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:
– What it takes to build real trust and give effective feedback instead of being “nice”
– 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
Episode Transcript
Scott Ritzheimer
Hello, hello and welcome. Welcome once again to the start, scale and succeed. Podcast, the only podcast that grows with you through all seven stages of your journey as a founder, I’m your host, Scott Ritzheimer, and today’s episode centers on all those high achieving founders out there, creatives, dreamers, visionaries and the like, who are really good at what they do. You know who I’m talking about? You know, if this is you like you just crush it. And as the team around you starts to grow, as you start bringing more people into the fold, the problem starts to pop up that it just seems like no one else can keep up. They don’t think like you, they don’t act like you, they don’t make decisions like you. They don’t work the hours that you do. And all of this starts to grow, and as the organization gets bigger, so does the frustration of trying to keep everyone moving in the same direction. Now here’s the bad news, that the very thing that made you successful is also the very thing that’s likely to sabotage you at this level, as a leader, you can’t out craft your way through a people problem, and most creative founders learn that the hard way. But the good news is that Stacey Bailey is here with us today.
Stacy is a leadership coach, strategist and facilitator who helps entrepreneurs and creative leaders to build businesses with heart. She’s a system and soul implementer and a dare to lead certified professional who brings more than 15 years of experience in leadership and operations within the creative services industry today, through the intention collective Stacy partners with founders and leadership teams of creative agencies generating one to 15 million 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. Stacy, welcome to the show. Glad to have you here. Would love to just dive in right out of the gate creative agent. You work a lot in the creative agency space, and I have found that this level is particularly hard for folks like that. They’ve they’ve hired their first handful of people, and there it’s something not right. What’s going on here?
Stacey Bailey
Well, thanks for having me, Scott. You know, usually these folks got into their roles because they were great at their craft. And then, you know, we get more people in, and they are like, Why can’t these people do this the way that I do this? And usually they’ve elevated themselves into a little bit of a pickle, right? So what we tend to find is that we’ve got founders who are makers, and they go, I can’t take it all. I’ve been doing all of it for too long, and I’m exhausted. But now I don’t quite know how to convey clearly what good looks like, what excellent looks like, how I want these people to elevate in their craft, so that I can let go of the reins a little bit.
Scott Ritzheimer
Yeah, I think one of the things that makes this hard is that for high performers who have the style, makeup, guts to go out and start their own thing with all the risk that comes with that, they tend to also be the type of folks who don’t really like to be managed a whole lot and and so one of the things that I think they do is impose that view on others as well. Do you see that happening in the creative space?
Stacey Bailey
Absolutely, these people started businesses because they didn’t want to work for someone else, right? And they then they are saying, well, you need to go and be as entrepreneurial as I am, but those people aren’t accepting the risk or the reward of being that entrepreneurial, because they work for you, right? So what we find is that the biggest trick is getting these leaders to be really clear about expectations and about what they actually want, because they just go and do and they don’t know how to communicate.
Scott Ritzheimer
Yeah, yeah. Yeah. I think it’s a particularly big challenge in spaces like creative agencies, because the the barriers to entry are so low that anyone who is kind of even close to thinking about one day starting their own like they’ll just go and do it, or at least give it a shot. And so what that means is you have a lot of people who who have the opportunity to do it and choose to work for someone else instead. That’s very, very telling. And, and so you have, you know, this group who can do it on their own, want to do it on their own, love doing it on their own, who’ve brought in a bunch of people who don’t want to do it on their own. And, and it feels like we’re talking at each other, even past each other. How have you found founders in that place? How can they start to change the way that they communicate, to bring the best out of their people?
Stacey Bailey
It all starts with actually having a vision, right? Like a lot of these founders come in and they are creating lifestyle businesses, which is great, right? Like they’re great at their craft. They’ve got enough clients to support their the amount of money that they want to make, and then maybe they get more. And so then they bring in team, and then all of a sudden, they have a company that is bigger than they ever anticipated. That happens all the time, especially in this creative space. So getting founders and their teams to get really clear on what is the vision about what are we doing here? Why are we doing this? Are we trying to create a lifestyle business? Are we trying to scale this business? Do we want to be the best at what right? Once we can get really clear on that, everything else tends to start to fall into place where then you start to see all of the players on the board and what their unique geniuses are, and how it ladders up, but that tends to be the pivot point between everyone being in a raft, kind of rowing in opposite directions, and creating struggle and strife to let’s all be in the same boat, in the same direction, paddling with each other. And it’s all goes down to that vision first.
Scott Ritzheimer
Are there right and wrong visions?
Stacey Bailey
Oh, great question. I think that a vision is only as good as everyone’s commitment to it. So if you set a vision that your team is not about, then it’s not going to work, and you’re either going to need to get a new team or a new vision. But as long as the vision is something that the founder believes in and can buy into and can galvanize the rest of the squad around. I think that anything like that is worth pushing things forward, and a vision can be reset and recast.
Scott Ritzheimer
Yeah, yeah, it’s so true. So one of the things that’s interested me, we’ve actually met before, which is a lot of fun. I don’t get to meet a lot of my guests before we we chat, but dare to lead, and the certification that Brene and her team have put together is fantastic. How do you bring that into this entrepreneurial space?
Stacey Bailey
So we find that leadership teams, or newly forming leadership teams, if they don’t exist yet, they tend to have a lot of trust issues. They wouldn’t describe it that way. They would say, we trust each other to get the work done, or we trust each other if there was an emergency to have each other’s back, right? But the way that Brene Brown’s dare to lead breaks down the elements of trust around this braving acronym, around boundaries and reliability and all these things. Once we really break that down, people go, oh yeah, we’ve got, we’ve got some trust issues, right? And that goes back to Patrick lencionis, five dysfunctions of a team, you know? And so a lot of it is around trust, communication, vulnerability and leadership. And in these creative businesses, you have a lot of people who are actually pretty vulnerable, because creatives tend to have a lot more exposed feelings,
Scott Ritzheimer
yeah?
Stacey Bailey
Then you know, more technical folks, and that’s great, but we have to, like, surface those, name those, work through those. So we use, you know, dare to lead training to help leadership teams develop the trust, the language and the communication to really build on so that all of the strategic planning work can actually be accomplished.
Scott Ritzheimer
You said that they lack trust, but wouldn’t call it that. What do they call it? What are some of the symptoms of a team that’s lacking trust?
Stacey Bailey
So, you know, often they will say, Well, we, you know, we’re, everybody’s working hard, but we’re not getting it done. It’s like, okay, well, that tends to come back to like trust, but they are like, I trust that they’re working hard, right? So they’re not labeling it that way. Or it’s that we disagree and we can’t come up with how to agree, or I don’t feel comfortable saying the hard truth to the founder, even though it’s holding us all back, right? So sometimes they actually think of it as like I’m being respectful, because I’m and I’m being nice, but I’m not being kind. I’m not saying what needs to be said so that we can be a team that is fully functioning in our truth.
Scott Ritzheimer
Yeah, it almost sounds like you’re saying that not being that being nice could actually take tear down Trust, which is probably breaking a few people’s minds at the moment. So walk us through, how does that happen?
Stacey Bailey
So Brene Brown talks a lot about being kind, not being nice, and so the way that I like to tell that story is nice is, Scott, you have something in your teeth, and I’m not going to tell you because I don’t want you to feel uncomfortable. But being kind is telling you you have something in your teeth so that you don’t look like a fool as you’re walking around, right? And I my interest in being nice is actually for my own benefit, because I don’t want to sit in that discomfort versus kindness as being okay with the other people having whatever feelings they’re going to have, but you 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 tensions around why this is such a particular challenge in the creative space, is that sometimes, if it’s objective, you have something in your teeth, but it’s like that ad, that art, that copy, that whatever, that’s a little more subjective and and what I’ve found is. Oftentimes when folks are really good at something, they may be very good at themselves, but not really able to articulate how to get there or why. How do you help folks that are high performers in their own right start to overcome that and actually turn it into a strength?
Stacey Bailey
Man, feedback is something that we do not practice right. Feedback is something it’s a skill. It’s its own sort of art form. And you know, creatives who went to art school got a lot of practice and feedback, giving critiques and that, and they they, some of them have deep scars from it, yeah, but when we get into the professional workplace, we just don’t get feedback in the same way. So that’s something that we work with folks a lot is thinking about feedback as a gift, truly about how we think about giving people, you know, in the moment, bad news best served, hot kind of feedback so that we’re not letting things linger and fester and we can actually grow and develop it. So one of the things I love to coach people, to do is to actually build it into their one on ones. If they’re a manager, it’s like, I’m going to give you feedback every one on one, and I want you to come and give me feedback as your manager every one on one, because then we’re building a muscle of feedback. But that tends to be the weakest part. People just don’t give feedback because they want to be nice. They don’t want to hurt anybody’s feelings, but then no one’s elevating.
Scott Ritzheimer
Yeah, one of the things that starts to take shape at this level is that the There are formal team settings, and then there are individual settings, and those start to become increasingly separate when it comes to something like feedback, or some of the trust conversations we talked about earlier, how can a leader navigate which which forum to do it in? How do you know if it’s a one on one conversation or a team conversation?
Stacey Bailey
I think anything that is going to elevate the group should be given in the group setting, especially if it’s positive feedback that you’re reinforcing, positive behavior, positive outcomes that you want to keep seeing that should always be in the group. If it’s constructive or sensitive or based on what you know about the person you’re giving feedback to, you think that they will receive it better in that one on one setting, then you should always do do that. We never want anyone to feel attacked, nor do we want to build shame. Brene Brown talks a lot about shame as she is this shame researcher, right? So a lot of that dare to lead is around lowering our shame shields and our armor that build up at work. And so when we get feedback, we have to be conscientious of that, because we don’t want people to armor up and then they don’t receive it. So anything that’s going to feel sensitive should be one on one. Anything that is elevating the group should be in the group setting.
Scott Ritzheimer
Yeah, that’s really good. That’s really good. Stacy. There’s a question that I have for you, and I want to make sure after this week, we let folks know how they can get in touch with you for more help. But before we get there, the question is this, ask all my guests what, what is the biggest secret you wish wasn’t a secret at all. What’s that one thing you wish everybody watching or listening today knew
Stacey Bailey
As a leader, you do not need to have all the answers. You don’t even need to have half of the answers. You need to provide clarity and kindness and help them. Them being your team, or the people you’re working with, come to those conclusions themselves. I work with a lot of leaders who are like, but I don’t know the answers, and it makes me feel less than like, I’m not equipped. It’s like, but as leaders, the best leaders don’t know all of the answers they have the team. Help them reveal the answers.
Scott Ritzheimer
Yeah, yeah. It’s, it’s, it’s interesting the whole arc of that, because you go from doing everything yourself, being everything yourself, having a couple of helpers around you, to not even knowing everything yourself, there’s a lot of vulnerability in that, in and of itself. And this isn’t something that comes naturally. This I found for most founders that, you know, most of us don’t just kind of come out of the gate, you know, ready to lead in this way. And you know, vast majority of founders would benefit from someone walking alongside them. Tell us, how can folks find more out about the work that you do? Where can they connect with you?
Stacey Bailey
Absolutely. You can find us online at intentioncollective.co, or you can email me at Stacey, S, T, A, C, E, y, at intention collective.co, We work alongside founders and leadership teams to go from being founder led to leadership team led, and to scale from that. You know, what got us here isn’t going to get us there in that next pivot point, especially in the creative space. And, you know, I don’t want to hit the AI, you know, buzzword of the day. But with AI, I feel like this work is becoming even more critical, because leadership and clarity is going to become sort of the essence of what gets you to move forward.
Scott Ritzheimer
So good, so good. Stacey, it was just fantastic having you on. Great to see you again as well. Thanks so much for coming and sharing. In with us some fantastic thoughts. I absolutely love this conversation, and for those of you watching and listening, you know your time and attention mean the world to us, I hope you got as much out of this conversation as I know I did, and I cannot wait to see you next time. Take care.
Contact Stacey Bailey
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 [email protected]
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/