-your-human-design-chart
Step 3: Ready to transform your relationship with money and build true financial confidence?
Let’s create a strategy that feels aligned, intentional, and empowering—just for you.
➡️ Schedule your 1-hour Money Mastery Call here: https://generatealifewelllived.com/11-support
Money doesn't have to feel overwhelming. Let's create a strategy that feels nurturing and custom to you.
From my soul to yours,
Erin
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Erin Gray (00:00):
On today's podcast, we're going to be talking about
hiring a bookkeeper,specifically, the five essential
questions I think you need tobe asking before bringing
someone onto your team.
Whether you're hiring yourfirst bookkeeper or you're
looking to switch to someone new.
These questions are going tohelp you be able to find the
right fit for you.
Do you want to create a systemto stop avoiding your money?
(00:20):
Maybe you're feeling guilt andshame when it comes to finances.
Welcome to your Money, yourRules.
I'm Erin, a former certifiedfinancial planner and CFO, and
yet I used to avoid my money andhad fear, no matter how much we
had.
I can't wait to teach you how Iovercame my money avoidance and
started consistently managingmy finances in a really simple
(00:42):
way.
It's time to get comfortablewith money.
Before we dive into this week'sepisode, I want to invite you
to join me for a one-on-onemaster your money coaching
session.
During this hour, we'll worktogether to create a tailored
plan that helps you align yourfinances with your unique goals,
energy and mindset.
If you're ready to transformyour relationship with money and
(01:03):
create the freedom andabundance you deserve, head over
to my website,generatealifewelllivedcom and
schedule your session.
So let's talk all thingsbookkeeper.
To be completely transparent, Istill do my own books.
I learned the hard way withQuickBooks on what's called
QuickBooks Enterprise.
It's a desktop edition which isfor construction, and it might
(01:26):
be some of the toughest softwareto understand.
And yet, because I always loveto talk about how we learn
through obstacles, I am sograteful that I learned on some
of the hard stuff, because nowI'm able to look at clients'
reports in such a minimal amountof time, because I spent 10
years doing it in my family'sconstruction business.
(01:47):
I mean, I can only imagine theoverwhelm that some of you might
be feeling trying to learn thelanguage of QuickBooks or trying
to read reports, and so I wantto dive into.
You know a bookkeeper isn't justsomeone like that tracks your
numbers to.
You know a bookkeeper isn'tjust someone like that tracks
your numbers.
There's someone that you'regoing to trust with your
(02:08):
financial data and someone who'sgoing to help you.
I view everyone on your team assomeone that's helping you get
to where you want to go, and soasking the right questions
upfront, I think, is going tosave you so many headaches later
.
And this might sound like I'mtalking out of both sides of my
(02:31):
ass, so bear with me here.
On the one hand, I totallythink that you should know how
to do QuickBooks and howQuickBooks works, because the
more you know, the better you'reable to converse with your
bookkeeper and your CPA Likeyou're speaking the same
language're able to conversewith your bookkeeper and your
CPA Like you're speaking thesame language as them.
(02:51):
And then, on the flip side ofthat, I also get that it's like
a foreign language and thatspending time learning it can
feel very overwhelming andcumbersome.
So, for those of you that feelthis way, I just want you to
ponder taking some courses,watching some YouTube videos,
asking your local you can evenask your local SBA community.
They typically have classes ata lower cost that you can pay
for Um, or you can even pay yourbookkeeper for some upper level
(03:16):
training.
I know that when I was trying tounderstand in Texas, we have
something that's calledfranchise tax, which is above
and beyond federal taxes orstate taxes, and when I came
into the business, I thoughtwhen I started diving into
franchise tax, I thought that wewere totally overpaying which
we were and so I really starteddiving in to it.
(03:38):
I taught a lot of it myself,but then I would pay the CPA for
advice or clarity orunderstanding or you know, to
answer my questions so I couldreally start to understand how
this works, so we could get ahandle on it, and it ended up
saving, like I don't know, 50plus I don't know how much
thousands of dollars.
(03:59):
That I saved by understandinghow it worked, because it wasn't
being done, even though the CPAwas doing the taxes for us
right, like the data that wegive them also matters, and so
the way that the data was beingpresented wasn't done in the
correct fashion.
So I say that to say you canpay for advice in order to
(04:20):
increase your you know,knowledge and expertise, because
it's been my experience.
What we don't know and thenwhen we outsource, that can end
up costing us more than weoriginally imagined in time and
money.
Because when we aren't aware ofthe time involved for that
other person and they're justtelling us it takes X, y, z time
(04:41):
, but we haven't done itourselves, how do we know that?
That's true.
So if a bookkeeper quotes youyou 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 numberis high or low.
Yes, you can ask your businessbesties and colleagues, but when
you've done it yourself, youknow the time involved, and I
(05:04):
always want to say that.
Make sure you understand that Iam 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 outsourcethem.
If you're unsure of what to askwhen hiring a bookkeeper, here
are, I think, the five reallygood questions to ask them.
Number one what experience doyou have working with businesses
(05:27):
like mine?
This is the same question thatI talked about on the CPA
podcast.
Like what would you ask yourCPA?
Because every business isdifferent and definitely, I
believe, brick and mortarbusinesses are different than
online businesses.
So most of my clients haveonline businesses and I've
noticed that most accountingsoftware is more for brick and
mortar businesses.
(05:47):
So you want to make sure thatyour bookkeeper understands the
online business space, becauseif 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 makesure that they work with online
businesses.
If you are an online business,every industry has different
financial needs, so you want abookkeeper who understands the
(06:09):
specific challenges and cashflowpatterns of your type of
business.
Number two is what software dothey use and do they have
experience with the one thatyou're using?
If you already use QuickBooks Iknow Xero is another one or
maybe another platform just makesure that they're familiar with
it.
I've seen some people useFreshBooks.
(06:31):
I'm not familiar with that.
Like I said, I grew up on.
You know over the last what 15years I've been using QuickBooks
.
I know it.
I'm not gonna learn a differentsoftware system.
Most accountants want and, likeyou know, quickbooks reports,
so that's what I've decided tokeep with.
So just make sure that they'regoing to use the same one as
(06:54):
your accountant.
Or, if they don't ask youraccountant, are you okay with
that?
Because the last thing that youwant to do is have software
that the bookkeeper uses andthen the accountant might charge
extra because the systems maybeisn't either easily
transferable to them or they'renot as familiar with it or
(07:17):
looking at that.
So I always ask the CPA like,what is the software program
that they use?
And most of the times it'sQuickBooks.
So just making sure and mostbookkeepers use QuickBooks, but
just making sure that you'rekind of all on the same page.
Number three is how often willwe communicate and what reports
are you going to provide?
You know some bookkeepers domonthly reports.
(07:39):
Some offer weekly updates.
Some I have heard through thegrapevine of other bookkeepers
that I've worked with don't domonthly reports.
And if that's someone thatyou're interviewing, I would say
run, because at a minimum youwant monthly reports so you can
see where you are.
Clarity comes with your numbersand in real time you know if
(08:01):
you are pulling reports forthree months ago, that's, that's
long gone, right.
So clarify what kind ofinsights you're going to get and
how accessible that they willbe.
Are you going to get just a Pand L and a balance sheet?
Are you going to get an AR andAP report?
What are the reports thatthey're willing to give so you
have a clear picture of whereyou stand financially?
(08:23):
Number four is what's includedin your services and what would
be an additional cost.
Some bookkeepers only trackexpenses.
Others will help with theinvoicing, payroll If you're at
that stage tax prep just makingsure you know what's covered, so
there are no surprises.
You know, does the bookkeepertalk to your accountant for you
(08:44):
or are you the go between?
And I do think you need to beinvolved 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 theirrole?
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 hiresomeone.
And then the fifth one is how doyou ensure accuracy and
(09:05):
security with your financialdata?
Your bookkeeper is going tohave access to your sensitive
financial information.
So ask them how are they goingto protect your data and what
systems do they have in place toprevent errors?
And I have a bonus one for you.
Number six is how often do theygo on vacation and who takes
care of you when they're gone?
(09:26):
So if they are someone wholikes to travel a lot and they
are out, what happens if youhave questions?
How are you going to get aholdof them?
Do they have backup teammembers?
Are they big enough where theykind of have a firm, or is it
just a one man, you know, onewoman show?
Like, what is their process forwhen they aren't working?
(09:49):
Okay, so to recap, six ones Iwould think about and ask what
experience do they have workingwith businesses like yours and
get them to start talking andjust to share with you.
That way you will be.
I think through the sharingyou'll be able to create more
questions.
Number two what software dothey use, and do you have
experience with the one that Iuse?
Number three how often willthey communicate and what way
(10:13):
will they communicate?
So if they only want to talkvia email and they charge extra
for phone, okay, what is thatcost?
And what reports are they goingto provide on a monthly basis
that are included in that fee?
Number four is what is includedin the services and what would
be an additional cost?
Five how do you ensure accuracyand security with financial
(10:35):
data?
And then my bonus one is ifthey go on vacation, who is
their backup person?
Who takes care of you whenthey're gone?
What does that look like?
You know, having the correctbookkeeper for you can make
managing your finances so mucheasier.
Right, and hiring the wrong onecan cause a lot of stress.
I've had several bookkeepersfriends that have gotten clients
(10:57):
from other bookkeepers thatsaid they were doing what they
were supposed to do and theyweren't.
So just really be very clear,very make them be very
transparent as to what you wantwhat you expect, so that you
don't find out the hard way,right With time and or money,
that you're not getting what youpaid for.
So that's what I've got for youtoday.
(11:17):
If you want more tips onmanaging your business finances
with confidence, being with yourmoney, having more fun with it,
I would love for you to join myfree Facebook community Money
Mindset Tips for Women inBusiness.
You can join with the link inthe show notes or you can just
go to Facebook and search MoneyMindset Tips for Women in
(11:37):
Business.
Okay, thanks for being here.
I'll see you in the nextepisode.
Did you learn something today?
Do you know another femaleentrepreneur who might be
avoiding her money?
Will you send this episode overto her for me and, if you have
it in you, please leave me areview for this podcast.
It helps the show grow and Ilove hearing from you.
(11:57):
See you next week.
On today's podcast, we're going to be talking about
hiring a bookkeeper,specifically, the five essential
questions I think you need tobe asking before bringing
someone onto your team.
Whether you're hiring yourfirst bookkeeper or you're
looking to switch to someone new.
These questions are going tohelp you be able to find the
right fit for you.
Do you want to create a systemto stop avoiding your money?
(00:20):
Maybe you're feeling guilt andshame when it comes to finances.
Welcome to your Money, yourRules.
I'm Erin, a former certifiedfinancial planner and CFO, and
yet I used to avoid my money andhad fear, no matter how much we
had.
I can't wait to teach you how Iovercame my money avoidance and
started consistently managingmy finances in a really simple
(00:42):
way.
It's time to get comfortablewith money.
Before we dive into this week'sepisode, I want to invite you
to join me for a one-on-onemaster your money coaching
session.
During this hour, we'll worktogether to create a tailored
plan that helps you align yourfinances with your unique goals,
energy and mindset.
If you're ready to transformyour relationship with money and
(01:03):
create the freedom andabundance you deserve, head over
to my website,generatealifewelllivedcom and
schedule your session.
So let's talk all thingsbookkeeper.
To be completely transparent, Istill do my own books.
I learned the hard way withQuickBooks on what's called
QuickBooks Enterprise.
It's a desktop edition which isfor construction, and it might
(01:26):
be some of the toughest softwareto understand.
And yet, because I always loveto talk about how we learn
through obstacles, I am sograteful that I learned on some
of the hard stuff, because nowI'm able to look at clients'
reports in such a minimal amountof time, because I spent 10
years doing it in my family'sconstruction business.
(01:47):
I mean, I can only imagine theoverwhelm that some of you might
be feeling trying to learn thelanguage of QuickBooks or trying
to read reports, and so I wantto dive into.
You know a bookkeeper isn't justsomeone like that tracks your
numbers to.
You know a bookkeeper isn'tjust someone like that tracks
your numbers.
There's someone that you'regoing to trust with your
(02:08):
financial data and someone who'sgoing to help you.
I view everyone on your team assomeone that's helping you get
to where you want to go, and soasking the right questions
upfront, I think, is going tosave you so many headaches later
.
And this might sound like I'mtalking out of both sides of my
(02:31):
ass, so bear with me here.
On the one hand, I totallythink that you should know how
to do QuickBooks and howQuickBooks works, because the
more you know, the better you'reable to converse with your
bookkeeper and your CPA Likeyou're speaking the same
language're able to conversewith your bookkeeper and your
CPA Like you're speaking thesame language as them.
(02:51):
And then, on the flip side ofthat, I also get that it's like
a foreign language and thatspending time learning it can
feel very overwhelming andcumbersome.
So, for those of you that feelthis way, I just want you to
ponder taking some courses,watching some YouTube videos,
asking your local you can evenask your local SBA community.
They typically have classes ata lower cost that you can pay
for Um, or you can even pay yourbookkeeper for some upper level
(03:16):
training.
I know that when I was trying tounderstand in Texas, we have
something that's calledfranchise tax, which is above
and beyond federal taxes orstate taxes, and when I came
into the business, I thoughtwhen I started diving into
franchise tax, I thought that wewere totally overpaying which
we were and so I really starteddiving in to it.
(03:38):
I taught a lot of it myself,but then I would pay the CPA for
advice or clarity orunderstanding or you know, to
answer my questions so I couldreally start to understand how
this works, so we could get ahandle on it, and it ended up
saving, like I don't know, 50plus I don't know how much
thousands of dollars.
(03:59):
That I saved by understandinghow it worked, because it wasn't
being done, even though the CPAwas doing the taxes for us
right, like the data that wegive them also matters, and so
the way that the data was beingpresented wasn't done in the
correct fashion.
So I say that to say you canpay for advice in order to
(04:20):
increase your you know,knowledge and expertise, because
it's been my experience.
What we don't know and thenwhen we outsource, that can end
up costing us more than weoriginally imagined in time and
money.
Because when we aren't aware ofthe time involved for that
other person and they're justtelling us it takes X, y, z time
(04:41):
, but we haven't done itourselves, how do we know that?
That's true.
So if a bookkeeper quotes youyou 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 numberis high or low.
Yes, you can ask your businessbesties and colleagues, but when
you've done it yourself, youknow the time involved, and I
(05:04):
always want to say that.
Make sure you understand that Iam 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 outsourcethem.
If you're unsure of what to askwhen hiring a bookkeeper, here
are, I think, the five reallygood questions to ask them.
Number one what experience doyou have working with businesses
(05:27):
like mine?
This is the same question thatI talked about on the CPA
podcast.
Like what would you ask yourCPA?
Because every business isdifferent and definitely, I
believe, brick and mortarbusinesses are different than
online businesses.
So most of my clients haveonline businesses and I've
noticed that most accountingsoftware is more for brick and
mortar businesses.
(05:47):
So you want to make sure thatyour bookkeeper understands the
online business space, becauseif 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 makesure that they work with online
businesses.
If you are an online business,every industry has different
financial needs, so you want abookkeeper who understands the
(06:09):
specific challenges and cashflowpatterns of your type of
business.
Number two is what software dothey use and do they have
experience with the one thatyou're using?
If you already use QuickBooks Iknow Xero is another one or
maybe another platform just makesure that they're familiar with
it.
I've seen some people useFreshBooks.
(06:31):
I'm not familiar with that.
Like I said, I grew up on.
You know over the last what 15years I've been using QuickBooks
.
I know it.
I'm not gonna learn a differentsoftware system.
Most accountants want and, likeyou know, quickbooks reports,
so that's what I've decided tokeep with.
So just make sure that they'regoing to use the same one as
(06:54):
your accountant.
Or, if they don't ask youraccountant, are you okay with
that?
Because the last thing that youwant to do is have software
that the bookkeeper uses andthen the accountant might charge
extra because the systems maybeisn't either easily
transferable to them or they'renot as familiar with it or
(07:17):
looking at that.
So I always ask the CPA like,what is the software program
that they use?
And most of the times it'sQuickBooks.
So just making sure and mostbookkeepers use QuickBooks, but
just making sure that you'rekind of all on the same page.
Number three is how often willwe communicate and what reports
are you going to provide?
You know some bookkeepers domonthly reports.
(07:39):
Some offer weekly updates.
Some I have heard through thegrapevine of other bookkeepers
that I've worked with don't domonthly reports.
And if that's someone thatyou're interviewing, I would say
run, because at a minimum youwant monthly reports so you can
see where you are.
Clarity comes with your numbersand in real time you know if
(08:01):
you are pulling reports forthree months ago, that's, that's
long gone, right.
So clarify what kind ofinsights you're going to get and
how accessible that they willbe.
Are you going to get just a Pand L and a balance sheet?
Are you going to get an AR andAP report?
What are the reports thatthey're willing to give so you
have a clear picture of whereyou stand financially?
(08:23):
Number four is what's includedin your services and what would
be an additional cost.
Some bookkeepers only trackexpenses.
Others will help with theinvoicing, payroll If you're at
that stage tax prep just makingsure you know what's covered, so
there are no surprises.
You know, does the bookkeepertalk to your accountant for you
(08:44):
or are you the go between?
And I do think you need to beinvolved 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 theirrole?
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 hiresomeone.
And then the fifth one is how doyou ensure accuracy and
(09:05):
security with your financialdata?
Your bookkeeper is going tohave access to your sensitive
financial information.
So ask them how are they goingto protect your data and what
systems do they have in place toprevent errors?
And I have a bonus one for you.
Number six is how often do theygo on vacation and who takes
care of you when they're gone?
(09:26):
So if they are someone wholikes to travel a lot and they
are out, what happens if youhave questions?
How are you going to get aholdof them?
Do they have backup teammembers?
Are they big enough where theykind of have a firm, or is it
just a one man, you know, onewoman show?
Like, what is their process forwhen they aren't working?
(09:49):
Okay, so to recap, six ones Iwould think about and ask what
experience do they have workingwith businesses like yours and
get them to start talking andjust to share with you.
That way you will be.
I think through the sharingyou'll be able to create more
questions.
Number two what software dothey use, and do you have
experience with the one that Iuse?
Number three how often willthey communicate and what way
(10:13):
will they communicate?
So if they only want to talkvia email and they charge extra
for phone, okay, what is thatcost?
And what reports are they goingto provide on a monthly basis
that are included in that fee?
Number four is what is includedin the services and what would
be an additional cost?
Five how do you ensure accuracyand security with financial
(10:35):
data?
And then my bonus one is ifthey go on vacation, who is
their backup person?
Who takes care of you whenthey're gone?
What does that look like?
You know, having the correctbookkeeper for you can make
managing your finances so mucheasier.
Right, and hiring the wrong onecan cause a lot of stress.
I've had several bookkeepersfriends that have gotten clients
(10:57):
from other bookkeepers thatsaid they were doing what they
were supposed to do and theyweren't.
So just really be very clear,very make them be very
transparent as to what you wantwhat you expect, so that you
don't find out the hard way,right With time and or money,
that you're not getting what youpaid for.
So that's what I've got for youtoday.
(11:17):
If you want more tips onmanaging your business finances
with confidence, being with yourmoney, having more fun with it,
I would love for you to join myfree Facebook community Money
Mindset Tips for Women inBusiness.
You can join with the link inthe show notes or you can just
go to Facebook and search MoneyMindset Tips for Women in
(11:37):
Business.
Okay, thanks for being here.
I'll see you in the nextepisode.
Did you learn something today?
Do you know another femaleentrepreneur who might be
avoiding her money?
Will you send this episode overto her for me and, if you have
it in you, please leave me areview for this podcast.
It helps the show grow and Ilove hearing from you.
(11:57):
See you next week.
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