The $1.4M Business His Dad Won't Let Go Of | Confession Booth
In this episode of Confession Booth, host Mike Andes fields two callers seeking advice on scaling small‑to‑mid‑size service businesses. The first caller, a son who has been the operations manager of his father’s 22‑year‑old landscaping and hard‑scaping company (about $1.4 M in annual revenue), explains that despite holding the title he has no real authority: employees still go to his father for decisions, the father continues to handle pricing, estimates, and day‑to‑day crew management, and the son feels stuck. Mike diagnoses a lack of role clarity, emphasizing that at the $1.4 M level the business is effectively a three‑person operation—sales, operations, and admin—each needing a clearly assigned owner. He advises the son to map every daily task, bucket them into the three functions, and formally assign responsibility, starting with a candid conversation with his father. Mike also stresses the importance of delegating low‑leverage tasks and adopting standardized software (e.g., HomeWorks CRM) to codify processes, reduce reliance on memory, and enable the father to step back. The second caller, Miguel, runs a 24‑year‑old printing company with a small staff. He wonders whether to hire an assistant to free him for more sales or to bring on a manager/assistant manager to run shop operations. Mike applies the same framework: rank current activities by leverage, prioritize delegating admin and operations first, then consider an assistant for sales. He suggests identifying low‑value tasks (mail, coffee runs, office upkeep) that can be handed off cheaply, then moving to an operations manager if needed, noting that admin hires are usually easier and cheaper than sales‑focused hires. Throughout, Mike reinforces the three‑function model and the need for clear ownership and systems to scale. Key takeaways: (1) role clarity is essential for growth; (2) map tasks to sales, operations, admin and assign owners; (3) delegate low‑leverage work first; (4) adopt software to standardize processes; (5) use a structured decision‑making framework when hiring.
Chapters
I have the title, but I don't actually have the responsibilities.
At 1.4, this will keep you at this size forever because he's still the hub that everything is tied to.
My father, he just went behind our back, my back, and apologized to all the clients that I tried raising the prices on.
Getting more sales is probably the highest leverage thing in the business for you right now. Anything besides that would be a target for delegation. Welcome to the show. Thank you for coming on.
Hey Mike, thanks for having me on.
Yeah, what's up?
Yeah, so I'm having a little bit of a problem, um, with my business, my family's business. My father, he started a landscaping and hardscaping company about, about 22 years ago. I grew up around the business, and about 5 years ago I joined on as an operations manager to kind of take over the operations role from my father as he was, he was he's kind of transitioning into retirement. And, you know, our initial plan was 5 years ago was to have him kind of step back from the operations role and have me step in. But it's just been a little bit hard as I feel like I've had the title of operations manager, but he hasn't given me any of the responsibilities yet. You know, when people, when our employees come to, when they have any questions, they always go to my father instead of coming to me. I feel like I just have the title but not actually any of the responsibility. So I was trying to get your advice into, you know, what I can do to kind of step more into the operations role itself in terms of responsibilities and not just have the title there.
Okay, so just so I'm on the same page, when you started with your dad, how long have you been in the business, like working in the company?
Yeah, so full-time I've been working in the company about 5 years. Okay. Obviously, I grew up around the company, but full-time it's been about 5 years here.
Okay. And did you immediately start with the title of operations manager? You start out in the field with the crew?
Started out in the field and then, and then kind of worked my way up after about 2 years there into the operations manager title.
Okay. And, and why does your dad think he needs an operations manager? Like, he's ran it for 22 years the way it is. Has it grown a bunch? Or is it just like he wants out of the business? Does he want to hand this off to you one day? Like, Why is he even bringing you up in this role?
Yeah. So, so the original plan was to bring me up in this role so that way my father would eventually step out of the company. Um, but he just has been having a really hard time letting go of, uh, the operations side of the ball and stepping— he's actually looking to retire, um, and just be an owner of the business and not actually be involved in the day-to-day, but he's just, he's been doing it so long, it's been hard on him to actually take that step. Step back.
Okay, and when you say like, is he— are you guys stepping on each other's toes a lot? Is he coming in and like, when you say something, is he going and telling the crew something else? Or is he like checked out of the business? Like, what's his involvement in the day-to-day?
Yeah, he's still very, very involved in the day-to-day. Um, he does go, uh, kind of behind our back and like talk to the crew. Um, like if I— if I'll say something, you know, he'll kind of say something else, not necessarily always intentionally. Sometimes he doesn't realize that I've kind of told the crew something, but, um, yeah, he, he oftentimes, uh, he's very involved in the day-to-day still, even though he, he said to me 5 years ago that he's trying to step out, um, and have me step in, but it just hasn't been happening.
Okay, so first off, do you have any equity in the business, or is this 100% him and he's just like, hey, down the road I will hand it off to you?
Yeah, no, no equity currently. It's, it's him, and then down the road he wants to hand it off. That's the ultimate goal that we're trying to work towards.
Okay, so you're working towards, but do you guys have any like actual plans for this? Like, do you have a timeline? Is it like 2030? Or is this just like, hey, down the road at some point you'll get the business?
We were hoping that would be by now, that I would have fully stepped into the operations role and been able to lead the teams and the crews. But that hasn't happened. All the crews too, when they have any sort of questions, if there's any question that comes up on a job site, they always just go straight to him instead of going to me, and that's been kind of a key issue. I just feel like I have the title, but I don't actually have the responsibilities and the values of being a leader yet in the company.
Right. Okay. And what was the revenue? I missed that part. How much revenue are you guys doing a year?
Oh yeah, we do about $1.4 million. Last year we did about $1.4 million per year.
I feel like your dad, if you guys had talked about and you guys had agreed that, hey, we want to by this time, 2026-ish, have you taking the business over, I'm going to go out on a limb and say he's also frustrated. That it's not happening, and he might not be voicing that. He might actually be somewhat thinking the exact— like, he could very well be on the next line of this being like, I can't get this handed off to my kid. And so I would highly recommend having more role clarity. Right now he is kind of jumping in, as he probably has for the past 22 years, between sales, operations, and admin, but he's asking you to do operations and If you're the operations manager and yet when your crew has a question or wants something, they come to you, you say something, and then they just go to someone else, like, that's, there's no role clarity. And at 1.4, this will keep you at this size forever because he's still the hub that everything is tied to. The crew, decisions from you, I'm guessing he doesn't let you make decisions autonomously. And so I would highly recommend sitting down with him I'm like, hey dad, there are 3 departments in every business. Sales, get the work. Operations, do the work. Admin, get paid for the work. We've gotta figure out all the things that you do and I do every single day and put them into these buckets. And if it's gonna be a split 50/50, we've gotta determine who's taking over and is their name is next to that role in the business. And so, for example, for me, when it comes to operations, my first question is, when someone wants to call out or calls in sick, for example, who do they contact? And that is the operations person. The person that gets contacted when the crew's not showing up. And at 1.4, that's not multiple people, that's likely supposed to be you in terms of getting the work done. 'Cause it affects you. It doesn't affect getting more work, it doesn't affect getting paid for the work, it affects you getting the work done with your crew. And so I would take everything you do in a day, everything he does in a day, and then just put it up on a wall and be like, Okay, sticky notes for every single one. We're gonna organize it into sales, operations, admin, and we've gotta determine who's doing what. Like right now, do you do estimates at all? Are you just out in the field with the crew getting the jobs done?
I'm just with the crew. I've done a couple estimates. I've also tried to raise prices for a couple of our customers, but my father, he just went behind my back and apologized to all the clients that I tried raising the prices on. We've been kind of butting heads in terms of the actual operations a little bit, Essentially, you know, he's very old school in the way that he runs the company, and I'm trying to modernize it a little bit. But yeah, I'm still doing, doing some estimates as well there.
Okay. Yeah, so like I would have this conversation with him. Even the fact that like raising prices is a two-person decision in this company at this size isn't necessary. Getting paid for the work is an admin's role. So whether you have an office manager or you have That has nothing to do with operations. And so I would focus on getting role clarity between these 3 departments. Now, when you have a $5, $10, $20 million business, this starts to get sectioned off. And outbound sales, inbound sales, operations starts looking very different based upon certain, certain types of services. Admin starts having different sectors of accounts payable, payroll, etc. At your size, it's likely that this is a 1-person job for sales, a 1-person job for operations, and and a one-person job for admin. And we gotta get clear in terms of all functions of the business and then assign that function to a role. And right now, when I hear there are price increases that we are having disagreements over, I hear probably your dad that usually does estimates over here. I see the operations manager over here. And of course we're gonna have disagreement 'cause no one's clear on who's responsible to get paid. And so, I would have this conversation, I'd get role clarity. I remember doing this and I was stepping all over the toes of my office manager at the time, which was Liz, and we had a 3-hour conversation and we wrote down the 40, 30 or 40 things that I did every single day and we just started delegating it. Like everything from opening up the gate in the morning to opening up the shop, like unlocking it, uh, to at the end of the day, like who would close up the cash register. Every single thing I did, we just listed it off and then just started delegating it. And it had to fall into these buckets of sales, operations, and admin, because I just— otherwise, I was in the email, she was in the email. She was answering the voicemail, I was answering the voicemail. Then customers get contacted twice. Then I get frustrated because I'm out doing estimates and I'm also in the email inbox responding to people. You have to have role clarity, otherwise will inevitably create friction inside the relationship, whether it's father-son, whether it's spouses, whether it's just coworkers and employees, if you don't have role clarity, especially at $1.4 million, it will not grow, and furthermore, you will constantly be colliding into each other throughout all functions of the business. What type of customers you get is one person's responsibility. I don't need to be balancing, it slows the whole organization down when I can't just make decisions as a salesperson. Operations, I shouldn't be bringing 3 people in about the fact that someone is late to work. Or is gonna get a performance improvement plan, or that a customer's job went south. A customer's job going south is the last thing you want your salesperson to hear. Your admin doesn't need to deal with it. That's an operations manager's job. And so having role clarity, and it's likely that underneath each of these there are 10 to 20 different tasks that just need to have clarity of who's responsible for what, and then putting the name of the person that is responsible for these 3 functions. Now if you're a smaller business and not doing $1.4 million, Whoever that was calling, if someone else is listening, and you're doing 300,000, 400,000, you're not gonna have one person for each of these. But as you grow the business, especially past a million, we have to have role clarity. Otherwise, it's just constant war with each other. 'Cause we're stepping on each other's toes all the time. Your office and admin person is trying to be in the email and answer voicemail, but you're bouncing in there on the weekend messing them up. And you're supposed to be focused on getting more jobs. You're supposed to be focusing on training the crew. And so, if you're smaller than $1.4, I'm gonna first delegate this task, admin, then I'm gonna delegate operations, and then as I pass that $1.4, $1.5 million, then I focus just on sales. But just make sure that when you delegate it, you really actually let it go. You're not bopping in on the email on the weekend. You're not checking the voicemail. When you hand off operations, you don't do what the father of whoever just did this, like, "Oh, I want you to be my operations manager." See how discouraged his son is? If you, again, I'm just trying to make this relevant to everyone else listening. If you have an operations person or a general manager and they're responsible for the crew, don't go around their back. If an employee comes to you after you know they just got an answer from the GM or from the operations manager, you back up your operations manager and tell them to go back to the operations manager. And you say, hey, did you already run this by so-and-so, the operations manager? Oh yeah, okay, whatever they say, I'm going with it. And you say, well, what if I wanna add to it? What if I actually disagree? It doesn't matter, 'cause as soon as you inject and you jump out of your role at this size of business and you jump into operations, you have handicapped forever your operations person. And that is far more detrimental, handicapping another role inside the organization, far more detrimental to the business and the growth of the business and the culture of the business compared to like one job, one customer, one instance going wrong. You can always go behind a closed door and talk to your operations manager, but don't have the people that are reporting to them come around them to you, and then you give a different answer. Very detrimental to the culture of the business.
Hey guys, I want to show you a little bit behind the scenes, a little bit how the sausage is made. This is the media team, and this is where we do the, uh, videos. Out here is where we did the recording. We have some offices over there. That's my office. But then over here is the media team. So it's early morning, so they haven't come in yet. This is the HSM crew. Some offices here, but like a couple of the team, we have a few in like Tennessee, and Minnesota and Texas as well. But this is my office in here. But I wanted to really quickly just jump in here at this part of the video and say this is why it's so important to have software. And I understand with the advent of AI, it's almost on trend, like, push against technology. But if you look historically, that like never works out. The companies that adopt the technology are the ones that scale the fastest. And so I highly recommend using software. Now I'm biased because we have HomeWorks, but I don't care if you use HomeWorks. Use a CRM so you can hand off operations. And in this case, what we're talking about right now, this example, the ability for the owner to be able to hand off operations will come down to having systems. And systems is standardized and simplified. Standardized and simplified means I do it the same way every single time and it's easy to do. And using software is the best way to do that. And so if you talk to any big business owner, they use software. And the reason is because as you begin to scale and get bigger, it's harder and harder to keep everything in your head. And so if you've taken pride in being able to do everything in your own head instead of using software, I highly recommend using software so that If you were like me back when I was 21, got stuck underneath the dump truck, if you get taken out, there's videos, there's systems, there's procedures, there's a way to do a dispatch board. All of that's automated inside the software.
And so go check out HomeWorks.
The first 50 customers are free for people that are just getting started, or for those that might want to dip their toe in and see what's it like to have systems when it comes to software.
So go check it out.
I highly recommend it. I do not care if you use HomeWorks, just use systems so you can scale your business.
Mike Andes, actually. Miguel, how are you?
Good. You don't have to say your name, but there it is. Miguel, welcome to the show.
I know it's all good. This is a healthy question for the most part, I would say. So I'm at the point— we've been in business almost 24 years. We're a printing company. And right now I'm at the point we have 4 people in customer service. One of them is part-time. And then we got our graphic designer and our production person. So what I'm debating right now is I'm the best one obviously at sales because I'm the business owner and, and, and, uh, we working on the better process, sales process for our employees. So what I'm debating on is should I hire a, an assistant so I can do more sales so I don't do a lot of the small tasks, or should I look for a manager or an assistant manager with the potential of being helping me run the shop.
Totally. Like, no matter what you do right now in terms of delegation, Miguel, it gives you more time to do higher leverage tasks. And so the best way to delegate, in my opinion, is rank all the things you're currently doing from lowest leverage to highest leverage. Getting more sales is probably the highest leverage thing in the business for you right now. Anything besides that would be a target for delegation. Now I believe there are probably some tasks you do that you could hand off to these admin folks. You just gotta delegate it. You gotta create a system and hand it off. And so I think a lot of times we jump to like, I gotta get an operations manager or I'm gonna get something, some manager, versus just like, oh, there are like 12 tasks I do just because that I could just hand off. Even though it's not home services, it's still the same thing. You got sales, you got operations, and you got admin. And I believe that right now Miguel, at his size and doing very well, probably is doing, I'm just gonna make this up, 60% of his day is probably doing sales. I would go ahead and guess that 30% of his day is doing operations, and I would assume, I'm just gonna guess, 10% of his day is doing admin. And so, yes, he could get an assistant to help him with sales. He could do that. I first, though, want to delegate all the lower leverage tasks in the business, which is admin and operations. If right now he's doing a $100 per hour task in sales, I wanna hand off anything I can go out and delegate by hiring someone for $50 an hour or $30 an hour in admin. Now, everyone also thinks, the other question Miguel had asked is like, hey, can I just go get an operations manager? Yes, that would give you 30% of your day back, but before I do that, I want to make sure I get this. This is the easiest low-hanging fruit in the business, which is the low-leverage task that I'm gonna guess is things like checking the mail, opening up the office, adjusting the thermostat, getting coffee, filling up the fridge, ordering things from Instacart to fill up for the office team. These are little things. I'm not saying Miguel specifically does this, but I believe that many of us could simply ask ourselves, what am I doing? The 40, 50 things I'm doing in a day, and I think some of them are really low-hanging fruit to get delegated. And do this first, 'cause this is likely no extra cost, not a lot of systems building, no time of Miguel to be able to hand this off to his existing team that's doing admin. And then I go after operations. Also usually easier to find an admin person compared to operations. Also, usually easier to find an operations person, especially if you're doing work like operations out in the field, like the printing. Usually easier to find that person than a rainmaker, like Miguel is, in sales. It's easier and cheaper. And so this is the way I want you to delegate all aspects of the business. Admin, operations, and then sales.
