Haley Dagan: How to overcome the challenge of letting go to build a team

Small But Mighty Agency Podcast

Episode 62: How to overcome the challenge of letting go to build a team

Speakers: Audrey Joy Kwan, Haley Dagan

Audrey Joy Kwan 

Have you hit a wall in your business struggling to grow from solopreneur. It’s a lean team that can give you back more time. You’re not alone. It’s a common struggle. Building a team for your service business goes beyond hiring people. It’s about creating an effective organizational structure, developing processes, improving communications and stepping into leadership. Today, we’re exploring one challenge that shows up at many stages of business growth. It’s the challenge of learning to let go and give up some control. So, you can step into your leadership role, stay tuned.

Audrey Joy Kwan

Welcome to the Small But Mighty Agency Podcast. If you’re a marketer or consultant, or a creative on a journey of growth from solopreneur to agency owner, follow along because I pull back the curtains on the realities of growing and running a scalable, service-based business and building lean team. I’m your host, Audrey Joy Kwan, I know what it takes to build an agency, whether it’s from solo to three, five or twenty. I’ve done it, including supporting an agency owner to sell and exit. I’ve coached and consulted over 120 marketers, creatives, and consultants. And I’ve been behind the scenes of seven figure businesses. I also have a master’s degree in communications specializing in organizational development. All this to say, I know what it takes to grow lead and operate a multiple six, and seven figure small but mighty agency. And here on this podcast is where we’ll dive right in.

Audrey Joy Kwan

Friends. Welcome back to our little corner of the world today. Our podcast explores what it takes to go from solo to CEO to grow your marketing and consultant business, from solo to CEO, you’re going across different stages and milestones on your journey. One of those milestones is learning to lead others. So much of growing our business is a self-development journey of developing ourselves. Today, we’re talking to Haley about growing her business with the agency model, learning to let go and how she’s stepping into the leadership role. Before we dig in. Haley, tell us about you and how you started your agency.

Haley Dagan

I love this topic. You know, in talking to you about leadership, I think that it’s just so great, especially when you’re starting out and you do have that small but mighty agency mindset. And for me, you know, I actually always thought I would work in corporate America, like if someone was like, oh, what’s your dream career? For me, it was, you know, becoming the CMO at a big company. I worked in hospitality for a long time. So, I thought that was just my career path. And I was I was happy with it. For me, the reality check came in 2020 like many other people working in corporate America, when I lost my job for the pandemic, I’ve been working full time for W hotels, at one of the properties down here in South Florida. And unfortunately, the hotel closed. And you know, when I first took all my work home with me, I thought I’ll be working home from a few weeks. And then when the hotel closed, pretty much everyone lost their jobs. And it really forced me to reevaluate what does, you know, my career and my life look like moving forward? I had just had my, my oldest son turned one. So, it did give me some time to really like be home and kind of be in the moment and decide what my future path would look like. And the Written World was actually an LLC that I started in 2018. So, it started off as my passion project. I always loved being busy, I would come home from work and want to do more work, which I know sounds weird, but I guess just is a natural fit that I ended up being an agency owner. But you know, when I had started it, I really was just taking on a few side projects, I was blogging and doing some content marketing for small clients. And I decided, you know, after a few months when it looked like okay, this, this position isn’t coming back anytime soon. Let me just see what happens. Let me take a chance and just launch it. And my intention was really to be a freelancer. And my intention was just to you know, help some other small businesses with their marketing needs, mostly content and copywriting. And all of a sudden, it kind of took on a life of its own. And I laugh because I actually brought on my first member of my team in May of 2021. So really started the momentum lead in 2020. By May of 2021. I was at the point where I  couldn’t keep saying no to all the projects and B was about to have my second baby. So that’s when I first brought on my first team member and then from there, we just continued to grow. We brought on you know lots of different retainer clients and monthly recurring services. And as I got more retainers, I had to bring on more team members and that’s where I am today.

Audrey Joy Kwan

The picture you painted of a journey resonates with so many service providers. Typically, you get started as a freelancer bumped up against capacity and don’t have enough bandwidth to grow the business. That’s when you need to think about developing a team. People get stuck in self employment because building a team isn’t just about hiring people, it’s about organizational structure, processes, communication, and leadership. So, on the topic of a team, let’s share what your team looks like today.

Haley Dagan

Yeah, so I have two full time employees, I have two-part timers. And then I have a few different contractors that we’ve worked with most have been on board with us anywhere from, you know, six months to two years. And we, you know, we consider them part of our team as well.

Audrey Joy

When we transition from solo to leading people growth happens, both come from meeting challenges head on. So, share what you think was your biggest challenge.

Haley Dagan 

Absolutely. So, I think my biggest challenge has always been letting go. And not just because oh, I’m a perfectionist, or I have a certain way that I like things. But I also feel so personally invested in all of our clients, especially starting as a freelancer. And a lot of those clients that started with me as a freelancer, they’re now you know, on boarded into the agency, and they have an account manager and my team works with them on a daily basis. But for me, it was really just it was letting go and understanding that the only way to grow is to be able to lean on other people within your growth. So, you know, that was a huge challenge and knowing when to kind of start outsourcing. And when you know, there were things that I could no longer do myself. And at what point do I bring on another team member? At what point do I bring on the support that I need? or at what point do I outsource to another partner. So, for me, that was always the biggest challenge and even the empowering others, wanting to make sure that my team feels like it’s okay to make a mistake, I always say make all the mistakes in the world, just don’t make the same mistake twice. But you know, for me really understanding like what it takes to empower someone, and to just be able to let go,

Audrey Joy

let’s go deeper into the challenge of letting go. The first hire supporting client delivery is where the challenge surfaces, letting go of administrative things feels more effortless, but client delivery always feels heavier. What were some of the things you had to work through in your mind to let go?

Haley Dagan 

When I started, the first person that I brought on board was someone who I actually knew very, very well from working in, you know, my past career. So, the first person I brought on with someone that I really trusted. And when I looked at what I was working on, and why I was getting to a point of having to either turn down business or say you know, I have a wait list, I took a look at all the tasks that I was doing every day. And all of those things that I knew didn’t need me like the administrative or some of the bookkeeping, or all that kind of stuff that was like my first part of letting go was okay, I don’t need to do all of this. I don’t need to do all the CRM management and things like that. So, the first person I brought on took care of those tasks for me. But as I continued to grow and get more referrals and get more business, the next part of letting go for me was the hard stuff was the creativity, you know, being a copywriting and content writing agency, so much of what we do is subjective, right? Like, you need to be able to communicate as your client were embodying our client, whether it was a solopreneur, or it was an agency owner, or we were supporting a small business, we become those people. So, you know, that writing part that for me, I was like, how am I ever going to be able to bring on more business and turn this over to others? Especially because I had such a personal relationship with our clients.

Audrey Joy Kwan

I’ve shared this before, the concerns you highlighted are common. But hearing how one person overcomes a shared struggle shows that if you’re struggling with the same thing, there is a way through. Yes, I do think there is a heavy lift when getting client delivery off the plate over administrative things. But it sets us up to get account management and then strategy off your plate. Share more about your first hire and the tools that supported their success.

Haley Dagan 

Yeah, so my first foray was bringing on a freelancer. And really what I did was, I looked at it like what did I need to produce really good content? And for me, it was all about that content brief. It was knowing what I needed to say how I needed to say it, what words what keywords, because everything we do is SEO optimized, like what keywords did I need to have? What types of sources were important to the client? So, I really looked at it like what did I need to do my job really well? And then how can I set up whoever I’m going to bring on really well, too? And so, when I brought on that first freelancer, it was exactly that. It was creating a process where I gave a very detailed brief where I made sure that that writer had everything that they needed to be able to produce a really well written piece of content.

Audrey Joy Kwan 

Thank you for bringing up the tool you use to facilitate the success. Your tool was the creative brief done in a way that highlighted your priorities, the tools and area people blow past. An SOP or a standard operating procedure isn’t enough. And I drill down on tools, my clients, often we think of bringing on a team, we believe that having an SOP that tells someone how to go from step A to B to C, and so forth is enough. But the magic is in identifying the tools that can help someone else deliver on your secret sauce and get aligned with how you do things.

Haley Dagan 

Absolutely. And I think really, it’s even more important when it’s not something that’s black and white. So, it’s easy to do an SOP. And we have plenty of them now as an agency that are like all the repeatable processes, right? Like everything that you know, okay, this is how a client is going to submit information. This is how they’re going to review the content; this is how we’re going to publish it. Like those are the easy ones, right? But it’s those ones that require you to give up that creative control. So, like going back to that letting go like giving up that creative control was going to be my biggest challenge and my biggest hindrance to growth and to becoming the agency that we are. So, I really needed to look at it and say, Okay, how do I break this down into something that is easy to share, and to also empower whoever it is that I’m bringing on to know that they can use their own lens to really follow the guidelines but create their own pieces of content. So that’s where I started. And then over time, again, I really stuck with those same freelancers. And I, I think my next kind of bottleneck in the next area of letting go was like the editing process, because I was getting the articles from my writer. And then I was spending so much time editing it to make it perfect, to make it just the way that I would turn it over and that again became another hindrance, right? Because as you bring on more clients, I’m doing the writing, I now have a writer who’s doing some of the writing too. But now I’m adding editing to my plate. So, kind of those more responsibilities that you add, again, it goes back to okay, how can I grow? How can I scale like, this is not a repeatable process, like I’m only one person and there’s only so much I can do.

Audrey Joy Kwan 

Yes, let’s talk about how you got editing off your plate. We often think that once we get one thing off our plate, the next thing and the next thing feels easier. But the mind can trick us into making it way more complicated than it is. That wasn’t the case for you, share your thought process.

Haley Dagan 

I need someone to help, you know divide and conquer. So, as we’re writing, as I’m writing, as this new writer’s writing, and I started bringing on more writers as well, I need to funnel all of this these pieces of content to an editor. And I need someone who can not only look and just proofread for grammar and spelling, but who can edit from a structural perspective. So, what I started doing was, I brought on the editor, and I also gave the editor access to the content briefs. So going back to that foundation, for us, not only was it important for the writer to understand the direction and all of those things that were needed to produce a really well performing piece of content. But the editor needed that too. Because if the editor is just looking at this one piece of content in silo, that editor is not going to understand the overall picture or that overall strategy. And that’s when I started to bring in project management tools too. So, I said, okay, now I have the people, how am I going to manage the projects?

Audrey Joy Kwan 

Yes, let’s talk about management. Specifically, let’s chat about people management, fear of managing others might stop someone from scaling a service business with a team, which really is the agency model, having a team to support your service delivery, what was your mindset?

Haley Dagan 

So, I think it goes back to realizing that you are never going to duplicate yourself. So, I had this perspective that, you know, this is the way I love to do things. And I know the clients love the way that I’m doing these things because they continue to, you know, pay the monthly retainer and continue to renew the contracts. So, I had it in my head, like this is really the way I want things to happen. And then you realize, like, if I spent all this time trying to clone myself, I’m just going to fail. And I realized that, you know, everyone has their strengths, and everyone has their own unique ways of doing things. And just because I do certain things doesn’t mean that that’s the best way to do them. And I actually I credit this to my brother who’s happens to be younger than me but is very wise. And he made the comment to me, I was talking about, you know, these growing pains and, um, how much time that I have to spend, you know, looking over everything and how, you know, OCD maybe that I am to make sure that it checks all of my boxes. And he said to me, have you ever turned over a piece of content, you know, a written and edited piece of content directly to your clients? And I said, No. And he said, Well, why not? And I said, well, because I need to make sure that you know it follows this. And he said, but you don’t know like maybe you would turn over that piece of client content and your client would love it. You don’t know because you’ve never given them the opportunity. And I just was like, you know what, it’s very true. And I decided it was time to try that.

Audrey Joy Kwan 

Whether you’re a creative consultant or marketer, you’re more than likely very particular about how you want things done. And it’s difficult to see how someone else can come in to support the creative work and be good enough, the thing is, nobody is going to do something exactly like you. But it doesn’t mean it isn’t good enough. Coming to that realization allows you to determine what is good enough and grow the business, you’re on the journey of building your mighty pod team, you’ve got client delivery taken care of by specialists, now you’re building up your account manager, tell us how that’s going.

Haley Dagan 

So that VA that I had brought on, like very early on, you know, back in May of 2021, I started to give more and more responsibility. So, as I learned to let go in some of the creative processes, I also learned to let go in the client communications. And I really gave her the opportunity to start interacting with clients, to be on the client calls. And then I started realizing I can’t always be on every single client touch base, or every single email. And I started to turn those over. So, she really grew from, you know, managing my daily tasks as a VA to that account manager position. And she’s continued to grow with us as well. But for me, I was really able to kind of use that opportunity of having someone that okay, now she’s been in my business, she’s been in my business and seen all my processes, she sees the way I’m interacting with clients, she’s copied on emails, and I started to really empower her to take over those conversations, and to be able to be that account manager for us.

Audrey Joy Kwan 

It gets real and team members are excited to grow with us and take on more responsibility. If you have a VA or someone in your business, what the natural strengths to become an account manager, we want to support them, it doesn’t always work out that way because not all VAs want or have natural giftings that lead them into the account manager role. I know agency owners want to find great account managers when building an agency. Thanks for sharing how you gained your first account manager. Okay, now that you have a team to support the implementation and account management, what is one key learning you would share with others?

Haley Dagan 

Yeah, I think that the biggest thing for me was just allowing people the ability to feel like it’s okay to make mistakes. And I think, you know, like I said earlier, you can make all the mistakes in the world, just don’t make the same mistake twice. And I think really getting that point across to my team, because in the beginning, it was like, hey, is it okay? If I send this email, or, hey, the client didn’t get back to me. And you know, they were supposed to get back to us within seven days, is it okay, if I follow up. And I realized after a while, like, I must be kind of making my people feel like they can’t go out there and just do what they need to do, or just speak to the client or pick up the phone and call them because I see that they’re really trying to filter everything for my approval. So, I really had to look within and realize that you need to, as a leader, tell your team that it’s okay to just feel empowered, and go ahead and if you make a mistake, we’ll fix it. We’re not in surgery, like we’re not going to alter someone’s life if a piece of content goes out when it’s not supposed to. It’s not the end of the world. And I think also as you grow as an agency, you realize that, you know, if a client is going to be really angry, or unreasonable, because your team makes a mistake, they’re probably not the right client for you. And I think once I had that mindset myself, and I was able to start really communicating that to my team, I think that really like the ball just started rolling forward so much faster, because my team felt they can get what’s done what they need to get done, they can speak to the clients. And we can just keep propelling and pushing out that content like we need to.

Audrey Joy Kwan 

The analogy that it’s not surgery is a powerful reminder that mistakes are not life and death and can be used for good in your business. In particular, when you bring in a new hire, the purpose of onboarding and training is to allow them to make mistakes, and then of course, correct for learning. So, before we wrap up, is there anything else you want to share about your journey to building your agency?

Haley Dagan 

Yeah, I mean, I think that just having that mindset that you don’t know until you try, I think that so much of owning an agency is trial and error. And sometimes like it’s never going to be perfect. Sometimes I look back and I’m like, oh, I wish that we started you know, these processes sooner, or I wish that we really were able to, you know, get this software on boarded earlier on in the agency or things like that. But I think that just being able to know like we said, it’s okay to make a mistake, and you’re going to make mistakes along the way and just embracing the fact that you need to try something until you know it doesn’t work. And I think that for me that’s been such a huge part of being able to grow the agency to where it is today. And even this year. In 2022 for us, we had so much momentum with clients. We had so much momentum in our processes, and we started automations, and we started really like building out the back end of the business. And for me 2023 is like all about just growth and propelling us forward. And we brought on our first two full-time employees this year because of that and I think knowing that it was okay to learn, to try new things, some things didn’t work, you know, people, people might not work either. And being able to just realize that the only way to kind of move forward and grow is to try new things.

Audrey Joy Kwan 

If you create a complex business that makes you feel trapped, you will never want to grow your business, you’ll do little or big things to self-sabotage growth, because nobody wants to scale overwhelm, not you, not me, I’ve been there, I learned this lesson as a second in command of an agency, I could not turn off my brain and relax because I would worry about what was and wasn’t being done. It wasn’t until I looked at the business productized service perspective, it gave us more bandwidth to double the revenue and sell an exit the business. Since then, I’ve been behind the scenes on multiple six and seven figure service-based businesses, helping consultants and marketers who are at capacity to get out of being stuck in service delivery and growing, it all starts by looking through the lens of a productized service, download the free productize your service roadmap, go to audreyjoykwan.com/roadmap, or click the link directly in your show notes.

Audrey Joy Kwan 

Okay, speaking of trying new things, you’re going into a brick and mortar office, that is so different from many of my fully remote clients, who want to stay remote, what’s inspiring your decision, give us the details.

Haley Dagan

So, I mean, I fully believe that people can work remotely and be productive. So, it’s not that but I also believe in the power of collaboration, in person connections, and teamwork. And I think that a lot of that is lost when you work remotely. And, you know, obviously, I love the flexibility too, right? Like, I’m now a mom of three kids like four and under. So, I have crazy schedules sometimes. So, I love the flexibility to and that’s why I’ve built this business. But I also miss that in person connection, that in person collaboration. And I know my team does too. So, it started with, hey, like who wants to work in person, let’s meet at a coffee shop. And I started to look for people as I grew, I started to look for people who were local, or who were in South Florida or, you know, within driving distance, we do have one member of our team who is out of state, but everyone else is in state and mostly close to me in South Florida. So, it started with the hey, like let’s meet at a coffee shop, and let’s work together for a few hours. And then I started you know, for me too, it’s like, I’m not as productive at home all the time. Like, there’s definitely times where, okay, I put my head down, I you know, turn on my focus music and I get my work done. But I have a lot of distractions at home to the kitchen, my kids, the gardeners who are coming and mowing a lawn in the middle of a call. And you know, for me, I started with just going into a co working space, but even then it’s like you miss that like, okay, let’s just go somewhere together. It’s almost like, you know, you go you go to the library, when you’re in college, and like you’re more productive, because there’s other people around you who are working, even though everyone’s silent. So, I wanted to have a place really for my team where we can come, we can collaborate, but we can also be all together and just put our heads down and work and just say like, okay, we’re gonna come into this space, and like, we all have a huge to do list, like, let’s be productive, let’s motivate each other. Let’s get this done. And then if we need to, we have conference space, we can step out into the conference room, we can actually invite clients, we have a lot of local clients here in South Florida who can come in and like have a meeting with us in person, and we don’t all just need to be tiny, you know, squares on a Zoom screen or, you know, Teams we use internally, but we can actually come together and collaborate. So, for me, that’s really what’s been behind the decision to find an office space and a place that we can all come in and be together, work together, and, you know, just continue to grow. And it’s funny, because, you know, in this evolution of our agency, like company culture was not something that I really thought about, I was never like, okay, this is the type of culture I want to build, but just to see that kind of build itself and take on a life of its own. And, you know, we have within our Microsoft Teams, a team shout out and to see the people within the team calling each other out when they got great feedback from a client or somebody helps someone else solve a problem, you know, being able to see that evolve without me, or being able to see that there’s inside jokes going on the team that I’m not involved with, like, I’m so proud of that. And you know, for me, the more that I can do to help my team build that culture to feel that, you know, closeness to connect with clients, the more that I want to do for them. So that’s why you know, this office, finding a brick and mortar, finding an office space has been such a priority for me, and I’m excited that we can do it.

Audrey Joy Kwan 

Despite what most agencies small agencies are doing right now, which is going remote or staying remote, you’re going against that grain, you’re planting your flag and living out your values of collaboration in a way that’s so authentic to you. So, I just want to say that’s exciting to hear you stay true to those values.

Haley Dagan 

Thank you.

Audrey Joy Kwan 

Haley. Our last question, tell us what keeps you inspired and motivated?

Haley Dagan 

That’s such a great question. Honestly, it’s my team. And it’s my clients. Just seeing the work that gets done, seeing the results like seeing how proud the team feels when they finally turn over a big project or we see our clients launch their website, we see those analytics reports coming in. Like it’s really, it’s my team, it’s my clients that just keep me motivated to keep going. It makes me want to keep doing more of this. And like I said, at the very beginning of our conversation, like I never thought I would be a business owner.

Audrey Joy Kwan 

Thanks, Haley, where can people find you?

Haley Dagan 

Our website, of course, the writtenworldagency.com. And then we spent a lot of time Instagram has been a great channel for us. We build amazing community there. So, we’re at the writtenworld on Instagram and pretty much every social media channel, but you know, feel free. I also have my own founder account at Haley’s written worlds.

Audrey Joy Kwan 

Thank you so much. Haley.

Haley Dagan 

Thank you. Thank you for having me.

Audrey Joy Kwan 

Hey, there. Thanks for hanging out with me at the small but mighty agency podcast. If you enjoyed this episode, it would mean the world to me if you hit the follow or subscribe button in your podcast app and share it with a friend and I’ll see you in the next one.