The Business Millennials Podcast

2.14 - The $500K CEO Crisis: From Operator to Strategic Leader

• Ashley Dreager • Season 2 • Episode 14

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In this episode of the Business Millennials Podcast, Ashley and Safa explore the critical challenges entrepreneurs face when transitioning from operator to strategic leader. They explore the hidden traps of burnout, the importance of delegating strategic roles, and how to create sustainable business growth by stepping out of day-to-day operations. 

Key Takeaways: 

  • Recognize the signs of being trapped in operational roles, even after reaching multi-six or seven-figure revenue
  • Understand that strategic growth requires creating time and space by investing in management roles
  • Learn how to audit your current business state, including time allocation and team structure
  • Identify the shift from doing money-making activities to planning future money-making activities
  • Develop an objective approach to team performance through clear metrics and key performance indicators (KPIs)

Timestamps:

  • 0:58 - Overview of entrepreneurs reaching multi-six-figure revenues
  • 2:43 - Common traps entrepreneurs fall into
  • 5:48 - The importance of creating time for strategic work
  • 14:27 - Steps to transition from operator to strategic leader
  • 22:14 - Tactical steps for business transformation

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Intro:

Welcome to the business millennials podcast. This show brings you strategic insights through raw and unfiltered real world advice to accelerate your business growth for longterm success. I'm Safa Harris, and I'm Ashley Drager. We're the founders of scale and thrive co a full service marketing and business development firm, helping visionary companies scale sustainably. Expect us to have the uncomfortable conversations that no one else is having. We'll break down what it really takes to grow and scale your business beyond six Seven or even eight figures, as well as inspiring interviews with diverse leaders across marketing product development, sales, and more via fly on the wall as we conduct strategy sessions with business owners, experiencing issues such as plateaued income burnout and generally dropping the ball, giving you the tools and resources to break through your own roadblocks, but also personal development methods to grow you as a balanced conscious leader, amidst business growth. Let's jump into this week's episode.

Ashley:

Okay, so we see a lot of clients that get to multi six figures a year, around 500k, mostly on their own. They may have a couple of team members supporting them, you know, social media, content repurposing, maybe a VA, that kind of thing. But they're very much able to get to that point without bringing on the higher level strategic roles to take things off of their plate. So that they can then lean into that CEO role, the vision, the visionary for the business, the leader for the business, because they're still wearing all of those hats on their own. But we have also seen from clients in the past when they don't take off some of those hats and hand them off to dedicated management. Members for their dedicated, they don't, they don't expand their management team.

Safa:

Mm hmm.

Ashley:

They keep all of those hats. There's going to be a downfall. It's going to cause burnout. It's going to cause a lack of quality in their delivery and their operations are going to have leaky buckets. There is a wide range of things that is going to Be the result of them not delegating or not outsourcing some of those strategic roles or bringing in the support for those strategic roles. So I think that it would be really beneficial to talk about. what some of those, um, traps may be that people fall into because nobody intends to get burnt out.

Safa:

Yeah.

Ashley:

intends to run themselves into the ground or build a business that's completely unsustainable to where they're like, burn it all down, get rid of it. I hate it. I'm going to go back to corporate. Nobody intends to do that. Right?

Safa:

Yeah.

Ashley:

so what are some of those indicators that if they haven't started handing off? those responsibilities yet, that this is a good time to do it. Because, I mean, we've, even though we started this out saying, you know, a lot of people get to multi six figures, we've had clients that are in multi seven figures that still haven't done this yet. So just because you have moved past that point doesn't mean that you are immune to these traps. Yeah. Mm

Safa:

Honestly, it really depends on what you're trying to make happen in your business. You can be a solo business and be at 500 K and if you're cool with the life and you're cool with everything and you just want to keep doing what you're doing day to day, and keep on going, these things and these signs are in what we are considering a trap is not good. That's not good. It's not a trap to you. It's not, these aren't problematic, but if you are looking to scale past and you don't want to be in the day to day, if you want to be doing more with your business or with your life, and you want to be having more space and capacity and, or pushing more or working in different areas or making different things happen in your business, like, This is the trap. This is the where, which, what can I get you stuck? So I know for us, we often say, like, The two main areas for business for success, sustainability and making things happen is going to be like time and money, right? in this scenario, if you want to be doing things in your business, If you want to be making growth happen, if you want to doing all of that, you need to be creating time. For yourself to be able to do growth focus activities and transitioning yourself into a new position to be able to focus work effort time for yourself there so you're going to need to create time. And how are you going to create time? You're going to put money into it. You're going to put money in by, Investing in strategic and management roles that even if you have implement your team members, you are spending time in that management role, managing them. So it's like the next point of like, okay, well, I need to stop managing them I need to bring in this leadership team so I can really step out and

Ashley:

hmm. Mm

Safa:

visionary, strategic role. And that's where I'm putting. efforts and my time and my energy is going and how do you know that, like, you're not doing that? Even if you hired a management team member, how do you know? That you're not stepping into that role, may have created the time, but you kind of let it slide back and go away. You may have invested the money to create that time, you're really going to know, but if you're still in the day to day, if you still know. What's happening in your business on a day to day on like the perfunctory, like, this is what makes it run. And like, what's going on and like status of things really having to get like a debrief or anything like that, like you're too in the weeds. You like, you really, honestly, if you have the proper systems and processes and you know, your stuff works, there is absolutely no reason for you to not trust the people you've put in place to get it done.

Ashley:

hmm.

Safa:

If that done right, and if you feel like you can't trust them diagnosis, that's where you need to look so you can get out of the

Ashley:

Mm hmm.

Safa:

out what you need to do, but there should be no reason why you need to know the status of every task everything

Ashley:

Mm hmm.

Safa:

If your systems in place, they're going to work and it's going to happen you don't need to be in the weeds and you're either in it because. can't trust them, you have an internal block, your systems and processes aren't in place, so you need to be solving those problems. there shouldn't be a reason for that. and then, so that's going to leave you no time to be strategically planning, because you're going to be so far in the weeds, you can't look in the future if you're stuck in the present.

Ashley:

Mm hmm.

Safa:

In all of that same line is if you are a big part of that system, and the team keeps coming to you, be like, oh, what's the next step? Or what's this? Where's that? What's that? You have a system problem? Like, those are the, the you are in the day to day. And the reason you don't have time for strategic planning is because the team is coming to you. You don't have the system processes. You have an internal block or you have a lack of trust. But like, what is that lack of trust? Where is that coming from? That's all going to even if you've invested in management and strategy and anything like that, if you are in the weeds, you're going to keep yourself accountable. From doing all that and then it's going to put you in this position where you're out of time, out of cash, and you're going to put yourself and you're going to box yourself into a corner where you're like, okay, well, how do I get out of this either? Because you're so time constraint, you know, you're going to be so cost constraint, like cash constraint, right? And you haven't had time to forward ahead down the road to prevent fires, to put them out before they get too big, or okay, what's the next iteration? What are we doing next? And then you're up against it, and you're being reactive in what you're doing, and that's going to stunt your growth. Uh

Ashley:

Yeah, on the topic of fires, fires will always come. regardless of what size or stage of business, it's how you handle them that is going to change. And when you are stepping out from the operator role and into more of a strategic leader role, you really need to be approaching those fires or those challenges that come up from a strategic proactive perspective. Instead of saying, Oh my gosh, this fire is here. And react to put it out, right? Like there's two different,

Safa:

huh.

Ashley:

And that looks very different depending on being proactive versus reactive. So this may feel like old news, um, by this time, but, uh, for the MEMS was very much in a reactive state. Once they launched their brand, nothing about that was proactive anymore. Once they started getting the feedback or backlash from their community, they went into reactive mode. And a key example of this was that they, they canceled an order out of fear that the customer was going to make a bad review. Of what they purchased and they got called out on it and they said, yeah, we did cancel the order because we got word that they were going to make a bad review and that's not okay. And that is very much a reactive decision that was made. That was not strategic. That was not from a leadership perspective. And I think if they had taken a step back. separated their personal feelings from the business or had that, that management support on their team that could give them that objective perspective. It would have, they could have proactively.

Safa:

enough from the day to day with all of this, like,

Ashley:

Mm hmm.

Safa:

in on them. It would have given them

Ashley:

Yeah.

Safa:

to not be so emotionally involved in the situation. It would give them that separation to have an objective reaction. And I think

Ashley:

Mm hmm. Yeah. Yeah, exactly. Mm

Safa:

that is a big thing where people get stuck as far as, like, internal blocks. like, Oh, I am my business. This is me. I have done everything into everything wrong with it. Is something wrong with me? Everything I'm not a part of that is the smallest amount of not okay, is that I am not okay. Everything that goes

Ashley:

Mm hmm. Mm

Safa:

me. so that leads to like these control issues and then having to be a part of everything and not being able to let go and all of those things, a part of when you do let go and you don't know about. The nitty gritty of the day to day and things are just turning and you're just looking at the numbers and you're just looking at the higher level things and you're making long term strategic decisions is that each of those you start getting and further away from all of those small things that are personal reflection of you as to they're not a personal reflection of you anymore. And especially when you don't know about it and it just kind of Doesn't actually really matter. It loses the power

Ashley:

Mm

Safa:

and your nervous system and how you're making those decisions. So it's easier to let go and actually do that service for your business to grow it

Ashley:

hmm. Which, I know that can be a lot harder for personal brands versus like a brick and mortar brand, for example, but it still has to happen that same way. You still have to remove yourself. And even if you have a brick and mortar business, if you have a product based business that isn't a personal brand, It's still very personal to you, so it is still easy to fall into that trap of a direct refraction on you versus on the business. but, um, so we've talked about what some of the indications are that you're falling into that trap or that you are already in that trap. So if we wanted to, if, if you wanted to shift out of that, there's probably three or four things that. You would want to keep top of mind when you are shifting from the operator to a strategic leader.

Safa:

So one is going to be really making the decision. To want to not be in that position of being an operator of really wanting to give your business space to grow outside the constraints of you as like a human being and as a person and making that intention of like, okay, yeah, no, I really, really want this. So I need to do. My part to make this happen and not let these other things get in the way of like not being able to let go or needing the perfectionism and everything being a reflection of you, whatever, and making that first decision of being like, okay, yeah, like I'm going to work on this. I want to make this happen. Then I'm going to do that. And then it's going to be a matter of like, okay, so how do I make the transition? And just like everything you're going to realize. Okay, where am I working? You're going to do that current state assessment. You're going to do that audit being like, okay, where am I spending my time? What am I working

Ashley:

hmm. Mm

Safa:

What can I? Give away and what is something that's actually strategic and growth oriented that I need to do. I think looking at like pre 500k revenue, the thing used to be like, Oh, you should be working on your money making activities. Now you are moving into, someone else should be doing your money-making activities. Someone else should be managing those moneymaking activities. And you should be in a place of deciding what are the next moneymaking activities that need to happen.

Ashley:

hmm.

Safa:

I think that makes a distinction of like. Oh, we hear this all the time. You need to be working in the moneymaking activities. It's like, you shouldn't be working in the moneymaking activities anymore. You need to be evolving out of those and into the future moneymaking activities. And that's what you need to be looking at with your time allocations of what you, where you need to be. Where you're at, can go away to someone else and where you should be focusing and making the decisions and things like that, that need to happen to get you to the place. So to kind of like

Ashley:

Mm hmm. Mm

Safa:

Audit your time and your energy and what's going on and where things are going, what should be staying on your plate, you should be focusing on, what you should be doing for strategic work, future money making activities, and then how you can build your team and who needs to be in place to make that happen. And then how are you giving them the resources to make that happen? And then you move into like, okay, great. Let's put all that in place. What needs to happen to make that happen? And then looking into, okay, now let me focus on the future of what my plan is to continue to grow this business.

Ashley:

So something that you touched on a few times is the team structure and the organizational structure, um, and how that's going to need to shift and evolve over time. Um, because one of the, that could also be a, a pretty big indication that you're. You're ready to focus on that shift and that transition when people are pushing back a lot, or when you realize that you don't have people in the right seats. Um, maybe that those team members grew with you and their role evolved. Maybe there's a little bit of scope creep going on and now they have all these things on their plate that really isn't it's not their forte. It just kind of happened that way.

Safa:

Mm

Ashley:

you know, when you're auditing your current state, looking at where your team can be optimized to, I think is a, is a really important one. Um, cause I know on the marketing side that that can really, that can happen pretty unintentionally where you have. one person handling all your marketing activities when really you should be having more specialized skill sets within those. Um, because while everybody would love to have that unicorn, uh, ads, copywriting, social media, email, those are all specialties. So just because one person is handling all of those doesn't necessarily mean that that is going to, that's the best bang for your buck.

Safa:

Yeah.

Ashley:

the best, um, outcome.

Safa:

Yeah,

Ashley:

Yeah.

Safa:

role, and you may or may not necessarily think that, well, they're either stepping up and doing what you need to them. To do, or you're getting a lot of pushback from them being like, okay, well, we've decided to do this and now you've changed this or you're not letting me do my job or you're, or like, oh, well, we had this handled and then you came in and did X, Y, Z, and there's like stepping on toes and those kinds of things happening in that tension and that pushback that is an indicator of one, either the team's not the right fit. Or it's the wrong people. That's not really what you mean, or it's a matter of like, they are really ready to take your business to the next level. And it is time that they are ready for you to step up next into that next phase and give them that space. And if you're seeing those things, a big part of you being able to step out is to be able to fill where you have been and really auditing, seeing where your team is, who's doing what, and who should be doing and shouldn't be doing and what they should be in like really defining real roles who's responsible for what and making you're building the roles or the feet of what needs to be done. And what works together and then who are the right people in those seats, not necessarily the right people and then building seats around them. And that's going to give you more confidence to kind of step up and out, but having that team pushback and those kinds of like issues, if you're having those, it's kind of time to make that assessment. And. We kind of do your org chart, yourself of what your seat should be and building a team from there understanding that

Ashley:

Okay, so. Now what? What would be the next step? If they're, you know, if your listeners are like, yep, this, it's time I need to, I need to buckle down. I need to get this moving. I need to get things going. I, even if things are fine, I need to make sure that they're intentionally fine versus things just happened to work out that way. What, um, what would be some very tangible steps for them to take?

Safa:

Yes,

Ashley:

this episode. Uh,

Safa:

doing an audit, figuring out where things stand as far as who is doing what in your business. Like, that's going to be like. The next 30 day, your first set of priorities of who's doing what and what am I doing and what should I be doing and the things that I should not be doing, where does that go? Does that fit in into roles that we have under the roles look good or do the roles need to be reworked for this new structure of almost like hierarchy? Of like, okay, me strategic next management are the brick the pieces that are in people that are making up this team to get things done. Are they right? Are you allocating your resources in the right way? And if not, what should they be looking like and what you should be doing? And then from there kind of doing like, okay, well, how do I make the changes into. What they need to be. And what and things do I need in place for those roles to be successful? What systems that need to happen? What needs to happen so that if new people are taking on new skills and roles that they're supported and understand and the systems are there to make sure things are working in the way they need to be working and going and doing all of those things? And then from there, really making sure that you're continuously looking at this and working through the data and checking in on the people and the work and everything like that at a higher level instead of at the day to day. So some like metrics or things like that to think about that are going to be a lot less. tangible than say, like a marketing metric is going to be, okay, so 30 days from now, how is the team performing? Is everybody doing the things in the role? Have I actually spent more time in the strategic role? have I spent more hours of me working there? Have I seen the actual change from X, Y to Z in that happening? Are team members hitting success metrics of what their roles look like? and that's going to be different for everything they're doing. And is there more space in your role as of itself to do more of those growth things that you need to do in the future money active making activities we were talking about?

Ashley:

if anybody is watching the video of this, the reason why we keep smiling at each other is because you can hear my kids like stomping down the hallway. I'm hopefully going to be able to edit all of that out. But just know that there's extra noises at my house that, uh, that we can hear at the time of recording, um, no, I think that those are, I think that those are really good steps, especially at looking at the KPIs and the metrics. Um, because that, that will really shift you from I've outsourced this, they're managing it to. I'm managing this team member. I'm managing this employee. I'm responsible for the success of this versus Oh, 10 99 contractor. They just need to deliver it. Right. Like there's, there is a mindset shift there. So yeah.

Safa:

know this is tangibly what I need to hit. And especially as you're moving out of like the day to day and watching every little thing if it happened or not, it didn't happen, whatever. You have this clear way to like, have a pulse. To see what's happening. What's going on? Are people hitting what they need to do? Are they a good fit whatever it may be and seeing that and seeing maybe they just lack the ownership and they're not doing it They're not a good fit or there's some other gap or whatever that you can Spend time on to be like, okay. Well, what are we going to do about this? How are we going to fix this? What are we doing? What's the solution instead of being like, well, let me just do it. Let me just do that. Um, type of thing um type

Ashley:

The numbers help you stay objective.

Safa:

Yeah. And

Ashley:

So, yeah, yeah.

Safa:

because it's like a way for you to check in without you having to like check in and like be in there.

Ashley:

Yeah, exactly. So if building this out is on your to do list, if, deep diving into these areas is something that you have been wanting to do, but you're just really not sure where to start. Um, I would encourage you to take advantage of our free audit. So we will break that down step by step, give you those action plans to know what, where to put your attention now versus where to be putting your attention a few months from now, high level projects, so that you can start to see that path forward and get that clarity to start doing it on your own. And of course, if you decide that you don't want to do it on your own, we are more than happy to come in, work alongside you, take that off of your plate. But this free audit really is It should be a paid offer to be honest the amount of information and the detail that you get the clarity that you'll get When we send that email back to you Is so valuable like it really is enough for you to hit the ground running and DIY it if you choose to do so No obligation on the back end to work with us. We just want to see you succeed and we want to We want the ripples to go further and those aren't going to go further if everything stays with you. So, we'll link that in the show notes for you to check out.

Outro:

And that wraps up another episode of the business millennials podcast. We hope you found this conversation, thought provoking, inspirational, and helps you make a larger impact with your business. Growth is not just about profits or revenue. It's a journey of personal development, contribution, and bettering ourselves in society. Our challenge for you take at least one key lesson from our time together today that you can apply not just to your business. But your relationships, creative expression, wellbeing, and personal evolution to, we appreciate you tuning in. If you enjoyed this show, we invite you to pay it forward, share it with an entrepreneur, creative student, or community leader who needs an infusion of insight or inspiration right now. And make sure to subscribe on Apple podcasts, Spotify, or wherever you listen. So you never miss a single episode. And if you like what you heard, leave us a five star review. See you next week.