Stop Hiring in Chaos: How to Delegate Successfully

If you’ve ever hired someone to lighten your load and still felt like you were doing everything yourself, this episode is for you!

Entrepreneurs are often told, “Just hire help,” but what no one tells you is how to prepare your business to receive that help in a way that actually works. Without structure, even the most capable virtual assistant can’t succeed. 

And without clarity, you’ll find yourself stuck in the same cycle: repeating tasks, chasing updates, and wondering why things still feel so heavy.

So today, I’m pulling back the curtain on what really causes delegation to fail and it’s probably not what you think. It’s not about who you hired. It’s about what you dropped them into.

You’ll hear how my client went from swearing off VAs altogether to creating a structured plan to bring on the right support with confidence. All because she took the time to prepare her backend with intention instead of rushing into another chaotic handoff.

What we cover today:

2:43 – What a messy backend taught me about why delegation keeps breaking down

4:23 – Why hiring help without systems just creates more stress

5:41 – How the Back Office POWER Checklist shows you what’s really slowing you down

6:56 – What changed when Carla 2.0 stopped hiring from burnout and started preparing with intention

8:00 – How a clear plan made Carla confident about hiring again

10:02 – The mindset shifts that make delegation work and give you your time back 

Resources Mentioned:

📋 Grab the Back Office POWER Checklist, a fillable Google Doc that will help you  quickly audit your back office, spot inefficiencies, and create a smoother, more efficient operations one system at a time!

Let me know your thoughts! Click here to send me a text.

Tired of feeling stuck behind the scenes?

Book a POWER In Motion Jumpstart Session! A 60-minute call where we’ll pinpoint what’s holding you back and build a 30-day action plan you can use right away.

It’s the perfect first step before joining the Founders Circle.  Book your session here.

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Episode Transcript

Speaker 1 (00:00):
If you've ever hired someone to help relieve the
overwhelm you feel in yourbusiness and you still feel like
you're doing everythingyourself, this episode is for
you, because I'm going to betalking about why you keep
failing at delegation.
And spoiler alert, it'sprobably not the reason you
think.
It's not about who you hired.

(00:20):
It's about what you hired theminto.
Whether you're the CEO tryingto grow your business or you're
just trying to get control ofyour time or get time back, your
systems matter and delegationisn't the problem, but your back
end might be.
So let's talk about it.
Welcome to the Mind your Timepodcast.

(00:41):
I'm Shannon Baker, your coffeeloving host and business
operations strategist.
If your business feels chaoticand you're tired of spinning
your wheels, you're in the rightplace.
Each episode contains boldstrategies and practical
insights rooted in my power andmotion framework to help you
streamline your operations,reclaim your time and grow
without burnout.
So, whether you're juststarting out or scaling the six

(01:02):
figures and beyond, I'll helpyou simplify, set boundaries and
build a business that works foryou.
So grab a cup of coffee or yourfavorite beverage and let's
dive in.
Okay, so let me start by takingyou back to one of the first
clients that I ever worked withas a virtual assistant.
We're going to call her Melissa.
Now, on the outside, everythingin her business looked amazing.

(01:24):
She was almost making sixfigures, she was booking
speaking gigs and she had awaitlist full of dream clients.
But once I got to look behindthe curtains and see the real
deal, her business was a mess.
There were no SOPs, there wasno task management system,
nothing was documented, it wasjust pure chaos.

(01:47):
Now, during her discovery call,I noticed some red flags that I
should not have ignored.
She was very vague about howshe worked and she couldn't
explain her processes.
Actually, she was prettyscattered, but I ignored all of
those red flags because I wasnew and I just really believed

(02:12):
that I could help her.
Well, guess what?
I couldn't.
Every time I tried to createstructure in Melissa's business,
she just got frustrated.
Melissa's business she just gotfrustrated, flustered or she
just plain out ghosted me.
One day she even said that Iwas giving her too much work,

(02:38):
when all I was doing was tryingto introduce a little clarity
and help her get organized.
Needless to say, I ended upfiring her as a client, but that
was the moment that I realizeddelegation isn't always the
issue Nine times out of 10, it'sthe back end of the business.
I remember sitting at my deskthinking, is it me, am I asking

(02:59):
for too much?
But deep down I know I wasn't.
I was asking just for basicthings clarity, communication
and structure.
And that's when it hit me.
It wasn't about my effort, itwas really about her readiness.

(03:20):
And that moment has stuck withme ever since because I've seen
it happen time and time again,especially with women who are
purpose-driven and reallyfocused on reaching their goals
in their business.
So let's really talk about thisNow.
If you're anything like myclient Carla now, this is

(03:42):
another client then you'reprobably thinking delegation
just doesn't work for you either.
You've handed off a few tasksevery now and then.
Maybe you've even hired a VAonce, twice or three times, and
each time you failed.
But somehow it always ends upthe same.

(04:04):
Things start slipping throughthe cracks, you find yourself
repeating your instructions andyou get frustrated.
So you just end up doingwhatever it is yourself.
So you tell yourself it'seasier if you just handle it.
But let me tell you what'sactually happening.
You aren't failing atdelegating You're not but you're

(04:26):
delegating into eitherdisorganized or non-existing
systems.
So let's say you hire someoneand say, well, just help me,
jump in wherever I need support.
Does that make sense?
No, it doesn't.
But that's what you've beendoing.
Without clear expectations,documented steps or a system a

(04:50):
person can plug into, they areleft guessing, and guesswork
leads to mistakes, mistakes,create mistrust and the next
thing you know you're right backwhere you started Stressed out,
burned out and alone in theweeds.
So the problem isn't that youhired the wrong person.

(05:13):
It's that your back end wasn'tready to support them so they
could support you.
Now I need you to hear me out,because this doesn't mean that
I'm telling you to go create a200-page SOP manual overnight,
but you do need a system.
That's a foundation that givesyour support, clarity, direction

(05:36):
in a documented way so they canactually help you.
And that's where the backoffice checklist comes in.
It's the very first thing Igive anyone who is preparing to
hire or who's had a poorexperience with hiring in the
past.
It helps you honestly look atwhat's working, what's missing

(05:57):
and what's creating bottlenecksin your business behind the
scenes, because if your businessis built on adrenaline and last
minute decisions, no virtualassistant in the world can keep
up with that.
But if you give them a roadmap,give them the big picture and
give them breathing room to workwithin your existing systems,

(06:18):
they can help you lead.
That's exactly what another oneof my clients that we're gonna
call Carla 2.0 did.
She came to me completely overthe whole hiring building a team
thing.
She'd already written offhiring another virtual assistant
because she had failed at it afew times.
She said it didn't work and itwas more stress than support.

(06:41):
But during her power in motionjumpstart session we took a
different approach.
Instead of rushing to fill inthe gaps in her back office, we
slowed things down and got clearon what she actually needed
behind the scenes.
So we started with completingthe back office power checklist
and we did it together.
That changed everything.

(07:04):
She could see exactly where hersystems were fuzzy, where
handoff points were breakingdown and where her expectations
had been living only in her head.
This gave Carla 2.0 a whole newlevel of clarity, not just on
what wasn't working but on whatshe needed to have in place

(07:26):
before anyone else was boughtinto the business.
By the end of her session shedidn't feel that she was quite
ready to hire yet, but she feltequipped to do it differently.
The next time she decided to tryagain.
She had a starting point, a30-day focus, a way to prepare

(07:47):
for the kind of support sheactually wanted and needed.
And for the first time shewasn't hiring from the verge of
burnout, she was hiring withintention.
Now her plan is to bring on aVA who can truly grow with her,
and when she does, she alreadyknows what the onboarding

(08:08):
process will look like for hervirtual assistant, because we
mapped it out together.
She's also planning to enrollthem into Founder Circle once
they work together for at least90 days so that the virtual
assistant can be more familiarwith her business, and then
they're going to complete thedelegate with confidence guide
so they can build out herbackend end together and she

(08:31):
will no longer be the bottleneckin the process.
What a difference preparationmakes.
And it started with one honestlook at what was happening
behind the scenes in herbusiness.
That's what I want for you.
So let me ask you do you knowwhat kind of support you
actually need, or are you hopingyou can hire someone that will

(08:56):
just figure it out for you?
Do you have a repeatable way tohand things off, or are you
winging it every time somethingcomes up, answer those questions
honestly.
So here's your quick winchallenge for this week.

(09:17):
I want you to download the backoffice power checklist and
complete it honestly.
A link to it is in the shownotes and I don't want you to
sugarcoat it.
Don't skip over things, becausethey kind of work and if it's
not efficient, it's slowing youdown or making delegation harder
then it's time to address itand fix it.

(09:39):
This will give you a realstarting point and I'm not just
talking about for hiring, butit's the starting point for
building a business that canactually support the growth you
want.
Now let's wrap this up with afew key mindset shifts that are
gonna change how you approachdelegation for good.

(10:01):
First of all, hiring someone isnot the fix, but getting
yourself and your businessprepared is.
So if your backend is chaotic,it's not gonna matter who you
bring in, you're going to havethe same problem.
So you have to make space forthem to be able to succeed by

(10:23):
creating systems before you hire.
We also talked about the factthat delegation works when you
lead it well.
So that doesn't mean youmicromanage the person.
It means you give your teamstructure systems those will
give them the context that theyneed to step into their role and

(10:45):
support you with confidence.
The third thing we talked aboutis you don't need to do a
massive overhaul of yourbusiness to get results.
Sometimes, the change that youneed is very simple.
It may only take one focusedaudit or a clear 30-day plan to

(11:08):
help you shift the wayeverything works in your
business, just like Carla 2.0did.
Now, if you're ready to finallyget support that sticks, then
the back office power checklistis your next step.
It's a great place to start,and so many women that I work
with they avoid this stepbecause it feels like it's

(11:31):
slowing them down.
But slowing down to assess theback end of your business
accurately, it's not a setback.
It's what makes scalingpossible.
Skipping this step that is whatkeeps you stuck.
But if you want morepersonalized support as you

(11:53):
complete the checklist, I wouldlove for you to book a Power in
Motion Jumpstart session with me.
In just one hour we will createa 30-day action plan that gets
your back in organized andprepares you to hire the right
person the right way, so you canfinally get out of the weeds

(12:14):
and into the role you are meantto lead from Again.
You can grab that checklistfrom the link in the show notes,
or you can also click the linkand book that power in motion
jumpstart session with me.
One thing I want you to rememberis you don't need to do more to
make your business run better.

(12:35):
You just need the rightfoundation.
So let's build it together.
Thanks for hanging out with methis week.
If you've made it this far,it's clear you're ready to shake
things up and take control ofyour business, and I'm here for
it.
But remember, just listening tothis episode won't get you
better results.
I challenge you to break themold and take action today.

(12:57):
Your next move let's connect,head to the show notes and book
a call with me to learn how theMighty Society membership can
help you streamline your backoffice and reclaim your time.
If you're not ready for thatstep yet, no worries.
Connect with me on Instagram atthe underscore Shannon Baker,
and tell me what resonated mostfrom today's episode.

(13:18):
And if you're loving thepodcast, leaving a review is a
quick way to show your supportand help more entrepreneurs like
you break free from the chaos.
Listening is great, but actioncreates transformation.
Go, make it happen and untilnext time, keep calm and
streamline.