Can You Really Trust Other Freelancers to Deliver?

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If you’re trying to go from freelancer to agency, hiring outside support often sparks anxiety. Can you really trust others to deliver for your clients?

In this episode, Tina shares her journey as a niche graphic designer and photographer. Though eager to grow beyond her one-woman studio, fears around freelancer reliability hold her back.

We explore practical strategies to test hiring help without jeopardizing client relationships built over 15 years.

Key Takeaways from this Episode:


  • Start with a one-off trial project to vet compatibility with freelancers before making long-term agreements.
  • Frame new hires to existing clients as added support for their benefit, not reduced attention.
  • Set clear policies around quality and timeliness so expectations are apparent.
  • Build initial buffers into timelines as you adjust to managing and collaborating.

Read on for actionable advice to move past doubt on leveraging outside talent.

Why Tina is Worried About Hiring

Tina introduces herself as a graphic designer and product photographer catering specifically to natural food brands. She launched her niche solo practice 8 years ago alongside homeschooling her young children.

While immensely enjoying the work-life balance of a simple microbusiness, Tina feels increasingly eager to expand. But one dilemma paralyzes her from venturing into hiring:

Can she really trust another freelancer to deliver client projects on time and up to her quality standards?

Tina acknowledges reliable talent abounds. But without firsthand experience collaborating beyond her own studio, uncertainty prevails. We explore practical baby steps to test the waters…

Start with a Low-Risk Trial Project

To minimize early risk, we advise Tina to structure an initial trial project with clear expectations and an easy exit plan.

For example, she might recruit a contractor for just one standalone assignment with a flexible deadline and limited scope of work. This allows both parties to vet fit with minimal lasting impact if things go awry.

Vetting compatibility upfront and starting slow is key according to Clay:

“You don’t know if they can deliver until you actually test them out. But you can run potential hires through a gauntlet to evaluate if it’s a fit.”

With a one-off contractor, Tina stays firmly in the driver’s seat while safely assessing collaboration readiness.

Frame the Client Perspective as a Win

When the time comes to share news of project support with her loyal clients, Tina worries about seeming disingenuous after 15 years as their sole point of contact.

We suggest keeping clients apprised of changes once new talent is firmly in place, not while testing trial arrangements. And frame the evolvement as added resources to augment her offerings, not reduced attention for them. This conveys ongoing commitment to top-notch partnerships.

As trusted advisors already embedded in clients’ businesses, Tina and her collaborators can present unified solutions tailored to ever-growing needs. Expansion should feel like a win for long-term partners if positioned thoughtfully.

Set Clear Policies to Safeguard Quality

To ensure control amidst introducing new collaborators, Preston and I advised instituting policies like:

  • Zero tolerance for missed deadlines
  • Right of refusal for subpar work
  • Mandatory lead time built into schedules
  • Sole point of contact remaining with Tina

By cementing expectations, the client experience remains protected regardless of behind-the-scenes shuffling. We encouraged transparent conversations so loyal partners feel involved in Tina’s growth, not excluded from it.

Find the Right Fit First…

In closing, we counseled Tina to dismiss worries about seeming disingenuous. Business evolution feels natural when properly communicated.

The priority is finding the right freelance fit first. Begin with low-risk projects focused on establishing alignment, not impressing clients. Once internal relationships solidify, external opportunities unfold far more smoothly.

For solopreneurs like Tina eager to engage support, collaborator compatibility unlocks growth. Vet slowly and reward trust on both sides. The solo days will quickly feel distant looking back!

Episode Transcript

This transcript was auto-generated and may have grammatical errors.

Preston (00:01.479)
Hello and welcome back to another episode of Freelance 2 Founder. My name is Preston Lee with Millo.co and joining me on the air today is my friend Clay Mosley from GetDripify.com. Hey Clay, how you doing man?

Clay Mosley (00:12.45)
Hello, hello. Doing good, man. I’m excited for 2024 podcasting season.

Preston (00:21.023)
That’s right, we are just getting started with 2024. By the time this airs, we’ll be a few weeks into it, but it just feels good to be back chatting with you. I missed you. And it’s just fun. How’s, do you have snow down in Texas these days?

Clay Mosley (00:30.954)
Hahaha!

Clay Mosley (00:35.926)
Uh, no, I’m, it’s like 70 degrees.

Preston (00:39.375)
Oh my gosh, I’m so jealous of you. We got like nine inches of snow yesterday, randomly out of nowhere. Like I pulled out of my garage to go to church and didn’t even really know it had snowed and all of a sudden I’m driving through like nine inches of snow. It was nuts. Well, we got plenty of it. Come on up. We got a guest room you can stay in and plenty of snow. So also joining us today, probably knows a little bit more about snow is my guest is Tina. Hi, Tina.

Clay Mosley (00:45.626)
I want the snow

Clay Mosley (00:55.682)
I want more of that. I want that.

Clay Mosley (01:02.996)
Hehehehe

Tina Zegel (01:09.393)
Hi, thanks for having me on the show.

Preston (01:12.035)
Absolutely calling in from Minnesota, right? Yeah, snow up there? What?

Tina Zegel (01:14.609)
Yes, Minnesota. Hardly. It’s very rare. Everybody’s scratching their heads, wondering where it is.

Preston (01:21.579)
Yeah, because usually you have a bunch, right? Yeah

Tina Zegel (01:23.609)
Yep, yeah, people are waiting to get on the ice to do all kinds of things and it’s not happening.

Preston (01:27.827)
Yeah, yeah, well, global warming and all that, whether you believe it in or not, I don’t know. But for some reason, we’ve had a fairly dry season too. Anyway, that’s pretty boring. So we’re going to move on. Tina, why don’t you tell us a little bit about and that was my fault. It’s boring. Not your fault, Tina. Tina, tell us about your business. Save me from this awful segment I’m doing here.

Tina Zegel (01:32.622)
Thank you.

Tina Zegel (01:40.789)
I’m going to go ahead and turn it off.

Tina Zegel (01:47.628)
Hahaha

Clay Mosley (01:48.599)
I was gonna let you keep going.

Preston (01:52.359)
Tina, why don’t you save me? Tell me, tell us a little bit about your business, what you’re working on, the services you provide, how long you’ve been in business. Just kind of paint a picture for us.

Tina Zegel (01:59.957)
Sure. So I have been working independently as a graphic designer and a food and product photographer for eight years. And prior to that, I actually did the math before this call because wow, I’ve actually been doing this for longer than I realized. I’ve been doing this for 17 years. And I started working for natural meat companies 17 years ago, and worked for them for quite a few years and then went out on my own.

Preston (02:10.264)
Oh cool.

Tina Zegel (02:29.893)
eight years ago. And since going on my own, I did that when I had two young children. So I have, by design, intentionally kept my business small. And it’s worked really, really well because I love what I do and I can make some decent income on my own schedule from my own home.

And yet I’ve been holding this tension for eight years, like when am I going to grow and how am I going to do it? And I spend so much time thinking about it and wondering about it. And then recently, I had this realization because I have so many dreams that are on hold on a shelf, like just building up for the one day when I finally decide that it’s time. And the reason it’s not time yet is because the way that I choose to educate my children, I homeschool them.

Preston (03:05.331)
Hmm.

Tina Zegel (03:28.281)
Um, and one day that may change or one day they may get older where I’m just less involved in a day to day. Yeah. So I’ve just been holding this question honestly for eight years because I love what I do. I love my job. It fills me up. I would actually do it and get paid nothing. So it’s a really nice bonus that I make a nice income doing what I love.

Preston (03:35.731)
Guaranteed they’ll get older. Yeah.

Tina Zegel (03:57.753)
Um, and then anyway, a couple months ago, I was listening to the podcast and I thought, here I am having this idea in my mind that someday I’m going to try to get a coaching call with Preston and Clay. And then it dawned on me, they might change their minds one day. They might, you know, have a career switch and decide their podcasts over. What am I waiting for? So I just, I really want to pick your brains because I don’t know if it’s going to be.

Clay Mosley (04:20.695)
Ha ha ha.

Tina Zegel (04:26.053)
in three months or six months or two years, but I really have a lot of confusion about how to grow because I definitely, I work in a silo. I am not, I am not an agency at all. It’s just me. I’ve been quietly doing my thing for eight years and loving it, but it doesn’t ever change. It’s just the same thing for eight years.

Preston (04:54.427)
I love how you’ve put it though. Like we talked to so many people who are like, oh, I’ve been, you know, working a day job for, and I was this, right? I’ve been working a day job for eight years, doing stuff on the side of thinking like one day, one day I’m gonna, you know, some magic something’s gonna happen or I’m gonna build up the nerve or whatever. One day, one day, one day. And I did that for so many years. And I love that you’re bringing up this point, which I’ll think a lot of freelancers face, which is like, things are good. Things are good enough, right? And

Tina Zegel (05:12.638)
and

Preston (05:23.731)
But there’s something maybe in the back of your mind, something deep down going like, oh, could there be more? Could there be more to running my own business? Would I have more fun or make more money or whatever and still be able to maybe have the lifestyle with my family that I want, homeschool my kids, whatever that your priorities are. So I love that you brought that up because I think that happens to all of us in one way or another.

Tina Zegel (05:48.581)
Yeah, I just, the limbo is odd. I never thought, well, in so many ways, life is not what we think it is when we get to the next season. But I’ve been holding this question for so long and I’m like, I don’t wanna wait another eight years. I don’t even know if I wanna wait another year. I wanna find out and I really wanna test the waters with what is it even like to hire somebody? I might decide I hate it, but I don’t like not knowing. I really wanna try it.

Preston (06:07.283)
Yeah.

Tina Zegel (06:18.201)
And I hear you guys talk a lot about hiring people. Should I hire people? Because some people choose not to. Some people choose to just stay independent. But I guess in my mind, I can’t even picture how to do that logistically and how to do that in a way that’s not really high risk. Because I guess I feel like one of the, I’m not a designer that thinks.

Um, I don’t hold a belief that there’s not another designer that can do good work. I am well aware there are plenty of designers that do work a lot, like even stronger than my work. I just have this fear of them not delivering and also delivering. Maybe on time. So then what do I do to communicate to my client? Because I have a really good track record of knowing what I can get done.

when and when I can get it done. And so I think that’s my big fear. I know that there’s capable designers and I think my fear is that they won’t deliver on time and then what do I do? I kind of back myself into a corner.

Preston (07:34.703)
Yeah, okay, that’s a tough one. And I love that you bring that up. I think this is something we don’t talk a lot about when we talk about hiring and that is, and Clay and I have faced this ourselves, right? And that’s that you hire someone and they don’t deliver or they deliver late or their quality is way lower than what you thought it was gonna be. And that is a real challenge. And just to bring everyone up to speed quickly too, you put in your survey as you prepared for the show.

Clay Mosley (07:44.423)
Mm-hmm.

Preston (08:03.123)
And if you wanna come on the show, if you’re worried that Clay and I are gonna stop podcasting next month, also, which we’re not, but we would love to have you as soon as possible. I love that Tina, you just were like, you know what, I’m just gonna do it. And we’d love to have you listener on the show as well. You just visit free and you scroll to the bottom of the page, you fill out a quick questionnaire. On that questionnaire, one of the questions is, on a scale of one to 10, one being a freelancer, 10 being a founder, where would you put yourself?

Clay Mosley (08:07.416)
Hahaha

Preston (08:30.667)
and where do you want to be, right? And you put that you’re currently at a two, you’d like to be at a four. And to me, yeah, one of the big differentiators between a two and a four is you’ve hired someone, even if it’s just a contractor, right? It doesn’t have to be a full-time employee. And so I love that you’ve brought up this concern, which is like, how do I know I can rely on somebody? And we’ve talked about, like you said on the show, to think that you’re the only designer that can do well at design is sort of…

ridiculous in a way, right? And so I’m glad that’s not the issue. The issue is how do I know someone’s gonna deliver and if they don’t, what do I do to maintain a good client relationship? So I have some ideas, but Clay, is anything bouncing around in your mind as you hear some of the concerns that Tina’s bringing up?

Clay Mosley (09:11.177)
Mm-hmm.

Clay Mosley (09:16.43)
Yeah, so I can tell you right now hiring your first person is the most is the most nerve wracking thing. The first hire is always the yeah it’s the toughest one. It gets way easier after that, but the very first one is tough because I remember, I remember the first time I hired somebody and

Preston (09:30.631)
Yeah, that first one’s tough.

Clay Mosley (09:45.274)
I was in a, financially I was in a position where that first person was getting paid more than me. You know? And that’s just, that’s just the reality of startup. You know, it’s like you put your money back into, I’m not saying this is going to be true for you, Tina. But my point is, is I was super, super nervous about it. I’m going to kind of burst your bubble here a little bit.

Preston (09:54.159)
Yep

Clay Mosley (10:10.05)
You don’t the question is how do you know they’re going to be able to deliver you really don’t know until you actually hire them Now I will say this Yeah, I will say this though because I have i’ve had i’ve hired a many people um both as w2 employees, um, and as contractors like probably at least Total hires probably at least four dozen

Tina Zegel (10:18.037)
Nothing to be proud of, hoping for.

Clay Mosley (10:38.71)
in the last eight years, there are things that you can put in place to minimize the impact it will have on your business to at least try them out. So to answer your question, you’re not going to know until you put them to the test, but you can run them through, I don’t know, basically a gauntlet, basically what I call it to see if they’re going to fit.

Preston (11:06.427)
Yeah, I agree with that. I am a firm believer that it’s not okay to get free work during the application process, but I think there is opportunity where you could pay someone on a one-off project, right? So like, let’s say you have a project, Tina, that has plenty of runway. Maybe the next time a client comes to you and says, I want this and this done, you bid it out, but you give them a timeline that’s maybe twice as long as you would normally take.

Clay Mosley (11:13.506)
soon.

Preston (11:33.999)
And then you find a contractor that you hire just for that project, right? It’s not a long-term arrangement, it’s not permanent, there’s very low risk, and you hire them for this one project, and maybe you find them through a marketplace or through your network or something like that, right? And you just hire them one-off. And you may even give them the bulk of the payment of that one project just to expedite the whole process, right? And then you give them a deadline.

Tina Zegel (11:59.285)
Thank you.

Preston (12:02.619)
And then you see how they respond. And because you’ve given yourself a really long timeline on this singular project, then worst case scenario, if they don’t deliver on time, you can either take a late project from them and still deliver to your client on time, or you could step in and just do the project. Yes, it might be a pain, but that would be again, worst case scenario, right? Ideally, middle case scenario, they’re like a few days late or something, and then perfect case scenario, they deliver on time. And so,

Tina Zegel (12:20.169)
Mm-hmm.

Tina Zegel (12:23.633)
Mm-hmm.

Preston (12:31.023)
I think you can start really small. Sometimes we think we use the word hiring and it’s like, well, I gotta find someone who’s gonna be permanently on my team. Almost everyone that I’ve hired on my team, I started with like a one-off project first. Well, that’s not true now, but I would say early on I did. And it was like, can you write an article for the website or can you design this thing or can you develop this plan or can you come up with ideas for XYZ? And I just paid them for one project.

And then I got an idea of how they actually work, how they communicate, when they deliver, all of those questions you have that are a black box right now, they all become very, very clear in working with that person on a one-off project. And then if that goes well, and you can even say to them upfront, if this goes well, I have, you know, I would love to figure out a long-term thing, but I wanna make sure it works out well for both of us before we commit to something, you know, more in depth. Yeah.

Clay Mosley (13:24.042)
Yeah, be transparent about that.

Tina Zegel (13:27.593)
That makes sense, thank you. So it sounds like I’m just really need to build in buffers for the just in case they don’t deliver.

Preston (13:38.011)
Yeah, I think that can be helpful in the beginning. And then you’ll start to get a feel for like, and it will, cause it will also take longer naturally because there’s extra communication happening, right? So you do want to build in a safety net so that you’re not over promising to your clients and then under delivering by missing deadlines.

Clay Mosley (13:38.207)
Yeah.

Tina Zegel (13:48.402)
Mm-hmm.

Tina Zegel (13:56.295)
Mm-hmm.

Clay Mosley (13:56.462)
But you want to do that anyway, even if you were doing it on your own, you know?

Tina Zegel (14:00.901)
Right, yeah, I think I do that to a point, but I do…

Tina Zegel (14:09.873)
I don’t know, somehow it just seems to work out. I do have some pretty tight deadlines and big promises to my clients with a little bit of buffer, but I would probably have to double or triple it if I were delegating, even when you think about the time that it takes to delegate and communicate.

Clay Mosley (14:31.531)
your typical project.

Tina Zegel (14:33.533)
So I forgot to mention, I only work for natural food brands. So I live in a very niche market, which I love. So my projects could be anywhere from a new logo or brand identity, which to be honest, that doesn’t happen very often because I only have a few clients. So I more regularly build things like food labels, packages, brochures.

Um, I-

Clay Mosley (15:04.198)
Okay, let’s take a food label. How long does its food label project take?

Tina Zegel (15:11.721)
Um, it could take anywhere from 10 minutes to many hours, honestly. I did.

Clay Mosley (15:13.055)
on average.

Preston (15:19.315)
But from the time, from the time, yeah. Like from the time that the client agrees to do the project until you deliver it, is that a week, a couple of days?

Clay Mosley (15:19.37)
Well, from a calendar timeline.

Tina Zegel (15:28.377)
Okay, so I know you guys probably want an easy answer on this, but I really only have a few clients. And I almost just kind of merge myself into as a member of their team. And when I first start working with them, when I first start working with a client, I send them project estimates. And then I move away from that after they trust me. And I just charge them everything they send me.

Preston (15:32.935)
Hahaha

Preston (15:40.765)
Mm-hmm.

Tina Zegel (15:56.921)
I tell them when I think I’ll be able to get it done, and then I charge by the hour.

Clay Mosley (16:03.463)
Okay, so…

Tina Zegel (16:04.057)
So literally they might, they could send me a project that takes me 10 minutes, or they could send me a project that takes 40 hours.

Clay Mosley (16:12.706)
Let me build a hypothetical situation. I’m a client that I already trust you. And I said, I need a label for this food product. Here’s my money, boom, I paid you. How long will it take? I’m asking as a client in this hypothetical situation. How long will it be? What’s the delivery time?

Tina Zegel (16:15.321)
Okay.

Tina Zegel (16:34.921)
Yeah. So let’s see.

Tina Zegel (16:41.269)
So I would tell them it’s gonna take me two weeks.

Clay Mosley (16:44.93)
Two weeks, okay. So if you were to hire somebody to help you with this, I don’t know, and this is just like, I’m just going off and maybe Preston can chime in here, but I’m just basing this off of my experience with hiring someone and working with them. I don’t think it’s gonna double or triple your time. I really don’t.

Preston (17:12.796)
I agree with that. Yeah.

Clay Mosley (17:13.934)
I think it’s going to maybe, I would add in 20, 25% more, in my opinion.

So instead of two weeks, maybe you could maybe make it like two and a half weeks.

Tina Zegel (17:23.631)
Okay.

Preston (17:34.715)
I agree, and I think if you’re really, really worried about a freelancer delivering, I referenced what we talk about sometimes on the show and I think you referenced it as well, Tina, and that is like to think that you’re the only person that can do that work is just, it doesn’t make any sense, right? There’s so many talented people. And so you recognize that. I think it’s also important to recognize there are so many people who can deliver.

Clay Mosley (17:52.12)
Mm-hmm.

Preston (18:01.759)
good quality projects on time and they do and they make a living doing that just like you do, right?

Tina Zegel (18:07.162)
I think it maybe doesn’t seem real to me because I’ve never done it.

Preston (18:11.668)
Mm. Yeah.

Clay Mosley (18:11.818)
Let me tell you, let me tell you, let me tell you what’s gonna happen. Um, you will, you will find some people that mo as you hire people. I just want to set expectations. They will do. Most of them will do about 80% as good as you will.

Preston (18:31.548)
Yeah, that’s right.

Clay Mosley (18:32.866)
A good one. So I want to set that expectation with you because if you’re expecting 100% as good as you, that’s rare. That is rare. They don’t care. Yeah. They will do about 70, 80% as good as you. You will though, as you get into this and you keep growing, you need more people, what will happen is you will find somebody who’s better than you.

Preston (18:40.767)
They don’t care as much as you. It’s not their business, right?

Tina Zegel (18:43.837)
Yeah.

Tina Zegel (18:48.302)
Mm-hmm.

Tina Zegel (19:01.073)
Mm-hmm.

Clay Mosley (19:02.134)
which is awesome, right?

Tina Zegel (19:04.121)
and doesn’t want to be running a business. They just want to be doing design, and then they’re willing to work for somebody else.

Clay Mosley (19:07.378)
Yeah.

Preston (19:08.239)
Yep.

Clay Mosley (19:11.63)
Uh-huh. But I’m just going to tell you, I just wanted to give you that expectation that most of them, they’re going to do 70 to 80 percent as good as you.

Tina Zegel (19:20.611)
Mm-hmm.

Preston (19:22.507)
The other thing I would add too is like during the interview process, as you’re vetting people, it is perfectly acceptable for you to say, I have a zero tolerance policy on late projects is how do you feel about that? Right? Like, like if, if you turn something in late, we’re not going to be able to work together on another project. That’ll be the end of it. So I mean, that’s a very hard line in the sand, right? But if it’s that important to you, it’s okay to bring that up. And

Tina Zegel (19:35.201)
Okay.

Tina Zegel (19:45.99)
Thank you.

Tina Zegel (19:49.617)
Mm-hmm.

Preston (19:50.511)
And you might in real life be more lenient, right? But getting their reaction to something like that is important. If they say, oh, no problem, I feel the same way. I hate it when things are late and I’m always on time and my clients love that I deliver early and da da, right? Then yes, it could be lip service, right? They could be making it up, but I think you can at least get a sense of how they respond to something.

Tina Zegel (19:53.362)
Thank you.

Tina Zegel (20:06.555)
Yep.

Tina Zegel (20:16.526)
Yeah, thank you for that. That makes sense. It’s interesting. I’m thinking about this building in a buffer to minimize the risk of hiring somebody. But it feels like ideally if you find the right person, if anything, it should go faster, right? Because there’s one of me.

Clay Mosley (20:32.81)
It should go faster. Yeah.

Yeah, it should go faster. But at the beginning, when you’re trying to find the right person, I think it’s good to build about 20% more.

Tina Zegel (20:48.038)
Mm-hmm.

Clay Mosley (20:48.842)
Because, I mean, you could go through one, two, three, five people before you find someone that’s like a right fit.

Tina Zegel (20:53.493)
Mm-hmm.

Okay.

Preston (20:56.911)
Yeah, I think for me that buffer idea was more like on this example of find a one off project, find a one off freelancer, give it a test ride. Cause you’re also going to learn things about yourself, Tina, about how you manage, how you communicate, things you didn’t know about that process, things you weren’t expecting about that process, right? You find someone in a different time zone and all of a sudden you realize like communication is not as instantaneous, right? I have someone on my team who works in Pakistan and he does a great job.

But there are sometimes when I’m like, I need this thing urgently and it’s like, oh, it’s 2 a.m. right now. I’m not gonna wake him up to solve this problem, right? So, you know, there’s gonna be things that come up and so I think particularly on that first run, you wanna build in, I’d build in a little bit more than 20 or 25% on that first one just to learn how things work. And then as you get better at it, you can kind of bring that buffer down. And then at some point, like you said, you may not need a buffer anymore, right? It might actually happen more quickly.

Tina Zegel (21:50.869)
Mm-hmm. So I have another question. Is this a good time for it? OK. I also hear you talk on the show about not apologizing to your clients that you have a team and that you’re no longer just an independent. And I understand that. And I would definitely, over time, want to communicate to my clients that I am, in fact, working with other people. And I do already have it written into my contracts with my clients. They’ve signed on the dotted line.

Preston (21:56.033)
Yes, let’s do it.

Tina Zegel (22:20.881)
about that I might hire somebody, but they all know that I really haven’t. And so I’m curious if you have an opinion on when I hire somebody, say it’s a subcontractor, and I’m just testing the waters with them. Do you feel like it would be a good idea to actually wait to tell my clients, like, wait until I’m not just testing the waters and I feel like this is really working?

And now I really am going to do this and then communicate to them that.

Clay Mosley (22:54.526)
I would wait. I would wait. Well, okay. So whenever I say I would wait, I whenever you’re you are trying somebody out, I consider it as a trial period. They’re not actually someone who you’re going at least at that point not they’re not someone who you are going to use on a regular basis. Now you can From your client’s perspective, you are working on it right

Tina Zegel (23:04.83)
Yeah.

Tina Zegel (23:15.551)
Mm-hmm.

Clay Mosley (23:23.446)
But from your perspective internally behind the scenes, you’re working with this other person. And I personally don’t think that’s unethical because you’re still managing the project. But if you get to the point where like, you’ve gone through this trial period with this person, okay, you’ve gone through two, three, four other projects with this person, okay, now it’s pretty solid that, okay, I’m gonna keep working with this person.

Tina Zegel (23:35.06)
Yes.

Clay Mosley (23:52.446)
At that point, you could do an introduction to your clients and say, hey, let’s welcome so-and-so to the team. That’s what I would do.

Tina Zegel (24:04.085)
Mm-hmm. Okay. I think it feels odd to me because some of my clients I have been working with for like 15 years. And so I get the whole thing about, it could be a really great thing, it could even work out better for them if I have somebody else on my side. It just feels odd to me to be working behind the scenes to not just be one person and then.

I don’t know, because it’s not just a, they’re not just a business client, you know, I’ve known them for 15 years. And I’m also in a position where I like to be, which is I have a few clients and that’s where I want to be. And I, it’s really lovely because I love all my clients and I’ve had other people reach out to me and ask for work. And I just get to say no and not feel bad about it. So I really, really love that I get to choose my clients.

Clay Mosley (24:38.691)
Mm-hmm.

Tina Zegel (25:02.577)
because…

Clay Mosley (25:05.11)
Well, let’s talk about why does it feel odd to you?

Tina Zegel (25:10.426)
Um, I guess it feels a little disingenuous, like, because I am a pretty open book just in general about my, about myself and the way I do business and I don’t know, it just feels odd. I don’t know if I can put words to it.

Clay Mosley (25:13.678)
Mm-hmm.

Clay Mosley (25:27.79)
Mm-hmm.

Preston (25:28.013)
like you’re being deceptive?

Tina Zegel (25:29.874)
Maybe, yeah.

Clay Mosley (25:32.491)
At the end of the day though, is it your name that you put your stamp of approval on it?

Tina Zegel (25:39.633)
Yes, like I would, yeah, especially in the beginning as I’m building trust with somebody, they really, this other person really would be behind the scenes. And I wouldn’t, at least in the beginning for sure, I would, you know, all the communication and all the deliverables would be through, from me to the client. So I guess it shouldn’t matter. It’s just.

Clay Mosley (25:49.111)
Mm-hmm.

Clay Mosley (26:02.582)
Wait, so when you say it feels odd, are you talking about like whenever, like at the beginning while they’re on a trial period, or are you talking about once they become like, quote unquote, part of your team, and now they’re working with this client that you’ve had for 15 years instead of you?

Tina Zegel (26:20.861)
I think both, but more so the first one. Me. Yeah.

Clay Mosley (26:26.337)
Okay.

Clay Mosley (26:30.399)
I think it’s just new. I think that’s quite honestly, I think that’s what it is. This is a very, very normal thing, by the way. It’s a very normal thing. And I think in the first situation when someone’s in a trial period and you’re working behind the scenes with this contractor, at the end of the day, you are putting the stamp of approval on it. You are still delivering it to your client. It’s not this other person, it’s you.

Tina Zegel (26:37.191)
Okay.

Preston (26:40.08)
Absolutely.

Tina Zegel (26:58.473)
Mm-hmm.

Clay Mosley (26:58.858)
So I think that that’s okay. In the other situation where let’s just say, okay, this person’s working out, I’m now going to let this contractor manage, not manage, but do client communication directly with this client that you’ve had for 15 years. I can see where that could be. Yes, that’s a…

Preston (27:24.499)
to me is a way bigger step.

Tina Zegel (27:26.548)
Yeah.

Clay Mosley (27:27.518)
much bigger step and I think if you have a client who’s been working with you for 15 years, they’re friends with you at this point, right? I think if they’re true friends, they’re gonna be happy for you that you’re growing.

Tina Zegel (27:37.261)
Yeah, yeah, because

Tina Zegel (27:47.075)
Mm-hmm.

Preston (27:50.163)
And really at the end of the day, they need, they need the deliverable, the value that you’ve been delivering all this time, right? And yes, I’m sure they value your friendship and everything else that comes with working with you. But at the end of the day, like they, the only reason this would go wrong is if you have someone else working with them and they’re not delivering the same quality of project that you deliver, right? And-

Tina Zegel (28:17.351)
Right.

Preston (28:18.139)
And so then it becomes like your job becomes quality control, both in the communication and in the project itself. And you have to oversee that. And, and I would, I would make that clear with your client, particularly if you’re deciding, if you’re trying to decide, like these people who I’ve worked exclusively with for 15 years and it’s just been me, I think I would say if, if I were in your shoes, I would say to them privately,

Tina Zegel (28:25.376)
Mm-hmm.

Preston (28:43.323)
Whenever you feel like it’s right to introduce them to this news person, right? I would also say to them privately and in addition to an introduction where the other person’s involved, I would then say, and also, I want you to know how important our relationship is. I have loved working with you. I’m going to be very, very involved in your projects, but you may communicate a little more with this person. If you ever have any issue or concern or question or anything or feel like you’re not getting a response or if you just anything, please come to me. I’m 100% available.

you can still reach me as you always have. But I’m just trying to, you know, get your projects done a little more quickly or bring a little more extra creative flair or something like that, right? Like you really end on a positive, but let them know that you’re there 100% for them still.

Clay Mosley (29:18.625)
Mm-hmm.

Tina Zegel (29:19.984)
and

Tina Zegel (29:25.173)
Mm-hmm. Okay. So do you ever hear of people growing a business in a way, like hypothetically speaking, in a year from now, say I’m no longer homeschooling my children and I suddenly had a lot more time and then I went and found more work? And what would you think about me kind of continuing my business as is with the clients that I loved and

used to be employed by some of them, and now they’re a client of mine. And then if I took on new clients and kind of treated them differently, like they are the clients that are working with a team more than just myself.

Preston (30:04.498)
Yeah.

Preston (30:12.351)
I think there’s nothing wrong with that as long as you just understand where your time’s going to be spent, right? Like how much time am I going to have to continue to dedicate to my clients that I want to just work one on one with? I think there’s nothing wrong with that. In fact, that’s your prerogative as a business owner to say like, these are the clients and projects I want and then everyone else can have these other ones that are going to help pay the bills but that I’m not super passionate about or I don’t have a long history with or whatever. There’s nothing wrong with that. And I think actually that could be a good segue or a good…

Clay Mosley (30:16.779)
Yeah.

Tina Zegel (30:37.045)
Mm-hmm.

Clay Mosley (30:38.67)
Mm-hmm.

Preston (30:41.511)
sort of bridge between where you are now and where you wanna be, because at some point then, your current clients, who you’re worried about, that we’ve been talking about, maybe they get wind from another client that you have this team, right? And they’re like, whoa, hold on, you have more resources we could tap into or whatever? And you’re like, yeah, I’ve got a writer and a whatever, and we’d love to help you with these projects. Or you bring it up yourself and you’re like, hey, just so you know, over the last year, I’ve added…

Tina Zegel (30:56.821)
Thank you.

Tina Zegel (31:04.361)
Mm-hmm.

Preston (31:10.827)
us, this person and this person to the team, which means we can now offer these services if there’s something we can help you with. We’d love to do that. You know, and it just, yeah, I think it provides opportunity to bridge that gap a little bit.

Tina Zegel (31:17.651)
Mm-hmm.

Tina Zegel (31:22.689)
Mm hmm. Yeah, I’m not sure why I didn’t think of that before, but I’m glad we’re getting on this call because that really does make a lot of sense to me.

Preston (31:33.383)
Oh, good. Good. Great. Yeah. I think, you know, hiring, it is a hard one, but a lot of it is in our head, right? If you think about most businesses, most businesses have people working in the business and as the business changes and grows, it needs more people and different people and people are used to that, right? That’s just how it works. But we get so caught up in our own head of like, oh, are they going to be mad? Are they going to feel ignored? Are they going to? Well, put…

Tina Zegel (31:40.597)
Mm-hmm.

Tina Zegel (31:47.931)
Yeah.

Clay Mosley (31:48.322)
Mm-hmm.

Tina Zegel (31:54.42)
Mm-hmm.

Preston (32:02.207)
Put things into place so that they don’t feel ignored. Give them plenty of notice so they don’t get mad and surprised by it and confused by it, right? All of these things like paint out worst case scenarios and say, how am I gonna handle this ahead of time so this worst case scenario doesn’t happen, right?

Clay Mosley (32:05.367)
Mm-hmm.

Tina Zegel (32:09.127)
Mm-hmm.

Tina Zegel (32:17.702)
Mm-hmm.

Clay Mosley (32:18.478)
Yeah. Hey, one thing we haven’t mentioned yet is, one thing to kind of like test the waters with someone is maybe you just give them a small part of a project.

instead of a whole project. You know, maybe it’s something that’s, you know, maybe it’s just something that’s like, I don’t even know. I’m not as familiar with, maybe Preston. Preston’s graphic design, but, you know, maybe there’s like more like the setup or whatever with graphic design that somebody can do and then you take over. You know what I mean? The main part.

Tina Zegel (32:35.015)
Yeah.

Preston (33:00.411)
Oh, I love that idea. Or you could even say like, I feel like I’ve gotten this, you know, you mentioned package design earlier. I feel like I’ve gotten this package design maybe like 75% of the way there. Can you take a look at it and just, what would you change or tweak? Maybe you can get it the rest of the way there and just see how they’re able to compliment your ideas, right? I think if you don’t wanna be stepping away entirely from that creative process, which I’m gathering you don’t want to, I think it’s important to see how you can work together.

Right? And it might be that the people you hire just help you. Maybe you still work on all the projects, but maybe they cut down your time that you spend individually on them by 50% or something. By them, maybe you do general concept, you get it close, and then you send them a PSD file and they finish it out or whatever. Right? And that just allows you to do more projects in the same amount of time. I think there’s lots of options there. I like that. I like that way of thinking about it, Clay.

Tina Zegel (33:30.453)
Mm-hmm.

Tina Zegel (33:49.029)
Mm-hmm.

Tina Zegel (33:57.606)
Mm-hmm.

Yeah, thank you. I kind of feel like I’m so deep in thought over what you’re saying. I’m not sure what I have here.

Preston (34:05.467)
Hahaha

Clay Mosley (34:08.194)
You know, on that, just one more note on that, you could hire someone who is not even a graphic designer because I’m sure you have a lot of administrative type work that you have to do.

Tina Zegel (34:22.477)
Yeah, you know, it’s funny, I think it was Preston, you that said that you assumed that I would want to be kind of in the, in the lead and very involved, especially with new projects and things and a part of me kind of wants to even test the waters with stepping away from that because or even maybe collaborating with somebody because I get the thing about I could just spend time and

Preston (34:30.943)
Mm-hmm.

Tina Zegel (34:50.285)
money, mostly money to outsource some administrative things. Which when I do grow my business, that seems like a no-brainer that I will do. But I actually kind of sometimes, I just want to collaborate with designers too. Like I’ve been working in a silo for so long. I think I’m more fearful that somebody’s not going to deliver

Clay Mosley (34:53.591)
Mm-hmm.

Tina Zegel (35:18.557)
the right quality on time, then I am actually releasing some pretty sizable projects to somebody to just see what that feels like. To see it. Yeah.

Preston (35:23.475)
Hmm.

Preston (35:30.099)
Well, I love that you’re thinking about it that way. And I would just remind you again, then that there are plenty of designers who deliver on time, deliver early. Um, yeah, I think it may take a minute to find the one who works on your, on your best timetable, but you know, there’s, there’s lots of reliable freelancers out there, talented, reliable freelancers.

Tina Zegel (35:45.981)
Mm-hmm.

Clay Mosley (35:51.394)
Mm-hmm.

Tina Zegel (35:52.47)
I know it should be the most obvious thing and for whatever reason I’m like stuck on the side of this giant wall there’s all these capable designers on the other side of it

Preston (36:05.719)
And the only way to overcome that is to have and have a positive experience, right? They say experiences create beliefs. You have somewhere along the line, you’ve had an experience or more than one maybe where someone hasn’t delivered, right? And so you’ve built up this belief in your mind. And so you need to have some positive experiences. You need to find some freelancers who give you a positive experience in terms of deadline. And that’ll start to change. And you’ll start to go, huh, okay, people can deliver on time. I can trust them to do that.

Clay Mosley (36:10.07)
Mm-hmm.

Tina Zegel (36:35.866)
Yeah, I hope in six months or 12 months whenever I decide to give it a go, I hope I can just get back on the on a call and say I did it and it worked well and best thing ever.

Clay Mosley (36:47.342)
Mm-hmm.

Preston (36:48.103)
Well, we hope so too. It’s been a real pleasure chatting with you today. This has been fun for me. We’ve talked about some things we’ve never talked about on the show before. So thank you, Tina, for having the courage to come on the show and let everyone hear what you’re up to. If you would like to join us, we’d love to have you listener. Please visit free and then just scroll to the bottom of the page, sign up for a time and we chat about your business. Tina, before you go, will you let everybody know where they can connect with you in case they want to work with you?

Tina Zegel (37:16.277)
Absolutely. So I am on LinkedIn. I’m embarrassed to say I don’t know my exact URL to get there, but my website is TinaZigel.com. It’s T-I- And from there, you can find me on LinkedIn also.

Preston (37:35.839)
I love it. Tina, thank you so much. I’ve been Preston from millow.co, and of course, Clay from getdripify.com. Thanks for joining us today, Clay. We’ll talk to you guys next time.

Clay Mosley (37:36.654)
Perfect.

Clay Mosley (37:45.087)
See ya!

Tina Zegel (37:45.929)
Thank you.

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Written by Preston Lee

Editor at Millo.co

Preston Lee is the founder of Millo where he and his team have been helping freelancers thrive for over a decade. His advice has been featured by Entrepreneur, Inc, Forbes, Adobe, and many more.

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