February 11, 2025 • 12 mins
Ever finish a project, pat yourself on the back for a job well done, and then… nothing? No follow-up, no repeat work, just radio silence. You know they liked your work—so why aren’t they coming back? The answer has nothing to do with talent and everything to do with positioning. In this episode, Jamie and I share how to go from “task-completer” to “strategic partner”—and why that’s the key to locking in long-term clients.
WE ALSO TALKED ABOUT
• Why doing great work isn’t enough to get repeat business
• The key shift from “task-completer” to “strategic partner” (and why it changes everything)
• The role of messaging and positioning in attracting ongoing work
• How to lead clients toward their next project before they even realize they need it
• Why retainer agreements work—and how to get clients to want one
• The power of prequalifying your clients so you’re only working with people who see your value
• How small language shifts—like using “partner” instead of “hire”—change client perception
• Why being the person who “solves problems” (not just “delivers work”) makes you indispensable
• An analogy that will forever change how you think about client work
About Our Guest
Jamie Brindle been freelancing for 16 years, and in that time he's worked with clients ranging from local mom and pop restaurants, to Fortune 500 companies like Google, Hillshire, Netflix, and Lionsgate. In 2020 he began producing social media content for his fellow freelancers on TikTok, Instagram, YouTube, an LinkedIn. Today he helps over 500,000 freelancers everyday with practical tips.
Links You Might Want
Jamie's Newsletter
Connect with Jamie on
LinkedIn
Thank you for taking time out of your busy day to listen to Boss Responses. This podcast is a passion project that comes from years of helping freelancers shape a business that supports the lifestyle they want.
Have a question you'd like answered? Send it to info@bossresponses.com
If you'd like to support the podcast, click that link above. Those lattes help keep us going and are much appreciated!
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Treasa Edmond (00:00):
Welcome back to the Boss Responses podcast.
Today's episode is all aboutturning those one-off gigs into
long-term client relationships.
I know this is a big topic thatI've been hearing more about
lately.
I hope our discussion todayreally helps you.
If you're dealing with thisissue as well, let's get into it
.
If you're a freelancer,business owner or anyone who
(00:25):
deals with clients, you're inthe right place.
I'm your host, teresa Edmond.
I've been dealing with clientsand running my business for
nearly two decades and in thattime I've dealt with my share of
doubt, imposter syndrome andnot knowing what to say when a
client asked a question I wasn'tready for.
I created this podcast toempower you with the boss
(00:46):
responses you need to grow yourbusiness.
Each week, my guest co-host andI will bring you five episodes
packed with practical insights.
Monday through Thursday, weanswer your questions, and
Fridays, we dive deep to explorehow our co-hosts embrace their
role as the boss of theirbusiness.
Welcome to Boss Responses.
(01:08):
We are back for day two withJamie.
Jamie, what's the question fortoday?
Jamie Brindle (01:15):
All right, trace you ready for this one?
Yep, this is coming from Jen inDenver, colorado.
Jen says I've been freelancingfor about three years and I do
well with one-off projects, butI really want more long-term
clients.
I find that even when clientsare happy with my work, they
don't always come back.
What's the best way to turnshort-term gigs into ongoing
(01:38):
work?
Treasa Edmond (01:40):
I love this question.
You need to become a strategicpartner with your clients,
rather than a task completer.
If you are just completingtasks, they will have you
complete the task and then theymove on with their lives.
And we have to realize ourclients are busy people In the
corporate world.
They're stuck in meetings forlike seven of the eight hours a
(02:01):
day.
It's horrific for the poorin-house people and I'm sorry
for them, but we don't have todo that.
We focus on one client at a time.
To us it seems like we've donea really good job on this thing.
We've put in a lot of time.
We focused entirely on theirproject.
To them it's like I gave theman assignment.
They did it.
Now I can move on to the nextassignment and you might not be
(02:21):
the right person for that.
If you become a strategicpartner and you make yourself
valuable and you ask them theright questions that gets them
asking questions in-house, whichraises their stock in-house
you're going to be the firstperson they think of every time
they're going to say we havethis new project.
(02:42):
I'd really like to get Jen'sinsights on this before we
formulate everything, or we'dreally like to bring Jen in to
help us develop the brief onthis project so that we can make
sure we're hitting it right.
So you're providing a littlebit more strategy work and in
the process, you're getting paidmore, and then you're also
getting paid for the actualproject that you're completing.
(03:05):
I think that's about the onlyway to do it.
The other thing is to offerongoing retainers, and I still
do that by showing value.
This is what my clients getwhen they work with me.
As a retainer client, I becomemore familiar with your brand.
I require less oversight.
I turn in well-edited,ready-to-go turnkey content
(03:27):
every single time.
So you need to talk about theproblems you're solving for your
clients and the value you'rebringing, instead of just saying
I write blog posts.
So it's a messaging thing, it'sa marketing thing and it's
solving problems for yourclients.
If you want to go into thestrategy work, then that's one
way to do it.
If you want to do deeperconsulting work, that's
(03:50):
definitely, I think, thestrongest way to do it, but you
can also do it by formingrelationships with your clients,
letting them know from the getgo I work with all of my clients
long term, because this is whatyou get in return with all of
my clients long term becausethis is what you get in return.
And then they go into itthinking, ok, I don't need to
(04:10):
hire five writers, I only needtwo or three, because she's
going to take on the work of theothers and do it really well.
And then gradually you becometheir go to person for the more
important projects.
But how do you approach this,jimmy?
Jamie Brindle (04:24):
for the more important projects.
But how do you approach this,jimmy?
Yeah, no, I think all of thatis spot on.
Here's the thing the lifetimevalue of a client, optimizing
for repeat business this stuffis foundational to a successful
freelance business.
Yeah, so it is something thatyou need to figure out, because
what a waste if you go to allthe effort of acquiring a client
, of doing the marketing, doingthe advertising, doing the sales
(04:47):
, earning the trust.
You go to all that effort tojust do one project with them.
It's a waste of effort, if youask me.
Treasa Edmond (04:54):
I think so too.
Jamie Brindle (04:55):
It's optimizing for.
Okay, after that project.
How do I because, as youmentioned, they're busy, they're
not thinking about how do Ikeep Teresa employed?
How do I keep bringing her morestuff?
How do I keep bringing Jamiemore stuff?
It's incumbent on thefreelancer to say okay, after
that initial project.
How do I take them by the handand walk them to the next
project?
(05:15):
And then how do I take them bythe hand again and walk them to
the next thing?
This stuff needs to hire meagain, and they might.
But it might be eight and ahalf months from now when they
remember that they've got you inthe pocket.
(05:37):
You need to continue holdingonto that mantle of strategic
partner and bring them newsolutions to problems or say,
hey, usually, as you're handingthem the deliverable for the
first project, say usually oncesomebody's done this or once
somebody's got this in hand.
These are the next four thingsthat they're solving for, and
(06:03):
that's what I've seen in mybusiness.
And what do you think aboutthese four?
Are you coming up against anyof these?
It's like oh well, that one,well, great, I'm going to pull
this solution out of the folder.
Then here you go and we'removing on to the next one.
Treasa Edmond (06:10):
Yeah.
Jamie Brindle (06:11):
So it is.
It's really about designing theprocess of yes.
I mean, it's important to knowhow to make someone turn someone
from a stranger into a lead,into a client, and that's what a
lot of the content on theinternet is about and that's
what a lot of freelancers aresolving for.
But there's this fourth stepover here.
That's, I would argue, the mostimportant, which is how to take
(06:31):
them from a client to alifetime client.
If you can optimize for that,if you can build your business
on that concept, I think you'regoing to be in pretty good shape
.
Treasa Edmond (06:42):
And that's one of the main premises.
What's the right word there?
Jamie Brindle (06:46):
I think I was an English major and I should know
the answer.
But I'm going to go withpremises.
Treasa Edmond (06:51):
That's one of the main premises.
We're going to just stick withthat.
That's one of the main premisesof this podcast is, well, it's
two things that Jamie said.
One you're not just doing gigs,you're a freelancer running a
business.
Even if you think you're notrunning a business, you are, and
(07:12):
if you don't embrace that, thenit's never going to work.
It's just never going to workout the way you want it to.
If it does, it's accidental andthen it's not sustainable.
So you really do need to runyour business like a business,
which means planning, havingprocesses, all of that.
The other thing turning thoseclients into lifetime clients I
call that client management andit's something that I'm pretty
(07:32):
passionate about.
When we and this is a mindsetthing, it's also a wording thing
.
So Jamie used the word hiringand I said this on the podcast
before.
I never say my clients hire mebecause I'm not doing a job for
them.
When I'm talking to my clients,I use partnership language from
the very first communication.
That means if we choose to workon this project together, this
(07:55):
is what will happen.
So I talk partnership languageacross the way.
I never say hiring, I never sayjob, there are just certain
words I've mixed from myvocabulary when I'm dealing with
clients.
And it makes a huge differencein how they perceive me and that
and I take control of ourworking relationship not them,
(08:17):
but of our working relationshipfrom our very first
communication.
So I ask those pre-qualifyingquestions.
When they come on the discoverycall because they've met the
threshold for the pre-qualifyingquestions, I say thank you so
much for coming on this call.
I'm really excited to talkabout your project today.
This is what the call is goingto look like.
I'm going to ask you a seriesof questions so I can find out
(08:39):
more about what you want toaccomplish, who your audience is
, whatever the questions will be, and then I say and then at the
end I will take any questionsyou have and tell you a little
bit about my process.
Does that sound okay?
So they let you ask thequestions and then, by the time
they get to where they can askyou questions, you have already
asked insightful, strategicquestions about their project
(09:01):
and found out information theywouldn't have thought to include
.
So they see you as the expert.
They're ready to follow yourlead.
That means you get to be theexpert in the business
relationship and they get thefreedom to be the expert doing
what they do.
Jamie Brindle (09:14):
Absolutely.
Treasa Edmond (09:15):
It just makes it a more fulfilling relationship
across the board, full of mutualrespect.
That's how you turn them into alifetime client.
You lead them by the hand.
You make it so, so easy to workwith you not for you or you for
them.
You make it so much easier towork with you, to partner with
you, and I think it's a veryslight shift, but when you make
(09:38):
that, it changes everything inhow your clients treat you.
Jamie Brindle (09:42):
Absolutely.
Yeah, it is.
I think a lot of folks maybebecause they're coming from the
nine to five world or justbecause that's what's most
represented in culture what haveyou?
A lot of people think ofthemselves as a product on the
shelf as opposed to a strategicpartner.
A lot of people assume that theclient knows what they want and
(10:05):
that the client's got a plan,and that the client knows how
much it's going to cost to dothis.
And all of that is fallacious.
It's literally the client isrenting your expertise.
Treasa Edmond (10:15):
Yeah, that's the starting point.
That's all it is At the end ofthe day.
Jamie Brindle (10:18):
Yeah, you're coming in and there's going to
be a big sigh of relief if youestablish yourself as the expert
here.
It's not all right.
We're on this call.
What do you guys want from me?
What do you want me to do foryou?
That's not it.
They want you to tell thembecause you're the one that
spends your working hours inthis space.
If they knew what needed to bedone here, they wouldn't need
(10:40):
you.
So it's about assertingyourself as that expert and not
thinking of yourself as aproduct of the shelf, for sure.
Treasa Edmond (10:45):
Yeah, one of my favorite examples to use in a
situation like this, when we'retalking about giving the client
what they need instead of whatthey think they need, and then
establishing yourself as anexpert, becoming a street to
geek partner, all of thosethings.
It's very similar to thepricing issue from yesterday.
You can be low priced andthey're going to see you as a
low priced writer.
(11:07):
If you are a higher pricedwriter, they're going to say
that there's more perceivedvalue.
Well, in a situation like this,let's say my water heater won't
stay lit, because this happenedto me recently.
If my water heater won't staylit because this happened to me
recently If I call a plumber andsay my water heater won't stay
lit, I think I need a new pilotlight, and they just come out
and change the pilot light.
They're not a good plumber.
Exactly, they're not good atwhat they do.
(11:28):
If I say my water heater won'tstay lit, I think it might be
the pilot light.
They might say what's the modelnumber?
And I'll make sure I bring theright one with me in case that's
what it is.
But I'm going to have to dosome diagnostics to make sure
I'm solving the right problemand then they do all of the
things, I pay the very hefty fee.
My water heater now stays litbecause, by the way, it wasn't
(11:48):
the pilot light and then we itwas some random thing and he did
try changing the pilot lightand it didn't solve the problem
because he had to troubleshoot.
So, yeah, it's a matter ofshowing what the client needs,
because you have paid enoughattention to the situation and
you're not just giving them whatthey think they need, which is
(12:11):
only ever a partial solution.
Jamie Brindle (12:14):
Exactly, exactly.
Treasa Edmond (12:16):
Yeah, I love this question.
I love this question.
Thanks, jen.
All right, come back for daythree tomorrow with Jamie, when
we are going to talk aboutmarketing, and this is one of
those hot button topics.
So I'm excited to see whatJamie has to say.
Welcome back to the Boss Responses podcast.
Today's episode is all aboutturning those one-off gigs into
long-term client relationships.
I know this is a big topic thatI've been hearing more about
lately.
I hope our discussion todayreally helps you.
If you're dealing with thisissue as well, let's get into it
.
If you're a freelancer,business owner or anyone who
(00:25):
deals with clients, you're inthe right place.
I'm your host, teresa Edmond.
I've been dealing with clientsand running my business for
nearly two decades and in thattime I've dealt with my share of
doubt, imposter syndrome andnot knowing what to say when a
client asked a question I wasn'tready for.
I created this podcast toempower you with the boss
(00:46):
responses you need to grow yourbusiness.
Each week, my guest co-host andI will bring you five episodes
packed with practical insights.
Monday through Thursday, weanswer your questions, and
Fridays, we dive deep to explorehow our co-hosts embrace their
role as the boss of theirbusiness.
Welcome to Boss Responses.
(01:08):
We are back for day two withJamie.
Jamie, what's the question fortoday?
Jamie Brindle (01:15):
All right, trace you ready for this one?
Yep, this is coming from Jen inDenver, colorado.
Jen says I've been freelancingfor about three years and I do
well with one-off projects, butI really want more long-term
clients.
I find that even when clientsare happy with my work, they
don't always come back.
What's the best way to turnshort-term gigs into ongoing
(01:38):
work?
Treasa Edmond (01:40):
I love this question.
You need to become a strategicpartner with your clients,
rather than a task completer.
If you are just completingtasks, they will have you
complete the task and then theymove on with their lives.
And we have to realize ourclients are busy people In the
corporate world.
They're stuck in meetings forlike seven of the eight hours a
(02:01):
day.
It's horrific for the poorin-house people and I'm sorry
for them, but we don't have todo that.
We focus on one client at a time.
To us it seems like we've donea really good job on this thing.
We've put in a lot of time.
We focused entirely on theirproject.
To them it's like I gave theman assignment.
They did it.
Now I can move on to the nextassignment and you might not be
(02:21):
the right person for that.
If you become a strategicpartner and you make yourself
valuable and you ask them theright questions that gets them
asking questions in-house, whichraises their stock in-house
you're going to be the firstperson they think of every time
they're going to say we havethis new project.
(02:42):
I'd really like to get Jen'sinsights on this before we
formulate everything, or we'dreally like to bring Jen in to
help us develop the brief onthis project so that we can make
sure we're hitting it right.
So you're providing a littlebit more strategy work and in
the process, you're getting paidmore, and then you're also
getting paid for the actualproject that you're completing.
(03:05):
I think that's about the onlyway to do it.
The other thing is to offerongoing retainers, and I still
do that by showing value.
This is what my clients getwhen they work with me.
As a retainer client, I becomemore familiar with your brand.
I require less oversight.
I turn in well-edited,ready-to-go turnkey content
(03:27):
every single time.
So you need to talk about theproblems you're solving for your
clients and the value you'rebringing, instead of just saying
I write blog posts.
So it's a messaging thing, it'sa marketing thing and it's
solving problems for yourclients.
If you want to go into thestrategy work, then that's one
way to do it.
If you want to do deeperconsulting work, that's
(03:50):
definitely, I think, thestrongest way to do it, but you
can also do it by formingrelationships with your clients,
letting them know from the getgo I work with all of my clients
long term, because this is whatyou get in return with all of
my clients long term becausethis is what you get in return.
And then they go into itthinking, ok, I don't need to
(04:10):
hire five writers, I only needtwo or three, because she's
going to take on the work of theothers and do it really well.
And then gradually you becometheir go to person for the more
important projects.
But how do you approach this,jimmy?
Jamie Brindle (04:24):
for the more important projects.
But how do you approach this,jimmy?
Yeah, no, I think all of thatis spot on.
Here's the thing the lifetimevalue of a client, optimizing
for repeat business this stuffis foundational to a successful
freelance business.
Yeah, so it is something thatyou need to figure out, because
what a waste if you go to allthe effort of acquiring a client
, of doing the marketing, doingthe advertising, doing the sales
(04:47):
, earning the trust.
You go to all that effort tojust do one project with them.
It's a waste of effort, if youask me.
Treasa Edmond (04:54):
I think so too.
Jamie Brindle (04:55):
It's optimizing for.
Okay, after that project.
How do I because, as youmentioned, they're busy, they're
not thinking about how do Ikeep Teresa employed?
How do I keep bringing her morestuff?
How do I keep bringing Jamiemore stuff?
It's incumbent on thefreelancer to say okay, after
that initial project.
How do I take them by the handand walk them to the next
project?
(05:15):
And then how do I take them bythe hand again and walk them to
the next thing?
This stuff needs to hire meagain, and they might.
But it might be eight and ahalf months from now when they
remember that they've got you inthe pocket.
(05:37):
You need to continue holdingonto that mantle of strategic
partner and bring them newsolutions to problems or say,
hey, usually, as you're handingthem the deliverable for the
first project, say usually oncesomebody's done this or once
somebody's got this in hand.
These are the next four thingsthat they're solving for, and
(06:03):
that's what I've seen in mybusiness.
And what do you think aboutthese four?
Are you coming up against anyof these?
It's like oh well, that one,well, great, I'm going to pull
this solution out of the folder.
Then here you go and we'removing on to the next one.
Treasa Edmond (06:10):
Yeah.
Jamie Brindle (06:11):
So it is.
It's really about designing theprocess of yes.
I mean, it's important to knowhow to make someone turn someone
from a stranger into a lead,into a client, and that's what a
lot of the content on theinternet is about and that's
what a lot of freelancers aresolving for.
But there's this fourth stepover here.
That's, I would argue, the mostimportant, which is how to take
(06:31):
them from a client to alifetime client.
If you can optimize for that,if you can build your business
on that concept, I think you'regoing to be in pretty good shape
.
Treasa Edmond (06:42):
And that's one of the main premises.
What's the right word there?
Jamie Brindle (06:46):
I think I was an English major and I should know
the answer.
But I'm going to go withpremises.
Treasa Edmond (06:51):
That's one of the main premises.
We're going to just stick withthat.
That's one of the main premisesof this podcast is, well, it's
two things that Jamie said.
One you're not just doing gigs,you're a freelancer running a
business.
Even if you think you're notrunning a business, you are, and
(07:12):
if you don't embrace that, thenit's never going to work.
It's just never going to workout the way you want it to.
If it does, it's accidental andthen it's not sustainable.
So you really do need to runyour business like a business,
which means planning, havingprocesses, all of that.
The other thing turning thoseclients into lifetime clients I
call that client management andit's something that I'm pretty
(07:32):
passionate about.
When we and this is a mindsetthing, it's also a wording thing
.
So Jamie used the word hiringand I said this on the podcast
before.
I never say my clients hire mebecause I'm not doing a job for
them.
When I'm talking to my clients,I use partnership language from
the very first communication.
That means if we choose to workon this project together, this
(07:55):
is what will happen.
So I talk partnership languageacross the way.
I never say hiring, I never sayjob, there are just certain
words I've mixed from myvocabulary when I'm dealing with
clients.
And it makes a huge differencein how they perceive me and that
and I take control of ourworking relationship not them,
(08:17):
but of our working relationshipfrom our very first
communication.
So I ask those pre-qualifyingquestions.
When they come on the discoverycall because they've met the
threshold for the pre-qualifyingquestions, I say thank you so
much for coming on this call.
I'm really excited to talkabout your project today.
This is what the call is goingto look like.
I'm going to ask you a seriesof questions so I can find out
(08:39):
more about what you want toaccomplish, who your audience is
, whatever the questions will be, and then I say and then at the
end I will take any questionsyou have and tell you a little
bit about my process.
Does that sound okay?
So they let you ask thequestions and then, by the time
they get to where they can askyou questions, you have already
asked insightful, strategicquestions about their project
(09:01):
and found out information theywouldn't have thought to include
.
So they see you as the expert.
They're ready to follow yourlead.
That means you get to be theexpert in the business
relationship and they get thefreedom to be the expert doing
what they do.
Jamie Brindle (09:14):
Absolutely.
Treasa Edmond (09:15):
It just makes it a more fulfilling relationship
across the board, full of mutualrespect.
That's how you turn them into alifetime client.
You lead them by the hand.
You make it so, so easy to workwith you not for you or you for
them.
You make it so much easier towork with you, to partner with
you, and I think it's a veryslight shift, but when you make
(09:38):
that, it changes everything inhow your clients treat you.
Jamie Brindle (09:42):
Absolutely.
Yeah, it is.
I think a lot of folks maybebecause they're coming from the
nine to five world or justbecause that's what's most
represented in culture what haveyou?
A lot of people think ofthemselves as a product on the
shelf as opposed to a strategicpartner.
A lot of people assume that theclient knows what they want and
(10:05):
that the client's got a plan,and that the client knows how
much it's going to cost to dothis.
And all of that is fallacious.
It's literally the client isrenting your expertise.
Treasa Edmond (10:15):
Yeah, that's the starting point.
That's all it is At the end ofthe day.
Jamie Brindle (10:18):
Yeah, you're coming in and there's going to
be a big sigh of relief if youestablish yourself as the expert
here.
It's not all right.
We're on this call.
What do you guys want from me?
What do you want me to do foryou?
That's not it.
They want you to tell thembecause you're the one that
spends your working hours inthis space.
If they knew what needed to bedone here, they wouldn't need
(10:40):
you.
So it's about assertingyourself as that expert and not
thinking of yourself as aproduct of the shelf, for sure.
Treasa Edmond (10:45):
Yeah, one of my favorite examples to use in a
situation like this, when we'retalking about giving the client
what they need instead of whatthey think they need, and then
establishing yourself as anexpert, becoming a street to
geek partner, all of thosethings.
It's very similar to thepricing issue from yesterday.
You can be low priced andthey're going to see you as a
low priced writer.
(11:07):
If you are a higher pricedwriter, they're going to say
that there's more perceivedvalue.
Well, in a situation like this,let's say my water heater won't
stay lit, because this happenedto me recently.
If my water heater won't staylit because this happened to me
recently If I call a plumber andsay my water heater won't stay
lit, I think I need a new pilotlight, and they just come out
and change the pilot light.
They're not a good plumber.
Exactly, they're not good atwhat they do.
(11:28):
If I say my water heater won'tstay lit, I think it might be
the pilot light.
They might say what's the modelnumber?
And I'll make sure I bring theright one with me in case that's
what it is.
But I'm going to have to dosome diagnostics to make sure
I'm solving the right problemand then they do all of the
things, I pay the very hefty fee.
My water heater now stays litbecause, by the way, it wasn't
(11:48):
the pilot light and then we itwas some random thing and he did
try changing the pilot lightand it didn't solve the problem
because he had to troubleshoot.
So, yeah, it's a matter ofshowing what the client needs,
because you have paid enoughattention to the situation and
you're not just giving them whatthey think they need, which is
(12:11):
only ever a partial solution.
Jamie Brindle (12:14):
Exactly, exactly.
Treasa Edmond (12:16):
Yeah, I love this question.
I love this question.
Thanks, jen.
All right, come back for daythree tomorrow with Jamie, when
we are going to talk aboutmarketing, and this is one of
those hot button topics.
So I'm excited to see whatJamie has to say.
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