Overwhelmed? It’s Probably Time to Hire—Here’s How to Do It Right with Maddi Waggoner

Hey, hey, you're listening to the Level Up Creators Podcast. I'm Amanda Northcutt, founder and CEO, and we're here to help digital thought leaders like you turn your expertise into rock-solid recurring revenue businesses. So glad you're joining us. Today's guest is Maddie Waggoner, the powerhouse behind Building Remote. She helps founders step out of the day-to-day grind so they can lead more, manage less, and actually enjoy things like vacation, parental leave, or even a full-on sabbatical. What a dream that would be. Uh, in this episode, we're diving into how to hire smart from the start. Think, clarifying roles before you even write the job description, spotting true rock stars beyond the resume, and building a lean, repeatable hiring process that frees you up to grow your business without burning out. Maddie, we're so glad you're here today. Welcome.

Thanks, Amanda. I'm so excited to be here.

Yeah, you and I were introduced last year. We've had a couple of conversations, and it's been so fun just to get to know you as a person and understand kind of your zone of genius and how you help your clients and You demystify this whole hiring thing, which a lot of solopreneurs and small business owners, entrepreneurs, however you classify yourself, this is a very intimidating topic. It feels like there's a lot of magic juju and unicorn dust and things like that in like the hiring process, but it's quite systematic, isn't it? And so we would love to get your take. Yeah, we'd love to. We're going to unpack that today and make sure we leave all of our listeners with some like major golden nuggets because you have so much wisdom and experience to share. Share. So, thank you again for being here. Let's start by helping our listeners get to know you a little bit better. Could you give us kind of the CliffsNotes of how you got from the early days of your career all the way into building, well, founding Building Remote? I was going to say building Building Remote, but yeah.

So, I actually had my first business at 19, which is actually, it was actually an acquisition. I bought it from someone else and I like to say it like that because people kind of, their ears kind of perk up, but I didn't know what I was doing. And at that time, it was a lot harder to find information. You know, these days we're using tools like, of course, Google, but AI's on the scene and it's so much easier to find things. So I ran that for a couple of years, did some other kind of odd jobs around marketing and business, and then I got into tech startups. And that was my first real remote job that I had gotten, that I found a company and pitched myself and got into that. And I learned a lot of things around operations. And that was the first place that I started doing hiring because at like most businesses, like most tech startups, small businesses, there aren't a lot of processes. There aren't a lot of standard ways of doing things. So I set out to create that. And as I went on in my career, I started picking up freelance side, uh, side gigs around, you know, my full-time job. Um, it just kept working with online businesses, all of it remote. And what I found is that there were so many opportunities and so much fear around hiring that if I could address them, that I can help these founders to achieve the goals that they have, because I love coming alongside people and helping them to achieve their dream, especially if it's, uh, you know, mission-oriented and helping to create freedom for people, both for in the business and outside of it. And if I can do that through different things like hiring and like you said, demystifying it, it makes it so much easier for all of them to achieve the places that they want to get to.

Yes. So was it that first remote job a long time ago that really kind of gave you the bug for figuring out the lifestyle architecture piece and like what's actually possible, um, outside of the, you know, traditional 9 to 5 going into the office? So what was your kind of your, where, where did the unlock come in that phrase? Or was that more on like hindsight after that job?

No, it was totally in that job because I took a course. It was a design education company. And so they were taking people who weren't designers and teaching them how to become full-time designers to change their careers. And I took one of their intro courses and I loved the experience so much. I reached out to them and I said, hey, I don't know if you need help, but I'd love to help you. And funny thing was, is they had just posted a job description, but on Craigslist in New York, and I live in Colorado. So totally worked out there. I ended up staying there for 3 years. I led our operations team and grew a whole bunch of different things there. And what I found, not only in working with the internal team, I had people on my team who were digital nomads. And I always like to joke with them that, uh, I lived vicariously through them. Because at that point I had a family and, you

know,

things that were kind of holding me down. And I loved encouraging them to do that. But not only that, all of our students, and we had mentors who were matched with students, they were all over the globe. And getting to work with different people in different places really instilled this desire for me to help people become more skilled at remote work and running remote businesses. Because there's so much more intentionality that has to come with it.

Mm-hmm.

And if you want the freedom, like so many people do these days when they start remote businesses or they're leading remote businesses, There's so many intentional things that you have to do in order to achieve that freedom. And I know you know this as well with the work you do.

Yes, that is so important. And again, I'm sure you're even more familiar with these statistics than I am, but I mean, in larger organizations, misfiring on the hiring, making bad hires is like the biggest expense for an organization. And that can tank a company. I mean, a bad hire in a small organization, you want to talk about like a fly in the ointment? Holy moly, the consequences of that are so far-reaching. But then in big organizations, when you don't have a hiring process in place and you're not putting the right butts in the right seats, the compounding effects of that— it's like interest in the worst possible way— are really, really detrimental for organizations. So, for— let's unpack it— for these solopreneurs who are drowning in tasks, they're spending probably a lot of time not in their zone of genius. They're spending probably a lot of time on minutia that should be Well, not done, deferred, delegated, automated, automated with AI and other pieces of technology. How in the world do you even start thinking about your first hire? How do you, how do you know when it's time? And then how do you actually start the process?

Yeah. So, there's a couple of things to think about with when it's time. A lot of people like to say you need to hire before you actually think you need to, which is totally true. A lot of people wait until they're, they feel like they're drowning. And if you can start looking for the kind of inklings of, I think it might be time for me to hire, pay attention to that. And if you aren't able to do that yourself, then ask either people on your team if you have team members, or if you don't have people on your team, ask people who are around you who are familiar with this kind of work. Like I do assessments with every client I work with to help understand where they're actually at. Because there are things like, if you are starting to grow your business and you are at capacity because you don't have time to stay on top of everything, you absolutely need to have someone else in your business doing the things that You don't have to be doing. And a lot of people feel concerned around, well, I don't know if I'm going to trust this person. That's why we have a process, and we develop the process in the hiring steps, but also when they come on in the training to help build trust and ensure that they're going to do the kind of job you want. And if you're in a larger company, something that I like to do is I recommend that founders do what I call quarterly momentum check-ins with their team members. And it's essentially my twist on the corporate performance review, but it's more growth-oriented. So we ask 3 questions. What's going well? What's not going well or what needs improvement? And what should we change? And it, we have the team member own that. So it takes pressure off of the founder to do all of the legwork, also gives ownership to their team. But part of that process is also the team member keeps track of their job responsibilities. So they can essentially take their job description that they were hired with. And as they go through the quarter, if there are new things that they take on, they just add it to that job description. In like a different color or something so that you can see the difference. And they evaluate that with the founder. And if you get to the end of the quarter and it looks like that person now has 2 full-time jobs, might be time to start looking at hiring. And you can do this as a founder too. And I have a resource that we talked about that I can share more about at the end.

Awesome. Okay. And I guess let's back up a step. Did I even ask the right question? You know, like, I guess maybe another question would be what pains specifically would a solopreneur or small business owner That's running a boutique coaching or consulting firm, like what are the specific pains that that kind of ICP would be feeling, uh, when they know they need to start looking or they should have started looking a couple of months ago?

Yeah. One big one is if you're feeling burnout, if you feel like you can't stay on top of things, um, any of those types of feelings. And I like to lean into the feeling side because sometimes it doesn't seem overly clear to you. You have to pay attention to where your energy's at. Because as founders, we are the visionaries, the idea people. And so it's really important for us to protect our energy. So that exercise I mentioned, um, actually walks through some of this process and calls out, what do you enjoy doing? What do you not enjoy doing? What do you procrastinate on? Which happens for a lot of solopreneurs. Um, and you know, what kind of things are you just not good at? Because I like to use this quote from a boss of mine. Her name is Jodi Yorg. She used to be a vice president at Yelp and, um, she was the CEO at one of the startups I worked at. And she used to say that you should scaffold around your weaknesses, build up your strengths and scaffold around your weaknesses. So if you're having a, if you have a long list of weaknesses, things that aren't getting done, um, that are getting in the way of you growing your business or increasing your capacity, or you're never able to take time off because of those things. All of those are symptoms of this problem that you are trying to do too much. And there's a certain level that you can say no to, but there's also a certain level that it's going to impede your growth and your progress if you don't bring someone in. So that's why I like to ask those questions and pull those things out, because it becomes rather than a Again, that feeling, we get it down on paper so they can clearly see, oh, this clearly is a role for someone.

Yeah, that's a great assessment. I'm excited to share that with our listeners. And that will be, of course, in the show notes and show description. Well, let's talk about when someone realizes, okay, I do need to hire someone. A lot of times the folks that I advise and work with try and put kind of the cart before the horse. And they also have very unrealistic expectations that they will be able to hire someone who is, or one, They go the wrong route. They're like, "I just need to hire a clone of myself. I need another one of me," and that is completely opposite to the scaffolding maneuver you're you're discussing. So one, you don't need a clone of yourself. How do you figure out who you actually need? And also just PSA, like the unicorn thing is just you can hire a very high level chief of staff that sometimes can do those things, but otherwise. You probably need help in 6 or 10 different functions of your business, and it's very unlikely you'd be able to find one person. So, okay, I'm a founder. I've had this realization. I'm burning out. Calendar's completely overflowing. Things are falling through the cracks. I cannot do another month's books, and my inbox is overflowing. Okay, so I'm at this place of overwhelm, barreling toward burnout. I know I need to hire someone. What do I do next?

Okay. So first we have to get clarity. So we'd go through these questions and get those things written down. Then we have to create a job description that will actually attract people. That's a big failing that I see where, um, in this process, someone might just say, I need help with X, Y, and Z, throw it up on LinkedIn, email me if you need something. And it's just going to create more chaos for you. So actually, let me back up a second. Um, one of the first things people need to do is understand this process takes You can't just get this done in a few hours. You have to be intentional with it and follow the steps in order to get the right hires. So, once we get that clarity, we can create that job description, and we have to also call out the things that make us attractive, because we, when we're looking for people, we don't want people who are just looking for a paycheck, just learning or looking to earn money. We want people who are bought into what we're doing and light up when we talk about the work we're doing, when we talk about the flexibility or that our team is collaborative, or even if you don't have a team. If you want to have a collaborative workplace, list that out. You know, call out that you are going to be growth-oriented, that you want to help them get to the next level. That's something that I do. When I, when my team members come on, I am very clear with them that I know that you might want to move on to other roles either here or somewhere else. I'm totally aware of that. I want to know what your goals are so I can help encourage you and move you and grow you towards those places. Not a lot of bosses will do that. So, even if you don't have things like typical health benefits, say you're hiring for a part-time, like, 1099 role, you can still call those things out because it's attractive to the right kind of people. So, we have to be intentional with those things we call out. And to your point a minute ago, if you're trying to hire a unicorn, you should have someone else who knows hiring or knows this field and have them look over the job description to make sure it's not too much, because that also will turn away really great candidates because they are aware of what their worth is. They are aware of what's realistic and aren't going to want to touch the things that they aren't good at because they have their own zone of genius. So getting really clear on that before you post, then posting in the right place, making sure that that's all covered. And some of that is related to, you have to know where these people live. In some cases, that's Reddit. In some cases, that's Facebook groups. In some cases, that's training programs that have a job board where you can submit to them, or you can just reach out to them. And if they don't have a formal process, sometimes it is on paid job boards, but even with those, that can be bring not the best candidates because now there's so much attention on those. And they're also often scraped by other job posting sites. So you have to be aware that maybe they're not the best place to look. Um, and then making sure that you're really covering a lot of process in the rest of it. So having a formal job application, don't use email. This is a soapbox for me because people don't understand that when people email in, they're not getting the same information from each candidate and it's not going to be easy to process through all of them. So it needs to be really structured. So having an application process, having a system. I've actually built my own custom system for this because I was so irritated by people using emails to collect, uh, applications.

Mm-hmm.

That I've, I built this whole thing. Um, and then within that system, there's also structure around interviews as well. I use a rubriking system because I've seen so many clients that when there wasn't structure, they kind of went off of what felt right or who they best vibed with, but it wasn't always the best candidate for the job. So I use a rubriking system within that tool to make sure we're checking across their responses in the questions. And then the last piece is to make sure that they put in time around onboarding. One of the easiest ways to help prepare for a new hire, even if you're not ready to hire yet, is just record with Loom the things that you're actively working on that you want to hand off to that person. Because then when they show up, you can just give them the list of Loom links and say, please go create written documentation on these things. It gives them ownership over that. Quick win because you've already recorded it. They have all the material. They can then run with it. It's a great first task for them to do in their first week.

Yes. I love that you're talking about onboarding. That's so very, very, very important because as the business owner, we have all the context and it lives in our heads. And that's a big problem. So making sure that you've got standard operating procedures, even if those start with a Loom video to your point, um, and your onboarding and, you know, role and responsibilities document and everything like that, that you hand over to this person that, uh, you have external knowledge and that you are not holding context and expectations in your head. Because remembering that, especially if you've not ever hired someone, people cannot read your mind. They cannot read your mind. Nobody cares about your business as much as you do as the founder and CEO. No one on planet Earth is as bought in as you are. No one is going to step up to the plate day after day and work as hard as you are at that. So what are some common pitfalls, I guess, maybe yes and what I just said, or if you have a different opinion, that's great. Um, may, you know, 3 to 5 most common pitfalls that, uh, founders fall into when they're trying to make their first hire?

Fear is the first one because oftentimes when they're a solopreneur, they're running things by themselves. They are afraid of how much it would cost, or they're afraid that they're going to hire the wrong person. And so So, when I work with someone like that, I address those first things. I say, okay, what are you afraid of? Or what's gotten in your way in the past? Well, you know, I had one person who told me that they tried hiring 5 different assistants off of Upwork. I'm like, okay, let's unpack that. How do you feel about that? And I've, I've had clients tell me, oh, this is like a little therapy session. I'm not a therapist, but I do ask.

Business

therapy. Yes, exactly. I do ask a lot of those types of questions because having been in all the companies I've been in, especially with the tech startups. The way that the founder feels about things impacts every other decision in the business. And I want to make sure, excuse me, I want to make sure that we address those things upfront because it will impact the entire hiring process. And in some cases, people will self-sabotage. So, that's one of the first things that I want to call out. And it's often hard for people to really evaluate that the same way, like on their own, unless they're really self-aware. So that's one of the first things that I look at. Um, like I said earlier, not taking enough time is another big one. And then not following process. So I laid out that process of all the different steps of what needs to be done. And obviously there's a lot more to it than I covered in just a few minutes. But, um, if you don't follow a very specific process and make sure that you're improving each time, make sure that you're covering the right types of information, you're going to find that you're not going to get the right types of hires and you're going to be continually disappointed, which is why I've developed this process over years and years and a lot of different hires. And iterations, and I even will ask sometimes ask for feedback from candidates of how was this process? Did you feel any? Was there anything that felt clunky to you? Was there anything that you had questions about? And I use that to then improve the process. Do the same thing with clients as well. If they feel like I once had a client who said, "I feel a little in the dark when we." I know that the job posting's up because you let me know about that. But like we've been so communicative, and then there's just silence. So I now have a process where I'll update them on hey, we have this many applications. We have this many applications. Or hey, we're looking at we've got some really good candidates. candidates in. I'm excited for you to talk to some of these people. Just even that touchpoint has helped to improve the process overall.

Nice. Yes. Proactive communication. Yeah. And overcommunication, I think, is really important. Okay. How do you interview effectively? Let's say you nailed the job posting, you inject some cultural elements and make sure, you know, you're testing, you're stress testing for values alignment. You're having people submit their application in JV and not through email. They're, you're having people fish in the right pond, so to speak. So, they're looking for candidates where qualified candidates are potentially hanging out online. So, now we've got 10 people, we've got, you know, 10 JVs and applications to sort through. So, let's start there and maybe take us through, I guess, your interview process, your POV on how we get from applicant to offer.

Yeah. Well, let me start with, since you said a number, I just want to speak to that. Most of the time I see hundreds of applications. In a couple of cases, we've had thousands. So, normally we trim that down. I tend to try to do around 10 first-round interviews. So, if you're having 10, then you might want to expect that you— if you have 10 applications, you might want to expect that you might do maybe like 3 first-round interviews. Just depends on the quality of those candidates. But when you're preparing for interviews, there's a handful of things that I like to do. One, make it easy for them to schedule. There's a lot of scheduling tools these days. Some are specific to hiring. I don't think you need to use those ones specific to hiring. Just use what you already have, but make sure it's easy for them. Make sure there's a lot of communication. And then when you're preparing the actual questions, I like to look at there as it being 3 parts of the picture of the person. So, we have the application, first-round interview, second-round interview, and then if you do more interviews or a project or something that adds another piece to it, but at bare minimum, those are the 3 that I do. And we have to look at it holistically. So, the application itself should be asking more screening-level questions to make sure that the people who are applying have that level, at least at a bare minimum, of experience. And then I also like to check for things like drive and growth, like mindset, because a lot of things can be learned by those type of, types of people. So, when we go into preparing for the first-round interview, we want to consider the types of questions that we need to ask next. So, that's just a different level deeper on certain topics that maybe we didn't cover in the application. And we want to make sure that we're getting granular in some of their past experience, especially because people use AI these days. And I see it a lot more in applications recent, more recently in the last couple of years than I have before then.

Yeah.

So, you have to prepare that they might have some AI-written questions that maybe actually aren't true for them. So, I like to change the questions so that they're more focused on what have you done versus like, what is your philosophy? So, um, those are some things I like to do there. And then, excuse me, as far as actually running the interview, make sure that you're keeping an eye on time. And I always say at the beginning, I like to, what one of my friends calls level setting at the beginning of the interview. I say, let me run you through my little spiel real quick. This is how much time I like to spend on asking you questions. And I'll save this time for questions that you might have at the end. Um, just so they're aware that you're going to be asking questions. I also share that information when they book the call. And then keeping an eye on time. In some cases, you might need to drop certain interview questions if they're a little bit chatty, which can also be something for you to keep in mind of, are they concise? Are they to the point? And then when you get to that, um, like last couple of questions, I like to say, okay, I have one more question or two more questions just to kind of keep them on track with where you're at with the time. And then, um, allow them that time to ask questions and always take notes. Because again, like I mentioned earlier, I have this rubric system. It's important to keep the notes, um, For each question that they answer so that you can go back and rate it, because it'll automatically score people. And that's generally what I do, at least for first rounds. And then second rounds is somewhat similar to that. And obviously, there's a lot more we can go into around what types of things do you look for when people answer questions. A lot of it is, what's their mindset? Are they growth-oriented? If I ask questions around how you work with people, are they blaming others? There's a lot of more soft skills that you can dive into when you're going through interviews there.

Yeah. Ask them questions about their past bosses. That's always a fruitful discussion.

Absolutely.

Yeah. What's the saying? If they'll, they'll do it with you, they'll do it to you. But sort of like if they're talking smack about a past boss and like blaming, like you're talking about other people, that is indicative that they are looking for a scapegoat and maybe not the most accountable potentially. Obviously there are exceptions to every rule, but yeah, it's very interesting. The interviewing process is such a psychological extravaganza almost because, you know, you ask one question, but, you know, a skilled hiring manager is looking for 8 different things in that response in terms of, as you were saying, concise, clear communication. Can this person form a thought, an original thought in their head and speak it out in a way that is professional, relevant, and clear? And we're looking for demonstrable track record of success in the jobs that need to be done at this new role. And What role that they played on their team and how their team members viewed them. And I find that the more specific questions you ask, digging into like stories, unless they're literally a pathological liar, it becomes harder and harder to lie the more specific you get and the more details that you ask for. How do you feel about figuring out how much to pay someone? Obviously, it varies by role, but like, what's the process that we can kind of hand over to our listeners today to be thinking about how in the world to pay someone equitably?

Yeah, I'm big on paying someone equitably. I've had people approach me and want me to hire them, and it's been a fit in the past. And there are times where I've told them they need to charge me more. So that's just my philosophy of, you know, this, this work is worth more than what you're charging. So there's so many tools available these days. You can do what's an average salary if you're hiring full-time, look into different states. Some, in some companies they have Like levels just that are based off of general locations. Some are just, this is flat what we pay for this role. And if you want to increase your salary, then you need to be promoted or something. So, you have to decide compensation, like, strategy, which is not my area of expertise, if you want to go, like, really deep into laying something out for your company. But do at least some research. Ask some people who are in that role if you have them in your network. Mm-hmm. Don't just come up with a number off the top of your head based off of your budget. You need to be informed on what's actually appropriate because going back to what we said earlier about attracting the right candidates, if you're not paying enough, the great rockstar people that you want to bring onto your team, they're not even going to apply. So you won't even ever talk to them. And then they will have a negative opinion of your company, which obviously you don't want. In some cases, it's better for you to hire for, if you're doing say hourly, less time of that person or less scope so that you can get that higher impact person, again, depending on what your needs are.

Yeah, that old saying, you get what you pay for, still stands. That's very—

Absolutely.

That's very important. And if you are trying to go with a budget pick, there's another phrase I really like. It's good, fast, or cheap, pick 2. And I've yet to find an instance where you can get All three. So that's really, really important to understand what your priorities are and knowing that you get what you pay for, and that if you hire at a higher level, your life is going to be a lot easier and a lot better than if you hire downmarket and have to do a lot of training oversight. All of your worst nightmares about hiring and about bringing on and fears to your point earlier, Maddie, about bringing on team members are going to come true. It's almost a self-fulfilling prophecy if you. hire downmarket and you do not have experience in leading and managing a team and holding people accountable and rowing in the same direction and setting goals and effectively delegating and creating standard operating procedures and setting expectations and stuff like that, you are setting yourself up for failure. And again, that self-fulfilling prophecy of everything you've ever feared about hiring. Um, so yeah, I'm a big fan of—

Exactly.

Hiring upmarket, getting what you pay for, and enabling people to achieve their full potential as a professional. And I love that you also do, you know, career pathing and try and help people even as contractors. That's a very human thing to do. And a thing that female leaders frankly do quite a lot, and I think is really, really awesome. So that's a great tip. And even if you can't pay as much, if you can provide other benefits like career pathing introductions, Space to learn new skills. You know, those are really valuable things. There's, I think, different levers that you can pull. Um, I'm actually using ChatGPT Deep Research to, uh, for comp plan research lately. Have you played around with that?

Not specifically on comp plans, but a lot of other things. Yeah. Um, there's, there's really no excuse for not being informed, at least to some level these days, because we just have so much, um, information at our fingertips. And if you ask the right kinds of questions, again, like you were saying with interviewing, same thing with ChatGPT. If you've gotten really good at prompts, it's similar for interviews. So just use that when you're looking into the numbers. And, um, there was something that you said earlier about don't hire downmarket unless you have experience and really enjoy managing and like helping people to grow their skills. That is so important. And if you're afraid of managing or afraid of giving feedback or any of those things, that's something to be very aware of when you're looking at hiring, because that's something that you need to develop as a skill. And you don't want to say, if your business is just really exploding, you don't want to bring on like 5 really junior people because you're going to have to be spending a lot of time coaching them. There's this whole concept of when someone is coming into a new task, they have low maturity in that task. And so, as they get more experienced with it, or if they've been working in it for years, then they're way more able to handle things on their own without you being involved. And I just don't think a lot of people pay attention to the time investment when you're bringing someone in that's more, like you said, downmarket.

Yes. Yeah. And for anybody that's new to managing people, there's a framework that I really like. And this is a riff off of Jim Collins. He's one of my favorite business researchers and writers. And, oh, I hope I'm attributing to this, this is the correct person to attribute this to, but we enable professionals to achieve their full potential and have high job satisfaction and intrinsic motivation in work. When we give them the opportunity to achieve mastery in their field, have autonomy, no micromanaging, but with clear expectations, and we give them purpose in their work, they feel like they're doing something. And that goes back to what you said at the very beginning of our chat today about making sure that you're testing for culture fit, values fit, and putting that right at the top of that job description. That's so very, very, very important because if your employees or contractors, agencies whoever you're using get up and they hate what they do every day, they're gonna do the bare-ass minimum. Bare-ass minimum. Exactly. It's probably gonna be pretty low quality. Uh, so I like that mastery, autonomy, purpose, and I've added on another A and a P, uh, appreciation and pay. And I put pay really at the top because if you can take care of the money piece, then your team members are much more relaxed. Happy. You've reduced stress in their household also, which is a big thing. If they're constantly like, shit, I'm not making enough money here, I've got to go like find a second job or constantly be looking for another job that is higher paying. But if you can just take the money piece off the table, that lets our back brain relax a little bit, that lizard brain that's trying to protect us all the time, and lets us step into our front brain, the human part of the brain that's spent a lot of time evolving, getting into a more creative, space and like productive flourishing is kind of like what we're going for there. Um,

I love that. That's great. Anyone who's listening definitely needs to pay attention to what you just

said. I need to figure out the acronym that's right. Cause like the MAP, MAP, but it's like MAPPA or it doesn't matter. But, um, that's a framework that I've used, uh, for a very long time, just, uh, in-house at Level Up Creators and the other companies that I have worked with and led. So, okay, let's talk about lifestyle architecture and the role that hiring the right people, putting the right butts in the right seats has to do with lifestyle architecture. Because Maddie, I mean, one of the things that really drew me to you and intrigued me about your positioning in the market with your own business is you help founders go on vacation, take parental leave, and take sabbaticals. And wow, you know, that feels like an absolute pipe dream, frankly, for a lot of our listeners who are Doing everything and keeping all of the plates spinning. So, tie the— draw the through line here from hiring and what it takes to kind of like stand up those systems around you. What has to be true in order for a founder to actually take a freaking break?

Yeah, yeah. It's a great question. Thank you. I like to draw this illustration and essentially imagine that you're a founder when you're a solopreneur and you're just one dot. And then you add someone to your team, there's another dot, and there's a line between the two of you because you work a lot together. And then you start to add more dots, and there's more of these lines going straight to the founder. And when you have this whole circle of dots around and all these lines just going to the founder, that's where you feel incredibly burnt out, and there's no possibility for you to be able to take time away. So, part of this is actually around how you build the culture and how you build relationships and collaboration between your team members when they come on. So, the picture that we actually want to have is all of these dots around the outside, but those straight lines are going to the other They're dots on the outside. They're collaborating. And then there are dotted lines going to the center person, basically illustrating that these are FYIs, these are updates. They're just kept in the loop rather than being really core to completing work. That's the kind of picture we want to develop. And there's so much of this that when you're bringing on team members, you have to give them things out of your brain so they can run. And then when you bring on new people, utilize your existing team members to onboard the new people. Create onboarding buddies, just assign someone to that role, bring them in, have things like lunch and learns. Where they learn and teach and encourage one another, so it's not just you. And if they start to trust that the other team members can help them make decisions, then they can go to those other people as well instead of going to you. You have to start removing yourself from the process early on in order to get to that ideal state easily anyway, or more easily. If you're in a place where you're in that, you're that center dot and you have all these lines going to you, you have to start actively working on teaching your team to take ownership and make decisions without you. For example, I've worked with a number of different founders where their team will come to them and say, what should we do? And my default answer— this is a really simple tool— when they ask, just turn the question around back on them and say, how would you approach this? How would you solve it? What would you do? OK, go think about it and come back to me, and I'll give you feedback. It turns into you being the problem solver to you being the coach, which does take time. But if you want to be able to take time away, you have to do that. And I actually learned this really deeply in my first startup because Um, when I was working there, we, uh, were just kind of chugging along and doing pretty good my first year. And then years 2 and 3, I essentially had a new job every single quarter. And so, I got really good with learning what the work was, documenting it, and then hiring and training new people into that role. So, essentially, I handed off my job to 8 different people over those 2 years. And during that time, we grew— 8? 8 times. We, we grew revenue by 6 times. during that time period. And the CEO, we had a team of 20 at the end of this, had taken a month completely disconnected, just away from the business. It's totally possible, but they had done a good job, and I had partnered with them to disseminate information so we could make decisions in his absence. And we practiced that for a while before he left, worked really smoothly, and he came back really refreshed after having run this business pretty, you know, He was pretty involved for 5 years or something before that. So, that's how you can start to do that if you're currently in this place. How am I possibly going to, possibly going to be taking time off? Start to enable your team. And if they aren't the kind of people that you can enable that aren't performing well, you need to be having conversations and helping to see, are they in the right role? Could they potentially move somewhere else? Or are they no longer a fit for your stage of growth that you're at right now?

All right. I want you to just drop your microphone and just walk away from the camera right now. That is an incredibly potent visual, and I've never heard it explained that way. So, I'm going to repeat real quick, make sure I understand. So, you as the founder are the nucleus of the business. You're in the middle. And if you wrote down everything it takes to run your business on a whiteboard, right? And then draw a direct line in everything you're responsible for, right? If you're a solopreneur practitioner, It's you. It's on you. And so, what you want to do is reduce the number of straight lines to you by putting basically armor kind of around the nucleus that is you and get people between the thing that needs to be done and you. And you best enable and empower your team members to do that by enabling and empowering them by asking this really magical question, not letting them, not responding to, what do I do here? But turning it back around and having a thought experiment and exercise and coaching opportunity with them by saying, how would you handle this? Or what do you think that we should do? I mean, that's just like incredibly powerful. And we use something called an AOR chart in our business, an area of responsibilities chart. And you can keep that at like a 35,000-foot level and just say, you know, marketing, sales, customer success, customer service, technology, product, pricing, right? You can have it really, really high level. Or you can get down closer to the ground floor and talk about, you know, individual functions within each of those areas of the business. So, everything that it takes to run Level Up Creators, which at this point is a lot, is on this AOR chart, area of responsibilities. And then there is a DRI, directly responsible individual, next to each and every one of those functions. And each of those functions has a backup person. I'm big on nobody, there's not a single person in this organization where someone cannot do their job so that everybody can go on vacation. That's a huge piece of this as well. And then we have standard operating procedures associated with that area of responsibility and a health metric and standard operating procedures associated with that area of the business. And so, like, that's pretty damn sophisticated. And it took me like 20 years to figure out what our operating system is, which starts, I mean, we have a whole thing for hiring and onboarding and coaching and upskilling and career pathing and all those kinds of things at this point. But that is, I think you took my very linear area of responsibilities chart and made it into a very powerful visual. And so, it's like, you know, I teach founders to spend at least 80% of your time doing the tasks that only you can do and that provide the highest amount of leverage for the business. Otherwise, you need to think about what you can remove from your plate, what you can defer, you know, do later, what you can delegate, automate with technology or AI or a human. As it were. Uh, and then it's really just what's left after you kind of like stress test everything on your to-do list. Um, that was very helpful. Thank you. I feel like those are enormous takeaways that our listeners find very, very helpful. Really just the visual there. Do you have a visual? Because I feel like this needs to be—

I was going to say, I have a graphic. I can share that and we can put that in the show notes.

But yeah. Yeah. I would love to throw that up on LinkedIn. Yeah.

Yeah. You, you just touched on, um, the intentionality and the time that it takes to create all of these resources. And that also is something that people tend to be fearful of, of, oh, I want to give this information to my team, but that's going to take me so much time. It really doesn't. And if you're thinking about that you have to write everything down, there are so many tools these days like Loom where you can just record yourself talking and then give it to your team. Because when you give it to them and ask them to create the information, most of the time they're better at doing that than you are, for one, because again, you're hiring for people who are not the same as you and are typically more organized, but you're also giving them ownership. Over, they create the documentation, they're responsible for all of this information, they're responsible for making sure that new hires are— I mean, this is part of my job is making sure that new hires go through this documentation, that if they have any questions, they can ask someone else on the team about that type of information. And if they're asking the person who created the documentation, then they can identify where the holes are. They can come back to you and ask some clarifying questions, then go update the documentation. It's this whole cyclical thing about how do we constantly improve? How do we constantly improve and ask questions? And if founders are not willing to spend the time to just start sharing information, that's something that we have to address as well, because your team's going to be in the dark. They don't think the same way that you do. Nobody does. Even if you've been married to someone for a really long time, I can bet that you have disagreements on what you think you should do in certain instances, right? My husband and I talk a lot and agree on a lot of things, but, uh, There are certainly things that we disagree on, and it's the same thing in your team. So, you have to pay attention to how you share information. And when my assistant joined recently, she was asking me questions around, what, which offers are we focusing on? Which direction do you want me to be? And so, I had to, I hadn't taken the time to be very explicit on that particular piece. So, part of when we're talking about onboarding, you have to make yourself available and you have to ask questions to encourage them to share whatever gaps they're seeing. And I love to use, like, I'm a third party. I can come in, I can see things that you probably don't see because you're used to how things operate. If you have new team members coming in, they're similar. I like to say that they have fresh eyes. And you should encourage them to say what, to share, what are you seeing that is not working smoothly? Or is there anything that you've seen and it just, what, what is this, guys? What are you doing? And if you encourage that behavior at the beginning, not only can you take advantage of their fresh perspective on it. You also encourage them that this is the type of environment we want to have. We appreciate feedback and sharing so that we can all be better. And if that's the type of company you want, you have to be very proactive with the questions you ask too.

Yes, yes. Oh, that's amazing. And yeah, Loom videos, they're a big, big unlock. And I know Loom has a tier where you record a video and it can create a standard operating procedure for you. You can also just grab grab the transcript, frankly, from the Loom video, throw it into ChatGPT and say, hey, make an SOP for me here. But I love that just immediately giving ownership over to your team. And because when you're recording a Loom video, you're just doing what you had already been doing for a long time, right? You're, you're not giving yourself any extra work. You're just recording yourself and you are thinking out loud so that you can delegate that process as quickly as possible. And that really is the trick. Too, isn't it? It's just think out loud, record yourself doing it, hand it over. It's a trust but verify kind of exercise though. You must keep your team members accountable while not micromanaging, and you have to kind of like straddle that fence. But I love to record a Loom and then watch them do the process. Maybe they just record a Loom of them doing the process, and they're maybe asking me questions in that, in this. So a lot of this can be done asynchronously. Which is very convenient. And then, I typically have folks go through a process 2 or 3 times, and I'm verifying and testing it, or whoever their manager is at this point will verify that they've got it nailed, and then we hand it over. But that doesn't mean that you stop using the standard operating procedure. You have your team, oh, I've got this process memorized. No, standard operating procedures are there, just like productized services, to ensure consistent excellence across the board. And SOPs also help us free up our brains to do our brain's best So, we want to minimize thinking about the minutia, not just for us as founders, but for our team members as well, because we're hiring smart, intelligent, capable people, and we want to elevate them to their full potential. And we can't have them mired down in the minutia, or they will not help your organization as much as they potentially could if they're constantly worrying about little details. So, documentation is, I mean, that's kind of the, that's the big unlock, right? Documentation and trust but verify. Exactly. Get you to that vacation.

Yeah. And, you know, it also de-risks your business too. If you're leaving everything up in your head and you do have a team, if something happens to you or say, you know, I hate to talk about these things because they're sad to think about, but let's say you lose someone who's very dear to you. You don't want to have to stay in the business because everything's in your head. And that's even, you know, removing the idea that something could happen to you. We want you to be present in these places where, and a lot of people are like, oh, that's not going to happen to me. I've personally experienced 4 different deaths of loved ones in the last 18 months. So don't assume that nothing's going to happen in your life. So share, getting this information out of your head when you're in a good mental place prepares you for the times when you won't be, or if you lose a team member for whatever reason, like you said, you know, your team is able to step in. If you have documentation and SOPs on how things should be done, anyone can pick it up, even if they, say, someone on your team leaves right after a new person has come in. At least you have the documentation, even if they haven't had the time to get up to speed on the process. It's so, so important to have those things written down, recorded, at minimum recorded. Like you said, you can do so much with it. But you have to take the time to do those things. And like you said, trust but verify. One of my client teams, I recently was having them record training videos multiple times a week, and they just had to submit it in their weekly reporting. And that was something that they were working towards for a larger goal. And now we have all these resources that in the case that they take time off and someone else needs to step in, it's just there.

Amazing. Yeah, it's like playing offense well so you don't have to play defense because, yeah, life

happens.

Life be lifin' and throws curveballs at us all the time. So, this is a very good, creates kind of a defensible position for your organization as well. Like, it cannot, if you get hit by a bus, what happens, right? So, can it actually run without you? Maddie, thank you so much. You've been so generous with your wisdom and experience and knowledge and time. So grateful that you were able to come and share with our listeners today. And tell us just a little bit more about the resource we're going to share in the show notes and show description.

Yeah, so it's called the Founder's Focus Assessment. Essentially, it's just an exercise that walks you through essentially brain dumping everything that you do and you handle, and it helps you organize based on the things that are your strengths that you enjoy and helps to pull out the things that you avoid or procrastinate on or just don't like doing or aren't good at. And it helps to create some clarity around, should we hire for this? Is this stuff that maybe we don't need to be doing anymore? And most people don't take the time to do this type of exercise, and you can do it consistently. If you want to do it quarterly through seasons of growth, that's essentially what I did when I was changing jobs every quarter. So, highly recommend that you save it as a resource. Of course, it'll be linked to your free resource. Just something I like to share with people because it'll help give you clarity on if it's time for you to hire and what types of things that you need to hire for.

Nice. What an incredibly valuable resource. Thank you again, Maddie. We're so glad to have you. And to our listeners, thank you so much. We know that your time is precious and we appreciate you sharing some of yours with us today. If you are a subject matter expert or thought leader looking to build a customized business in a box with a 5-figure MRR guarantee, head over to mrraccelerator.com to learn more and be sure to follow me, Amanda Northcutt, on LinkedIn for daily insights. That's it for today. We'll see you next time on the Level Up Creators Podcast.