Ep: 116 - What Are You Willing to Do to Stop Playing Small in Business With Gill Moakes (Copy)
In this episode of Scaling Expertise, I sit down with Jillian Dolberry, team and systems strategist and founder of Jillian Dolberry HQ, to talk about what it really takes to scale a business with integrity. Jillian shares why values are the compass for sustainable growth — and how mindset can either fuel or stifle your potential as a business owner.
We get honest about the emotional toll of leadership, the myth of perfect systems, and why grace — not grit — may be your best growth strategy. Plus, Jillian introduces her 90-day intensive, built to help you step into your CEO role with confidence and clarity.
Whether you're building your first team or rethinking your systems to scale, this episode will help you align your operations with what matters most.
Key Takeaways:
Grace Fuels Growth - Jillian shares that giving yourself grace during setbacks is essential to scaling with confidence and authenticity.
Decisions Shape Your Business - Poor delegation and disconnection often stem from reactive decision-making that isn’t grounded in your values.
Delegation Requires Clarity - Understanding your business functions through tools like the Team Task Tracker makes effective delegation possible and scalable.
Mindset Is the Real Obstacle - Many scaling challenges aren’t about resources—they’re about internal beliefs that need to be addressed with awareness, action, and accountability.
Structure Enables Sustainability - Building systems that reflect your values and leadership style is key to running a business that grows without burning you out.
Connect with Erin to learn how to Turn Your Expertise into Scalable Recurring Revenue.
Erin's LinkedIn Page: www.linkedin.com/in/erinaustin/
Scaling Expertise YouTube Page: https://www.youtube.com/@Scalingexpertise
More About Our Guest
Jillian Dolberry
Jillian Dolberry is a coach and business manager for women entrepreneurs, specializing in operations management and creative services. She's known for her work with virtual assistants and online business managers, guiding them on setting boundaries, developing systems, and navigating difficult conversations. Jillian also hosts the Grace-Filled CEO Podcast, further sharing her expertise in business management and leadership.
Find Our Guest
Music credit: Paphos by Mountaineer
A Team Dklutr production
Blog Transcript:
Erin Austin: Hello everyone. Welcome to this week's episode of Scaling Expertise. I am very excited about my guest today, Jillian Dalver, where we will talk about one, how she helps you scale your expertise, and we'll also have a little look behind the scenes to show how she has scaled her expertise. So welcome to Scaling Expertise, Jillian.
Jillian Dolberry: Thank you for having me. I'm excited to be here.
Erin Austin: Yeah, I'm excited as well. I, you know, before we hit record, I let her know that I have had the pleasure of using some of the tools that she uses. So, uh, but before we get into this, Jillian, will you introduce yourself to the audience?
Jillian Dolberry: Of course. So, I'm Jillian Dolberry, and I own an OBM and team strategy company.
Right now we are helping women business owners. Scale sustainably through auditing their leadership team and systems and figuring out where the blind spots are in those areas where we can leverage what they're already doing well and continue to grow in their business. So we really take a holistic approach and how we serve our clients.
And the thing that you were mentioning was our team task tracker, and that's a way that we're able to kind of. Gift someone the opportunity of creating KPIs and selecting what, basically delegating what they wanna give off to somebody on their team. So we love the women that we work with. Um, we typically do like 90 day sprints with them, so we get to have that really intense working time together.
And the growth that we're able to see is incredible. It's really rewarding.
Delegation Starts with Clarity
Erin Austin: Yeah, the, the task manager is so, 'cause it's, you know, for me, overly inclusive, I have a fairly simple business, but it made me think about so many issues. I mean, a lot of us, as we grow our business, obviously many of us start doing everything and then we start.
How do we peel off? How do we peel off? And it really had me thinking about the functions too.
Jillian Dolberry: Mm-hmm. Um,
Erin Austin: because, you know, I have an OBM who does everything, but now that we're starting to grow the team, like, okay, like how do I start to like even specialize in, you know, marketing, you know, operations, other things like that, delivery.
And so it's been really, really helpful for me to think through all the things that are happening in my business that I really, I. Didn't identify by function, honestly. You know, I'm like, oh, that is operations. That, that is, like, I wasn't thinking about it that way. And I imagine you come across that quite a bit.
Jillian Dolberry: Yeah, absolutely. Um, what the, the team task Tracker does is it gives people a list to start with of saying, you know, these are the things that happen in my business every day and. But it shows you who you can delegate them to or even acknowledgement that you're the one doing those and maybe you don't have to be right.
Erin Austin: So important, I'm a huge believer in, uh, the division of labor and um, and I believe in staying in my lane, it's not always possible. 'cause sometimes, you know, you just have to do things that, uh, aren't quite in your lane. But anytime I can spend, you know, kind of developing my expertise instead of figuring out, you know, what.
Just post on social media or things like that is a well spent to have that delegated. Yeah. Alright, so we, we went off track a little bit because I really wanted to start with how you got to where you are. Oh yeah. And talk about more about your expertise.
Jillian Dolberry: Yeah, I appreciate that. So, you know, I actually got my college degree in graphic design.
And really enjoyed that. I'm a very creative person at heart and still really enjoy creative activities and even doing them in my own business, it's a perk, I guess, that I have that experience. But I was in the corporate world and ended up, I. Quitting my job because I just, it was, the corporate culture was just killing me from the inside out.
Mm-hmm. I was just not created for that environment and so I ended up working with a small family business and doing some office management in addition to some marketing type work, and so. When I started that job, I realized that I really loved management. I really loved people. I really loved like building out a culture, coming up with a value system, creating standards for people to abide by, because while that.
Sometimes feels like there's just a lot of rules and regulations. It's actually something that's intended to make people feel secure in their work environment. And so that is when I realized that that was a gift that I had and a passion that I had. Um, I really just took that and ran with it and just maximize it in every way that I could and started doing virtual assistant work and working with female business owners who were growing their own business.
And supporting them in that way. And then moved into more management pieces for those women and have had clients that I've worked with for four plus years, and it was just incredibly rewarding to start in their business somewhere and kind of end in a completely different position, but also be able to witness all that growth that they've had along the way.
Mm-hmm. And so one thing that. Really hits home with me, with every single person that we've worked with, is we all have this desire to run our business. Well make immense impact with the people that we work with, but also have impact within our home and do all of those things in a really, really healthy way.
That's not compromising who we are as people. And so being able to build that out alongside these amazing women business owners has been. Incredible and such a gift to be able to continue to do that. That
Erin Austin: is beautiful. Yeah. I think we forget how much, and this could be a uniquely American thing, I'm not gonna generalize a little bit, but how much of our lives, like, it's very hard to make these clean distinctions between our businesses and our home lives.
Jillian Dolberry: Mm.
Erin Austin: And that we need that structure honestly, to operate among them. Like if something needs to get done by me. Does it matter if it's for my business or for my home? Like it has to get done and has to get done by me. And so, um, to be able to kind of make sure that we have the structures in place to help us do it efficiently is, is fantastic.
Jillian Dolberry: Yeah.
Decisions, Delegation & Self-Compassion
Erin Austin: Now, one of the things I love to ask people is what they think, how they think about scale. Like there's, it's one of those words that I thought. At the beginning was kind of had a universal definition and it turns out it does not at all. And everyone has their own idea about what scale means. What does it mean to you?
Jillian Dolberry: I love that question. I think what it means to me is to
grow more without costing you more. Mm-hmm. Um, and really I think about that from a really positive standpoint. Like when we. We could scale a business and it could cost us even more than money or time or energy. It could cost us a combination of those things. But when I think about scaling and thinking about what that looks like for the women that we work with and for the value system that we hold, it's being able to.
Not have that ceiling of progress or profit or revenue and really just like breaking through that, but doing it in a, in a way that honors who we are as people and the reason why we started the business in the first place.
Erin Austin: Yeah, absolutely. Yeah. I mean, there's some people who will take the position that's scaling.
They make this distinction between growth and scaling, and I personally don't. And that they, that it's a stage versus an activity, and I think it's an activity or even, you know, versus a stage. And so for some people, and, and will you scale more effectively depending on what stage of development you're at?
A a, absolutely. But that we should all be thinking about how. To increase revenue without increasing, um, costs. Like that should be something we should be doing always when we're thinking about it. And, uh, you know, which brings us kind of to the intellectual property question. You know, I obviously think that.
Developing intellectual property assets is a big part of that, but so is structure, so are processes. Tell me how you like work with your clients. Like what are they struggling with when they come to you and how do you know how to steer them?
Jillian Dolberry: Yeah, they struggle with making decisions. Mm-hmm. Delegating and feeling disconnected from their business.
Mm-hmm. And really those three kind of like feed into each other. And the way that I like to visualize it is if you start at, it starts with the way you make decisions in your business, may be reactive, it may be. Urgent. Um, it may just come from a healthy place of feeling like you have to do something, but not necessarily that's fully in alignment.
And once you make that decision, that's just a little bit off, it affects the way that you're able to delegate things. It affects the way that you see yourself and your business and the way that you, um, are able to view being able to. Bring people in to support your business, whether that be that you already have a team or don't have a team.
Mm-hmm. But you feel like you're maybe not there yet. It all starts with that decision process and it like creates these, um, beliefs in our mind that we're just not there, we're just not good enough, or we haven't quite made it to that point yet, or we don't have enough money. There's like something missing and, and it creates this like.
Incorrect belief. Mm-hmm. Then it affects the way that we delegate and then that all turns into feeling disconnected from our business because if we are not making those decisions that are fully aligned and allowing ourselves to stay in that really focused, intentional role, which. In the strategy, it's in the marketing, it's in the reasons why we do what we do, not the things that we could be delegating to people, but the things that only you can do in your business.
Mm-hmm. Which is probably about 20% of what you think you have to do in your business. Right. Um, but that it all leads to feeling disconnected. And then that, to me, just kind of spirals into a cycle of burnout.
Erin Austin: Mm-hmm. So they are feeling like I, I know. I'm doing something wrong, but I just don't know what is that like.
Jillian Dolberry: Yeah. And you know, I feel like with decision making mm-hmm. We all do our best. Mm-hmm. And the majority of the women that I work with have families. They've got sports schedules. They might have another job or another business. Mm-hmm. Um, their husbands work full-time. Their kids are, are always busy and doing things.
They're running a household. Mm-hmm. I mean, we're all spinning a million plates at the same time. And so when. You're probably, we're all doing our best in the way that we make decisions. The advice that I give people is if you pause before you make any decision, you evaluate what's most important to you.
You look at that value system and you have a good idea of where those values come from and what they look like in action in your business. Then it allows you to pause. Take that decision, filter it through those values, and it's probably the decision you make after that is probably gonna be a little bit different than what you would've made if you felt reactive and you felt like it was urgent.
Erin Austin: Mm-hmm. Yeah, I agree. I, I have also seen, you know, well, when you make value-based decisions, you're almost like making one decision. You know, at the values level and then everything else just follow. You don't have to keep making the decision every time. So comes up, makes they work for you.
Jillian Dolberry: Yes, the values make the decisions for you.
That which then almost removes some of the emotional toll that it has on us because we're not having to like, think in, in each, all these individual situations. Instead we just look at the one thing that we already made the decision on. Right. And filter it through that.
Erin Austin: That's right. Yeah. I mean, I have a recent example of a client who, you know, they had a client who was trying to push boundaries about, mm-hmm.
Like, you know, you've made the decision to operate with best practices for your industry. Mm-hmm. So either you're sticking with that or you aren't. Like it's already decisions already made. If you said, no, we're always gonna stick with best practices and not make changes. I mean, it's great. I mean, I know you want the client, but what is going to Trump here, and that's another, you know, best practices, values or whatever, that helps you make all those downstream decisions as well for your clients.
Yeah, yeah, yeah. So tell me about how you have scaled your business.
Jillian Dolberry: I wanna be completely honest with you.
Erin Austin: Please do.
Jillian Dolberry: It is so hard.
Erin Austin: It's,
Jillian Dolberry: it's, and it never feels easy. It when you, when you talk about it and you hear other people talk about it and they're like, here's how you scale your business. I feel like I'm, I'm giving interviews on that left and right right now, and I think the, the thing that nobody tells you is that.
The quickest way to scale your business is to give yourself grace when you screw up. Mm. Because what keeps us small, what keeps us from taking that next bold, courageous step in business is what we believe about ourselves and what we're telling ourselves about what we're doing. Yeah. And so I've never seen anyone.
Fail more or fail harder or not grow for giving themselves more grace and. I really just feel like that starts with us. Yes. It's about giving our team grace. Yes, it's about giving our clients grace. It's about holding those boundaries. I could go on and on and on about all those things, but ultimately we gotta start with us because we have to be kinder.
We have to be kinder to ourselves in those moments. Mm-hmm. I know for myself, I put a lot of pressure on myself. I want it to be perfect. I want it to look professional. I want it to be good, and I want it to be better than good. Let's be real. And, but when I do that, I'm like really holding myself back from showing my true expertise, showing my gift, showing my vo, showing my vulnerability in business.
And really, I feel like that is the secret to success is just being who you are and allowing those gifts of what's been planted into you to shine and overflow out of you. And you can't do that when they're being stifled down by negative beliefs and incorrect like. Beliefs and mindsets around who you are.
Erin Austin: I will tell you, like since, you know, I've been kind of, my podcast was on hold for six months and just started back in the new year, and the number of women who talk about mindset like, which is not that I don't, you know, my little too legal minded. It's not that I don't think about mindset, but like everyone, like how important mindset is.
Yeah. And the thing that can be holding us back, not. The market, not our, you know, ip, not our systems, but our mindset Yeah. Is surprisingly important. And I, you know, and I always ask frankly, if we think, you know, when you work with women, do we think this is unique to women? Um, you know, because we maybe have a little bit more of a perfectionist mindset.
Jillian Dolberry: Yeah. I mean maybe I, I really feel like there's everything that's happened in our lives up until this point is playing into how we're running our businesses today. Mm-hmm. I would love to sit here and, and say that I compartmentalize those things, but really that's doing a disservice to all of us if we try to.
Compartmentalize. Mm-hmm. Instead, I feel like bringing your whole self to business, approaching it holistically and saying, I've been through something which actually speaks to the values and what's important to us today, and say, I know that. This is something that I struggle with. And so this may be a reoccurring thought that I have, and it's all about bringing awareness to that.
Mm-hmm. Taking action that's going to combat that and is going to speak truth to ourselves and also holding ourselves accountable or bringing someone in who we trust to hold us accountable, and that as well there I sometimes we, I think that we see a mindset, like we can even identify when there's a mindset block.
Mm-hmm. But even when we identify it, we're like, okay, but now what? I'm still stuck. Still have the block. What do we do? And I, I wanna tell you right now, the secret to that, the formula is awareness, action, and accountability. Hmm.
Erin Austin: So that you understand like, what is blocking me? The reason I'm not moving forward is my mindset.
So acknowledging what was, repeat the three things again.
Jillian Dolberry: Yeah. So, and it might be different for everybody. It could be I don't have enough time.
Erin Austin: Mm-hmm.
Jillian Dolberry: That's a mindset problem because yes, we all, we all have finite time, but is it really even about time? Mm-hmm. Is the question. Yeah. But it could be about time, money, resources.
Skillset. Mm-hmm. Whatever we feel like it is. Mm-hmm. Narrow down to what that mindset issue is. And in that mindset issue, you're probably gonna tell yourself, okay, but now what? Mm-hmm. What, what is the next step for me here? And so the next step for you is becoming aware of the mindset block, becoming aware of the incorrect mindset that you have, the, the doubt, the unbelief.
And then you want to take action that's gonna combat that. You wanna take action, that's gonna get you moving in the right direction. Mm-hmm. And then you need accountability to keep up with that so that you don't spiral back into that, that
Erin Austin: process. Mm-hmm. Mm-hmm. I like that. Makes alliteration there. Yes.
Jillian Dolberry: Oh yes. I love them. Anytime I can pull that out, I'm all for it. I do.
Leading with Values & Leveraging Technology
Erin Austin: So how do you work with your clients? I know you do have a product that's available, but I'm sure that's, uh, how do you. Drive change with your clients.
Jillian Dolberry: Yeah. I love that question. Drive change. Mm-hmm. Um, so right now we are working with people in a 90 day capacity.
We're currently working on some different offers that could be good for people who aren't quite ready to make that commitment, but I. The core offer that we have that drives the most impact is this 90 day intensive, where we take a deep dive into your values, how you're leading your business as the owner, and maybe even as the operator as well if you're doing all the things.
Mm-hmm. Um, we look into your team. If you don't have a team, we evaluate who you need. We figure all that stuff out. If you do have a team, we figure out. Like, are the right people in your team and are they on the right seat? In the right seat on the bus? Mm-hmm. Um, and then we look at all of your systems and we create machines basically that are going to do all the work for us so that we can actually focus in on the most important work that we do.
Erin Austin: Awesome. What are your thoughts about ai? I'm sneaking that in there.
Jillian Dolberry: Oh yeah. Oh, let's, let's go. I love AI and I.
But I, I love it when it, when I, I have it, I put it in a box because there will always be limitations to what it can do. Mm-hmm. It's never going to replace what we bring to our business in its entirety. And so when you're able to. Identify what it can actually help you with and manage your expectations for that.
And you accept that, I think that you are able to really maximize how it's used in your business. Um, I think where people get in trouble is they're either on one side of the spectrum. They're either afraid of it and not engaging with it at all, or they're leaning on it too heavily and they are. It's kind of putting them in a situation where.
Their business is being presented in an inauthentic way because they're leaning on it too heavily. Yes. Mm-hmm. So I think there's a balance there, but mm-hmm. I, I do really love it when it is sitting in the box that I know it sits in, in my business. And so, yeah, I, I definitely feel like I, but we all. As new things come out and new tools and developments come out with it, we're all like, okay, this new thing is happening.
Are we gonna be afraid of it? Are we too much And you all, we all just kinda have to find our own way with it.
Erin Austin: Yeah. Yeah. I agree with you. I agree with you. It is technology. It is a tool and we control how we use it when, mm-hmm. How, who with? And that's why we need to be aware of the differences. They aren't all created equal and absolutely, you know, people who lean too much into it.
Um, not only is it inauthentic, but to the extent they have expertise, they can dilute their expertise if they're losing their voice, if. You know, by, by leaning into it too much that they're not doing the hard work of continuing to, um, you know, dig into their own expertise. And, uh, and so, but it, it is, you know, I.
But you're missing out if you are completely avoiding it. Although it's pretty hard to avoid it right now, you know? Very true. It's being introduced. It's everywhere. We turn it, it's everywhere. You know, I, I notice I have click of business. I actually don't know how to use it. I never use it. The. My OVM knows how, I don't know, and, but I get the email updates like, oh, we have ai.
I'm like, what? I know, I, you know, okay. But it's in, you know, things, something I do use every day, which is Adobe, you know, they have it. They have, you know, and so it's, they're probably, if you're using any type of SaaS. It's there and mm-hmm. It really is. Whether it makes sense for your business or the particular use case, so,
Jillian Dolberry: alright.
I think too, knowing what's most important to you and what you bring to the table in terms of business really helps you decide how to use it. So if anybody's like, like all of like they're having decision fatigue or overwhelm, that there's all these different opportunities, I just feel like. Let's go back to what's most important and then go from there.
Erin Austin: Mm-hmm. Yeah, absolutely. Yeah. I am on an email newsletter that comes out daily that has updates on, you know, new releases of kind of the usual suspects, new suspects, and, you know, new positions, new, um, legal developments, new like, it's just like, and it is. You know, I'm like, wow. And it's accelerating, obviously, so yeah.
But yeah, but don't get overwhelmed. Just figure out what you need. Like, you know, honestly, starting with some, you know, like your task manager, like what, you know, that is one of the benefits too. Like you can't really delegate if you don't know what the process is. So many of. Just get it done, just get it, just suck it done.
But when you have to break it down into discrete tasks, like which ones can be delegated to human or delegated to AI or some other tool, so another benefit. That's why we really need to understand what's happening in our business. So, absolutely. So, uh, thank you for, for coming. So tell us what's new and exciting in your business?
Anything happening that you wanna share?
Unlock Your Business Strengths
Jillian Dolberry: Yeah. So, um, right now I am pouring a lot of time into creating a new quiz for people to take. That is going to reveal, and by the time this goes live, it might be ready. Fingers crossed. Mm-hmm. So you can find it@jillianberry.com slash quiz. And basically what it's gonna provide you is it's gonna show you how.
What gifts you bring to the ownership and the leadership side of your business. How to leverage those where your watch areas are, and a personalized strategy of how to continue to grow and move forward. And I think it's gonna be really valuable for people. And then after you take the quiz, you get a free strategy call with me and I, I so hope that.
Anyone who listens to this takes the quiz and takes advantage of that because those calls are so life-giving for myself, but also for the people on them. We just get on a call for an hour and we talk about their top three pain points, where they originate from what the core issue is. 'cause oftentimes, we.
We'll list off the pain points, but we're not always clear on why they're painful. And so we really dig into the depth of those and then talk about solutions about how we move forward. So we really go through that awareness, action, accountability, and figure out how they need to move forward and just pack as much value into the hour as possible.
Erin Austin: That is very generous. An our, that's amazing. So I, yeah, I absolutely hope everyone does take advantage of that, although that'll be a lot of your time. But you offered it so
Jillian Dolberry: I did. I, it's my fault. It's my fault. Fill up my calendar, everybody.
Erin Austin: That is wonderful. Thank you so much, Jillian, for joining me today.
It's been a great conversation and, uh, some great resources. We'll make sure that your website is on the, um, in the show notes and where else Jillian uh, Dolan. Jillian berry.com and then where else can people find you?
Jillian Dolberry: Um, I'm most active on Instagram, so my handle is Jillian Berry and I'm very responsive in the dms.
If you ever have any questions about anything we talked about or anything, team, systems, leadership, business ownership, whatever you feel like you have a question on, you feel, if you feel like I can help or need somebody to listen, I'm, I'm your girl, so you can find me over there. Awesome. Well, thank you so much, Jillian.
Thank you for having me. It was a joy to have this conversation with you, Erin. Thanks.