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2026

How to Get Out of the Weeds as a CEO (And Actually Stay Out)

Baker_Dec15_021.jpg

Sabrina Baker 

Mar 31, 2026

15 mins 16 secs

If you have heard the advice to "get above the business" and walked away with no idea what that actually requires, this episode is for you.

Most founders are not above the business at 15 employees. Many are not above it at 50. And the longer you stay in the weeds, the more expensive that pattern becomes — not just for your calendar, but for your growth ceiling.

In the first episode of the Fix Series, Sabrina breaks down why getting above the business is not a mindset shift or an emotional letting-go. It is a build problem. And like any build problem, it has a process.

That process starts with having the right people in place to receive delegated work, extends to getting everything that lives in your head out of it and into a system, and depends on a kind of trust that most founders have to learn the hard way. It also does not happen once. It happens with every hire, in a repeating cycle, until most of the day-to-day no longer requires you.

This episode walks through all of it: the three things the transition actually requires, why founders stall in the middle of it, and what your calendar realistically looks like week by week as you move through it.

If you are sitting at 20, 30, or 40 employees and you are still the person people come to when something breaks, this is where the work starts.

  • Back in the "What Breaks" series, I said that at 15 employees, the CEO needs to be above the business. They need to get above their business. That was the first thing on the list. Not HR infrastructure, not roles, not hiring standards. The CEO getting out of the day-to-day was first, because nothing else on that list or any other list works if you are still in the weeds. But here's what I didn't say, and what I see constantly with our clients: most founders are not above the weeds at 15. They're not above the business. They're not above it at 25. I have worked with founders at 50, 60, and even 75 employees who are still functioning as an individual contributor with a CEO title. And the business? And their sanity? They're paying for it. This episode is the first in the fix series: we are done diagnosing, now we build. And we're starting here with getting above the business, getting out of the weeds. Because if you can't do this, none of the other fixes are going to stick. Today I'm going to tell you exactly what this transition actually requires, why most founders stall in the middle of it, and what the week-by-week reality of doing it actually looks like. If you're not already subscribed and you are leading a small employer with between 1 to 100 employees—I say 1 to 500, but this is really for 1 to 100—hit that button now. This fix series is going to go deep on every breaking point I named in the previous series: onboarding, leadership, compensation, systems, all of it. This is me as a founder speaking to you as a founder, through the lens of building my own business, but maybe more importantly, doing the work I do has allowed me to work alongside clients as their business has grown. So this insight is cumulative from hundreds of small businesses over the last 15 years. My style is to be rather direct, so let me do that now: getting above the business is not a mindset shift. It is not about learning to let go emotionally or trusting your team more—although that's important, we're going to talk about that—it's not about thinking more strategically. Those things matter, and you do have to do them all, but they're outcomes, not inputs. You don't think your way into this. You build your way into it. So this is going to be pretty captain obvious here, but I'm going to say it anyway: you cannot delegate work that has no one to receive it. Getting above the business starts with having people in place who can take on the work you're currently doing that you shouldn't be. Not just the roles that feel urgent for revenue, but actually take work off of you. And while that felt obvious, what I see is founders sometimes trying to delegate work to people who are not equipped to do it. Yes, in small businesses, you have to wear many hats. But having your finance person also building your website might be a bad idea. So this is really about looking at who you have, but also who you should hire. Most founders hire reactively. Someone's overwhelmed, so you post a job. The question before you post anything is: what work do I need to stop doing, and who needs to exist for me to stop doing it? That is a different hiring question than most founders are asking. Now, do not get me wrong, your first few hires may very well be people doing things you can't, like marketing and sales. Those are really important. I totally get that. But it's why this fix of getting above the business was mentioned in the 15 employees video. By that time, you should have hired those essential staff members who supplemented what your skill set was. They are doing the things that you couldn't do. And now, by 15, you're scaling, which means you have to hire strategically and think about how every hire supports growth. And that growth means taking things off your plate that you shouldn't be doing so you can work at 30,000 feet rather than 10,000 feet. The second thing this requires is getting what lives in your head out of it and into a system. Now listen, I mentioned this in several of those videos because it is the thing I see that never gets done until it becomes way too painful not to do it. As a founder, you carry an enormous amount of knowledge no one else has access to. It's all in your head: how decisions get made, how clients are handled, what good work actually looks like, what's acceptable and what isn't. As long as it lives only in you, every person you hire will eventually need to come back to you to access it, or they're going to make up their own way of doing it that isn't what you ultimately want. Inside of Acacia, we have a program called SEED, which is Skill Enhancement and Employee Development. It is our SEED program. Acacia is a tree. I try to keep with that theme as much as I can. SEED, our SEED program, is how every new employee learns the Acacia way, not just the client work, but how we communicate internally, how we handle our group chat, how we work remotely, how we give feedback, how we escalate things when we need to. All of it is documented and taught. These are all things I was doing when I was by when I was by myself. But now they're documented and taught, not because we're a large company. We're really small. But because I made a decision early that I, the founder, cannot be the answer to every operational question. I needed them to learn it on their own. If you are still the person people go to when they don't know how to do something, then this is the stage you are in. You are ready to get above the business, and you need to build processes that run without you while still having the spirit of what you built. The third thing this requires is trust, true trust, that allows employees to do their job using their own judgment within your guideline, but on their own. Real delegation means realizing your people will not do the things the same way you would. That's what's really hard for me to learn. Their email is going to sound different. Their client call is going to go differently. Their process will have steps you wouldn't have included. And as long as they're hitting the result, as long as they're operating within your behavioral and performance expectations, and as long as they're operating in your documented standards, that's okay. It has to be okay. Because if you are correcting the way things are done, rather than whether the outcome was achieved, you have not actually delegated anything. You've just created a slower version of yourself doing that same work. Micromanagement and being above the business cannot coexist. You have to choose one. Let me tell you something about this you may not be thinking about on the surface: getting above the business is not a transition you make one time. It's not an overnight thing. You hire someone, hand off the work, and you're done. That is not how this works at all. Getting above the business, especially if you're around that 15 mark and so you're scaling, it is a wash, rinse, repeat cycle. You hire someone, identify what work you can now delegate, document it so they don't constantly need you, you trust them to do it, and then you pull yourself out of those tasks. And now you're going to repeat that with the next hire. With every single hire, you extract yourself from another slice of the day-to-day, not all at once, iteratively. By the time you have five or six people who have been through this process, you are effectively and genuinely above the business. Because now most of that work has been delegated, it has been documented, and it's proven to run without you. But now there is a flip side to this: when you are really small in that under 15 stage, you may have to step back into the business from time to time. If that person you delegated work to leaves, you may have to step in. It is what it is at that size, but at least you only have to do it until the person is replaced because you have already done the documentation part, you know how to delegate, so the replacement hire delegation process goes way faster. So let's think about how this could look on a calendar. Like, how long does this take? At each stage of this cycle, how long does this process take? So you hire someone, you've got one to two weeks after their hire, nothing is going to change. Your calendar is still reactive. It's going to be really, really full because you're training this person, and that takes a lot of time. You are answering their questions. You're showing them how things work. This is very normal, but it's also very temporary if you're building the documentation system alongside it. If you're not writing things down while you're teaching them—and that's not just them taking notes, that's you really documenting it—you're going to be having the same conversation with the next person you hire. The first two weeks is all about just getting it out of your head and into their documented knowledge. Weeks three and four, they're starting to take on the work, maybe, but they're coming back to you with a lot of questions that you've probably answered before. And every question they ask that should be written down somewhere is a documentation gap. You want to fill it in in real time. And if it is already documented, you want to point them to the documentation. Don't answer it verbally and move on. Make them use the documentation. After that, weeks five, six, the work is running. You're still checking in, but you're not really in the work as much. You've noticed things that you would do differently, and your trust is tested. The question is not, "Is this exactly how I would do it?" The question is, "Is the outcome right? Is it within the standards that we've defined?" If yes, let it go. If not, address it. Becoming a high feedback culture, not because you are trying to find people doing things wrong, but because you want to help them get it right, is how you get above the business. Doing this early and often builds employees who can take feedback without everything feeling like an attack. Now look, some roles take way longer than this. But ultimately, if you're doing this right, you should be able to move through this in about seven, eight weeks. And by that time, the slice of the business no longer requires you. Your calendar reflects that. The time consumed by this work is now available for something else: strategic decisions, client relationships, the next hire, the next function you need to extract yourself out of. And then you do it all over again. The cost of staying in the weeds is not just that you're busy. The cost is that the business cannot grow past the capacity of you. At 15 employees, you are a bottleneck. At 25, you are a more expensive bottleneck. And at 50, you are an extremely expensive bottleneck surrounded by people who have learned to wait for your permission to do anything. That learned helplessness, that organizational habit of routing everything back to the founder, is one of the hardest things to undo as you grow. And it compounds with every hire who joins while you're still in that pattern. This is why it's important to do this at 15 employees. The founders who navigate the later stages well, 75, 100 employees, did not get there by making one dramatic shift. They got there by running this cycle repeatedly. The next video in this series goes into HR infrastructure, the non-negotiable baseline that has to exist before any of the future fixes hold. I know you want to cringe at the idea of HR, but the earlier you start putting as much effort into the structure inside your business as you do on the product or service, then the faster that you are going to grow. I understand that you don't believe me when I say that that work, that internal people structure, is growth, but I'm ready to prove it to you in our following episodes. If you're sitting at 20, 30, 40 employees, and you recognize yourself in this, you're still answering questions you've answered before, you're still in the client work, you're still the one people come to when something breaks, this is where the work starts. This is how you start to get above it. I would love for you to connect with me on LinkedIn. My LinkedIn profile will be in the show notes. You can send a connection request and maybe tell me how many employees you are sitting at right now. I would absolutely love to connect with you. Most founders build reactively. They focus on sales, marketing, and product, and they treat people as an afterthought until the people start costing them everything. A business where people building is intentional, where leadership is developed, where HR is treated as a growth strategy, not a compliance function, that is a business that scales. Let's build that.

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