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How High-Performing Creatives Get Stuck with Stacey Bailey (stage 3) - Ep. 396
Episode 39619th May 2026 • The Start, Scale & Succeed Podcast • Scott Ritzheimer
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In this insightful episode, Stacey Bailey, Senior Consultant & Executive Coach of The Intention Collective, shares how creative founders can successfully lead their first team in stage 3. If you feel frustrated that no one else can keep up, think like you, or deliver the way you do, you won't want to miss it.

You will discover:

- Why expecting your team to think and work like you creates unnecessary struggle and misalignment

- How to create clarity around vision and expectations so everyone rows in the same direction

- What it takes to build real trust and give effective feedback instead of being “nice.”

This episode is ideal for for Founders, Owners, and CEOs in stage 3 of The Founder's Evolution. Not sure which stage you're in? Find out for free in less than 10 minutes at https://www.scalearchitects.com/founders/quiz

Stacey Bailey is a leadership coach, strategist, and facilitator who helps entrepreneurs and creative leaders build businesses with heart. A certified System and Soul™ Implementor and Dare to Lead™ Certified professional, she brings more than 15 years of experience in leadership and operations within the creative services industry. Today, through Intention Collective, Stacey partners with founders and leadership teams of creative agencies generating $1M–$15M in revenue to build scalable, values-driven businesses. Her expertise includes leadership development, operational alignment, and strategic planning, and she has successfully supported organizations through private equity transitions, B Corp certification, and international expansion.

Want to learn more about Stacey Bailey's work at The Intention Collective? Check out his website at https://intentioncollective.co/

Email her at stacey@intentioncollective.co

Check out Stacey's personal website at https://www.stacey-bailey.com/

Connect with Stacey through her LinkedIn at https://www.linkedin.com/in/staceylbailey/

Mentioned in this episode:

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Transcripts

Scott Ritzheimer:

Hello, hello and welcome. Welcome once again

Scott Ritzheimer:

to the start, scale and succeed. Podcast, the only podcast that

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grows with you through all seven stages of your journey as a

Scott Ritzheimer:

founder, I'm your host, Scott Ritzheimer, and today's episode

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centers on all those high achieving founders out there,

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creatives, dreamers, visionaries and the like, who are really

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good at what they do. You know who I'm talking about? You know,

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if this is you like you just crush it. And as the team around

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you starts to grow, as you start bringing more people into the

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fold, the problem starts to pop up that it just seems like no

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one else can keep up. They don't think like you, they don't act

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like you, they don't make decisions like you. They don't

Scott Ritzheimer:

work the hours that you do. And all of this starts to grow, and

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as the organization gets bigger, so does the frustration of

Scott Ritzheimer:

trying to keep everyone moving in the same direction. Now

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here's the bad news, that the very thing that made you

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successful is also the very thing that's likely to sabotage

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you at this level, as a leader, you can't out craft your way

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through a people problem, and most creative founders learn

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that the hard way. But the good news is that Stacey Bailey is

Scott Ritzheimer:

here with us today. Stacy is a leadership coach, strategist and

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facilitator who helps entrepreneurs and creative

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leaders to build businesses with heart. She's a system and soul

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implementer and a dare to lead certified professional who

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brings more than 15 years of experience in leadership and

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operations within the creative services industry today, through

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the intention collective Stacy partners with founders and

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leadership teams of creative agencies generating one to 15

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million in revenue to build scalable values driven

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businesses. Her expertise includes leadership development,

Scott Ritzheimer:

operational alignment and strategic planning, and she has

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successfully supported organizations through private

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equity transitions, B Corp certification and international

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expansion. Stacy, welcome to the show. Glad to have you here.

Scott Ritzheimer:

Would love to just dive in right out of the gate creative agent.

Scott Ritzheimer:

You work a lot in the creative agency space, and I have found

Scott Ritzheimer:

that this level is particularly hard for folks like that.

Scott Ritzheimer:

They've they've hired their first handful of people, and

Scott Ritzheimer:

there it's something not right. What's going on here?

Stacey Bailey:

Well, thanks for having me, Scott. You know,

Stacey Bailey:

usually these folks got into their roles because they were

Stacey Bailey:

great at their craft. And then, you know, we get more people in,

Stacey Bailey:

and they are like, Why can't these people do this the way

Stacey Bailey:

that I do this? And usually they've elevated themselves into

Stacey Bailey:

a little bit of a pickle, right? So what we tend to find is that

Stacey Bailey:

we've got founders who are makers, and they go, I can't

Stacey Bailey:

take it all. I've been doing all of it for too long, and I'm

Stacey Bailey:

exhausted. But now I don't quite know how to convey clearly what

Stacey Bailey:

good looks like, what excellent looks like, how I want these

Stacey Bailey:

people to elevate in their craft, so that I can let go of

Stacey Bailey:

the reins a little bit.

Scott Ritzheimer:

Yeah, I think one of the things that makes

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this hard is that for high performers who have the style,

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makeup, guts to go out and start their own thing with all the

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risk that comes with that, they tend to also be the type of

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folks who don't really like to be managed a whole lot and and

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so one of the things that I think they do is impose that

Scott Ritzheimer:

view on others as well. Do you see that happening in the

Scott Ritzheimer:

creative space?

Stacey Bailey:

Absolutely, these people started businesses

Stacey Bailey:

because they didn't want to work for someone else, right? And

Stacey Bailey:

they then they are saying, well, you need to go and be as

Stacey Bailey:

entrepreneurial as I am, but those people aren't accepting

Stacey Bailey:

the risk or the reward of being that entrepreneurial, because

Stacey Bailey:

they work for you, right? So what we find is that the biggest

Stacey Bailey:

trick is getting these leaders to be really clear about

Stacey Bailey:

expectations and about what they actually want, because they just

Stacey Bailey:

go and do and they don't know how to communicate.

Scott Ritzheimer:

Yeah, yeah. Yeah. I think it's a

Scott Ritzheimer:

particularly big challenge in spaces like creative agencies,

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because the the barriers to entry are so low that anyone who

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is kind of even close to thinking about one day starting

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their own like they'll just go and do it, or at least give it a

Scott Ritzheimer:

shot. And so what that means is you have a lot of people who who

Scott Ritzheimer:

have the opportunity to do it and choose to work for someone

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else instead. That's very, very telling. And, and so you have,

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you know, this group who can do it on their own, want to do it

Scott Ritzheimer:

on their own, love doing it on their own, who've brought in a

Scott Ritzheimer:

bunch of people who don't want to do it on their own. And, and

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it feels like we're talking at each other, even past each

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other. How have you found founders in that place? How can

Scott Ritzheimer:

they start to change the way that they communicate, to bring

Scott Ritzheimer:

the best out of their people?

Stacey Bailey:

It all starts with actually having a vision,

Stacey Bailey:

right? Like a lot of these founders come in and they are

Stacey Bailey:

creating lifestyle businesses, which is great, right? Like

Stacey Bailey:

they're great at their craft. They've got enough clients to

Stacey Bailey:

support their the amount of money that they want to make,

Stacey Bailey:

and then maybe they get more. And so then they bring in team,

Stacey Bailey:

and then all of a sudden, they have a company that is bigger

Stacey Bailey:

than they ever anticipated. That happens all the time, especially

Stacey Bailey:

in this creative space. So getting founders and their teams

Stacey Bailey:

to get really clear on what is the vision about what are we

Stacey Bailey:

doing here? Why are we doing this? Are we trying to create a

Stacey Bailey:

lifestyle business? Are we trying to scale this business?

Stacey Bailey:

Do we want to be the best at what right? Once we can get

Stacey Bailey:

really clear on that, everything else tends to start to fall into

Stacey Bailey:

place where then you start to see all of the players on the

Stacey Bailey:

board and what their unique geniuses are, and how it ladders

Stacey Bailey:

up, but that tends to be the pivot point between everyone

Stacey Bailey:

being in a raft, kind of rowing in opposite directions, and

Stacey Bailey:

creating struggle and strife to let's all be in the same boat,

Stacey Bailey:

in the same direction, paddling with each other. And it's all

Stacey Bailey:

goes down to that vision first.

Scott Ritzheimer:

Are there right and wrong visions?

Stacey Bailey:

Oh, great question. I think that a vision

Stacey Bailey:

is only as good as everyone's commitment to it. So if you set

Stacey Bailey:

a vision that your team is not about, then it's not going to

Stacey Bailey:

work, and you're either going to need to get a new team or a new

Stacey Bailey:

vision. But as long as the vision is something that the

Stacey Bailey:

founder believes in and can buy into and can galvanize the rest

Stacey Bailey:

of the squad around. I think that anything like that is worth

Stacey Bailey:

pushing things forward, and a vision can be reset and recast.

Scott Ritzheimer:

Yeah, yeah, it's so true. So one of the

Scott Ritzheimer:

things that's interested me, we've actually met before, which

Scott Ritzheimer:

is a lot of fun. I don't get to meet a lot of my guests before

Scott Ritzheimer:

we we chat, but dare to lead, and the certification that Brene

Scott Ritzheimer:

and her team have put together is fantastic. How do you bring

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that into this entrepreneurial space?

Stacey Bailey:

So we find that leadership teams, or newly

Stacey Bailey:

forming leadership teams, if they don't exist yet, they tend

Stacey Bailey:

to have a lot of trust issues. They wouldn't describe it that

Stacey Bailey:

way. They would say, we trust each other to get the work done,

Stacey Bailey:

or we trust each other if there was an emergency to have each

Stacey Bailey:

other's back, right? But the way that Brene Brown's dare to lead

Stacey Bailey:

breaks down the elements of trust around this braving

Stacey Bailey:

acronym, around boundaries and reliability and all these

Stacey Bailey:

things. Once we really break that down, people go, oh yeah,

Stacey Bailey:

we've got, we've got some trust issues, right? And that goes

Stacey Bailey:

back to Patrick lencionis, five dysfunctions of a team, you

Stacey Bailey:

know? And so a lot of it is around trust, communication,

Stacey Bailey:

vulnerability and leadership. And in these creative

Stacey Bailey:

businesses, you have a lot of people who are actually pretty

Stacey Bailey:

vulnerable, because creatives tend to have a lot more exposed

Stacey Bailey:

feelings,

Scott Ritzheimer:

yeah?

Stacey Bailey:

Then you know, more technical folks, and that's

Stacey Bailey:

great, but we have to, like, surface those, name those, work

Stacey Bailey:

through those. So we use, you know, dare to lead training to

Stacey Bailey:

help leadership teams develop the trust, the language and the

Stacey Bailey:

communication to really build on so that all of the strategic

Stacey Bailey:

planning work can actually be accomplished.

Scott Ritzheimer:

You said that they lack trust, but wouldn't

Scott Ritzheimer:

call it that. What do they call it? What are some of the

Scott Ritzheimer:

symptoms of a team that's lacking trust?

Stacey Bailey:

So, you know, often they will say, Well, we,

Stacey Bailey:

you know, we're, everybody's working hard, but we're not

Stacey Bailey:

getting it done. It's like, okay, well, that tends to come

Stacey Bailey:

back to like trust, but they are like, I trust that they're

Stacey Bailey:

working hard, right? So they're not labeling it that way. Or

Stacey Bailey:

it's that we disagree and we can't come up with how to agree,

Stacey Bailey:

or I don't feel comfortable saying the hard truth to the

Stacey Bailey:

founder, even though it's holding us all back, right? So

Stacey Bailey:

sometimes they actually think of it as like I'm being respectful,

Stacey Bailey:

because I'm and I'm being nice, but I'm not being kind. I'm not

Stacey Bailey:

saying what needs to be said so that we can be a team that is

Stacey Bailey:

fully functioning in our truth.

Scott Ritzheimer:

Yeah, it almost sounds like you're saying

Scott Ritzheimer:

that not being that being nice could actually take tear down

Scott Ritzheimer:

Trust, which is probably breaking a few people's minds at

Scott Ritzheimer:

the moment. So walk us through, how does that happen?

Stacey Bailey:

So Brene Brown talks a lot about being kind,

Stacey Bailey:

not being nice, and so the way that I like to tell that story

Stacey Bailey:

is nice is, Scott, you have something in your teeth, and I'm

Stacey Bailey:

not going to tell you because I don't want you to feel

Stacey Bailey:

uncomfortable. But being kind is telling you you have something

Stacey Bailey:

in your teeth so that you don't look like a fool as you're

Stacey Bailey:

walking around, right? And I my interest in being nice is

Stacey Bailey:

actually for my own benefit, because I don't want to sit in

Stacey Bailey:

that discomfort versus kindness as being okay with the other

Stacey Bailey:

people having whatever feelings they're going to have, but you

Stacey Bailey:

have to say the truth so that we can all know what's going on.

Scott Ritzheimer:

Yeah. And I think you nailed one of the key

Scott Ritzheimer:

tensions around why this is such a particular challenge in the

Scott Ritzheimer:

creative space, is that sometimes, if it's objective,

Scott Ritzheimer:

you have something in your teeth, but it's like that ad,

Scott Ritzheimer:

that art, that copy, that whatever, that's a little more

Scott Ritzheimer:

subjective and and what I've found is. Oftentimes when folks

Scott Ritzheimer:

are really good at something, they may be very good at

Scott Ritzheimer:

themselves, but not really able to articulate how to get there

Scott Ritzheimer:

or why. How do you help folks that are high performers in

Scott Ritzheimer:

their own right start to overcome that and actually turn

Scott Ritzheimer:

it into a strength?

Stacey Bailey:

Man, feedback is something that we do not

Stacey Bailey:

practice right. Feedback is something it's a skill. It's its

Stacey Bailey:

own sort of art form. And you know, creatives who went to art

Stacey Bailey:

school got a lot of practice and feedback, giving critiques and

Stacey Bailey:

that, and they they, some of them have deep scars from it,

Stacey Bailey:

yeah, but when we get into the professional workplace, we just

Stacey Bailey:

don't get feedback in the same way. So that's something that we

Stacey Bailey:

work with folks a lot is thinking about feedback as a

Stacey Bailey:

gift, truly about how we think about giving people, you know,

Stacey Bailey:

in the moment, bad news best served, hot kind of feedback so

Stacey Bailey:

that we're not letting things linger and fester and we can

Stacey Bailey:

actually grow and develop it. So one of the things I love to

Stacey Bailey:

coach people, to do is to actually build it into their one

Stacey Bailey:

on ones. If they're a manager, it's like, I'm going to give you

Stacey Bailey:

feedback every one on one, and I want you to come and give me

Stacey Bailey:

feedback as your manager every one on one, because then we're

Stacey Bailey:

building a muscle of feedback. But that tends to be the weakest

Stacey Bailey:

part. People just don't give feedback because they want to be

Stacey Bailey:

nice. They don't want to hurt anybody's feelings, but then no

Stacey Bailey:

one's elevating.

Scott Ritzheimer:

Yeah, one of the things that starts to take

Scott Ritzheimer:

shape at this level is that the There are formal team settings,

Scott Ritzheimer:

and then there are individual settings, and those start to

Scott Ritzheimer:

become increasingly separate when it comes to something like

Scott Ritzheimer:

feedback, or some of the trust conversations we talked about

Scott Ritzheimer:

earlier, how can a leader navigate which which forum to do

Scott Ritzheimer:

it in? How do you know if it's a one on one conversation or a

Scott Ritzheimer:

team conversation?

Stacey Bailey:

I think anything that is going to elevate the

Stacey Bailey:

group should be given in the group setting, especially if

Stacey Bailey:

it's positive feedback that you're reinforcing, positive

Stacey Bailey:

behavior, positive outcomes that you want to keep seeing that

Stacey Bailey:

should always be in the group. If it's constructive or

Stacey Bailey:

sensitive or based on what you know about the person you're

Stacey Bailey:

giving feedback to, you think that they will receive it better

Stacey Bailey:

in that one on one setting, then you should always do do that. We

Stacey Bailey:

never want anyone to feel attacked, nor do we want to

Stacey Bailey:

build shame. Brene Brown talks a lot about shame as she is this

Stacey Bailey:

shame researcher, right? So a lot of that dare to lead is

Stacey Bailey:

around lowering our shame shields and our armor that build

Stacey Bailey:

up at work. And so when we get feedback, we have to be

Stacey Bailey:

conscientious of that, because we don't want people to armor up

Stacey Bailey:

and then they don't receive it. So anything that's going to feel

Stacey Bailey:

sensitive should be one on one. Anything that is elevating the

Stacey Bailey:

group should be in the group setting.

Scott Ritzheimer:

Yeah, that's really good. That's really good.

Scott Ritzheimer:

Stacy. There's a question that I have for you, and I want to make

Scott Ritzheimer:

sure after this week, we let folks know how they can get in

Scott Ritzheimer:

touch with you for more help. But before we get there, the

Scott Ritzheimer:

question is this, ask all my guests what, what is the biggest

Scott Ritzheimer:

secret you wish wasn't a secret at all. What's that one thing

Scott Ritzheimer:

you wish everybody watching or listening today knew

Stacey Bailey:

as a leader, you do not need to have all the

Stacey Bailey:

answers. You don't even need to have half of the answers. You

Stacey Bailey:

need to provide clarity and kindness and help them. Them

Stacey Bailey:

being your team, or the people you're working with, come to

Stacey Bailey:

those conclusions themselves. I work with a lot of leaders who

Stacey Bailey:

are like, but I don't know the answers, and it makes me feel

Stacey Bailey:

less than like, I'm not equipped. It's like, but as

Stacey Bailey:

leaders, the best leaders don't know all of the answers they

Stacey Bailey:

have the team. Help them reveal the answers.

Scott Ritzheimer:

Yeah, yeah. It's, it's, it's interesting the

Scott Ritzheimer:

whole arc of that, because you go from doing everything

Scott Ritzheimer:

yourself, being everything yourself, having a couple of

Scott Ritzheimer:

helpers around you, to not even knowing everything yourself,

Scott Ritzheimer:

there's a lot of vulnerability in that, in and of itself. And

Scott Ritzheimer:

this isn't something that comes naturally. This I found for most

Scott Ritzheimer:

founders that, you know, most of us don't just kind of come out

Scott Ritzheimer:

of the gate, you know, ready to lead in this way. And you know,

Scott Ritzheimer:

vast majority of founders would benefit from someone walking

Scott Ritzheimer:

alongside them. Tell us, how can folks find more out about the

Scott Ritzheimer:

work that you do? Where can they connect with you?

Stacey Bailey:

Absolutely. You can find us online at

Stacey Bailey:

intentioncollective.co, or you can email me at Stacey, S, T, A,

Stacey Bailey:

C, E, y, at intention collective.co, we work alongside

Stacey Bailey:

founders and leadership teams to go from being founder led to

Stacey Bailey:

leadership team led, and to scale from that. You know, what

Stacey Bailey:

got us here isn't going to get us there in that next pivot

Stacey Bailey:

point, especially in the creative space. And, you know, I

Stacey Bailey:

don't want to hit the AI, you know, buzzword of the day. But

Stacey Bailey:

with AI, I feel like this work is becoming even more critical,

Stacey Bailey:

because leadership and clarity is going to become sort of the

Stacey Bailey:

essence of what gets you to move forward.

Scott Ritzheimer:

So good, so good. Stacey, it was just

Scott Ritzheimer:

fantastic having you on. Great to see you again as well. Thanks

Scott Ritzheimer:

so much for coming and sharing. In with us some fantastic

Scott Ritzheimer:

thoughts. I absolutely love this conversation, and for those of

Scott Ritzheimer:

you watching and listening, you know your time and attention

Scott Ritzheimer:

mean the world to us, I hope you got as much out of this

Scott Ritzheimer:

conversation as I know I did, and I cannot wait to see you

Scott Ritzheimer:

next time. Take care.

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