Know when to delegate control, as strategic hiring isn’t just about growth—it’s about mastering the art of liberation. In this episode, Kendra Perry ponders the ultimate question: “Who Should You Hire First in Your Business?” She discusses when to start building your team, emphasizing the importance of timing and strategy. She also shares her journey as an entrepreneur who transformed her business through strategic hiring. Kendra provides a roadmap for entrepreneurs at different stages of growth, explaining the telltale signs on when it’s time to outsource and on identifying tasks ripe for delegation. Tune in now!
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Who Should You Hire First in Your Business?
I want to talk about hiring, which I love talking about because it’s one of the ways in which you can build a lot of freedom in your business. I’m all about building businesses that provide you with a ton of flexibility and freedom. An important way to do that is by hiring the right people for your business without over-hiring or hiring too many people. A lot of people will ask me, “When in your business is the right time to start hiring?” Truthfully, I think it depends on you, your business, your goals, and how well your business is doing.” I can tell you when is not a good time to start hiring.
I had a woman reach out to me on Instagram. She was brand new. She hadn’t started her business. She’s like, “I’m looking for someone to help me build my business and get my team hired.” I was like, “You don’t even have a business. You have no business hiring a team.” There’s a lot of bad information out there. There are a lot of coaches, gurus, or experts who tell you that you need to get this team hired before you start the business. That’s not true. That’s going to make you stressed out. At that point, you don’t even know enough to hire.
In order to hire people in your business, you usually have to train them. You’re the expert. If you don’t even know what your business is doing, that is not a good time to hire people. You can start outsourcing small jobs in your business as early as possible. This is something that I push my students to do because they’re trying to do everything in their business.
What you’re going to learn, or what you have learned if you’re more established, is that there’s a lot of s*** to do in your business, and it’s impossible to try to do it all. When you try to do it all, you end up working crazy hours. We get into our business because we want flexibility. We want to make our own hours and freedom. When you’re trying to do everything and wear all the hats in your business, what happens is you are working 40 hours a week or more.
I believe that you should start outsourcing small jobs as early as possible, because usually in the first couple of years of our business, we’re not making a huge amount of income. We don’t want to be spending a ton on hiring, but we can start to outsource small jobs. This can help you grow a lot in your business and make more money in your business because it frees up your time.

If you’re spending all your time bookkeeping, scheduling social media, or answering customer service emails, you’re not going to be able to build the business. Business-building activities are critical to your growth. These are things like creating campaigns, marketing, social media, content, webinars, and building your program. If you can’t do those tasks in your business because you’re busy doing all the admin stuff, your business is not going to grow. What you’ve done is you’ve created a job for yourself within your business.
A lot of people will ask me, “What are these small jobs that I can start outsourcing?” Something you can do is called the zone of genius exercise. I didn’t come up with this. I honestly can’t remember who did shout out to whoever created the Zone of Genius exercise. You can open a notebook and create a quadrant. It’s a little T with lines. There are four quadrants. In one quadrant, you can have the zone of incompetence. In the next quadrant, you can have the zone of competence or competence. You can have, in one of the lower quadrants, the zone of excellence, and the final quadrant, the zone of genius.
For the zone of incompetence, what you can do is you can write down all the different things that you do in your business that you hate. These are things that you’re bad at and things that you hate. You know someone else could do a lot better than you. You can write those all down there and move on to the zone of competence. These are activities that you’re okay with, but you know someone could do better than you. You don’t hate them as much as the tasks in the zone of incompetence, but you dislike them, and you know you’re not the best at doing them.
There’s the zone of excellence. These are things that you are good at, but you don’t love doing them. In your zone of genius quadrant, these are the things that you are uniquely good at. These are things that you love to do and give you energy. This is going to be things like coaching your clients, building your program, or speaking.

The things that you should start slowly outsourcing are everything that you wrote in the zone of incompetence. There may be certain things in there that you can’t outsource. One of them might be sales calls. You can hire someone to do your sales calls, but it’s not something that you should outsource until you’re making good money in your business because it’s a big expense. In there, it is creating social media content. I believe that you need to create your social media content, but there are aspects of social media content that you could outsource, like scheduling or the design side of things.
The reason why we want to start to outsource the zone of incompetence is because these are soul-sucking tasks. When I think about productivity, I think of it as energy management. We can’t get more time in the day. We can only better manage our energy. If we are spending our time on things that we hate and we’re bad at doing, that ruins our energy for the zone of genius stuff, the things that we love doing, and that light us up. I truly believe that having better productivity and getting more done is focusing on the things that we are good at.
If you’re newer in your business, you might not be able to outsource everything you don’t like but know that can be one of your goals. I’ve outsourced everything that I don’t like doing in my business to the point where the only things that I work on in my business are content creation, supporting my students, and updating my programs. That’s all that I do.

For example, if content was one of your zones of incompetence, you’re like, “I’m not good at this.” Know that you can get better at this, but maybe you hire someone to schedule all your social media or design your social media because you are sick of spending all your time in Canva, and you are not good at design, like a lot of us. You can write your content, pass it over to someone to design it, and pass it over to someone to schedule it, which is what I do with my content because I don’t want to schedule and design anything. All I do is write my content, which means that I can do a month’s worth of interim content in usually 3 to 4 hours.
A good example is on one of our HCA coaching calls, I had a woman who was a little bit older. She’s like, “I’m stuck in the tech. I feel like it’s preventing me from moving forward. I can’t make any progress.” I said, “Maybe you should hire a tech VA. There are virtual assistants that will do the tech for you.” I have one, her name is Kim. She’s amazing. I hired her in the summer. I did all the tech in my business up until summer, and I’m going into year nine. I should have hired her a long time ago. It’s been amazing. She takes care of the tech. She makes sure it’s set up. When things go wrong, she takes care of it. It’s amazing.
When you think about my business, I have a high, multi-six figure business. I generate a lot of revenue. I have quite a few students. She does about 5 to 10 hours a month in my business. It’s not that much. You can imagine that your business is a lot smaller than mine. It wouldn’t be that big of an expense. In the case of this woman, she isn’t making any progress in her business. I was like, “You can commit to learning the tech and have grace for yourself that it’s going to take longer, or you can hire someone and start moving forward.” I believe she decided to hire someone. She decided that the expense was worth it so that she could start making progress in her business.
Another one of my students was struggling to do her social media. She would procrastinate. She wasn’t making content. That was holding her up in her business. She’s someone who came from a corporate job where she had deadlines and people holding her accountable. I said, “Why don’t you hire someone to schedule your social media content for you? You’re going to have a deadline. You’re going to tell this person, ‘I’m going to have this content for the 15th of every month for the next month.’” Having someone to hold her accountable, and hiring someone who was expecting her to give her the stuff to schedule on a particular date, made her take action.
Sometimes, hiring out these tiny little jobs can help us be more productive, especially if you’re someone who does come from a corporate job where you’re used to having deadlines and you’re used to someone holding you accountable. A lot of times, in your business, no one is holding you accountable, but when you start bringing people into your business, it starts making you more accountable because people can’t do their jobs until you get them the stuff.
These little jobs, maybe one-off jobs, or people who are doing minute jobs in your business, you can do that early on, especially when you’re starting to notice that you’re spending so much time on something you hate and it’s not moving your business forward. Sometimes, hiring is the only thing that’s going to bring your business forward.
In terms of hiring your first ongoing contractor, you should do that at the $80,000-a-year mark to six figures. I hired my first virtual assistant at about $80,000. I could have done it earlier. There are a couple of different perspectives on this. Personally, the first major hire that I did was a virtual assistant. The great news is that with outsourcing, it doesn’t have to be expensive. You can outsource to all different countries where the exchange rate goes far. My first virtual assistant lived in Peru, and I paid her $9 an hour. It was affordable. I believe she did about 3 to 4 hours a week for me. That was 3 to 4 hours a week extra for me where I could work on my business or take some time off.
For a lot of people, the first person that they will hire is a virtual assistant. A good move for someone, especially if you are at that $80,000 mark, you’ve probably at that point, where your business is more established. You have some systems, but if you’re not an organized person, I recommend hiring an online business manager for a one-time project to come in and organize your business and hire a virtual assistant to do the admin tasks for you. That’s what I would recommend. This is something I wish I had done.
An online business manager, if you don’t know what this is, is someone who manages the day-to-day in your business. Think of it like if you owned a restaurant and you hired a general manager. They come in, they deal with the staff, they deal with the schedule, they make sure everything is running well, and manage things well when you’re not there. That’s what an online business manager is. I’m going to refer to an online business manager as an OBM moving forward.
An OBM is a great hire in your business once you are way more established. For example, in my business, I have quite a few contractors and we have launches and events. My OBM’s name is Elise. She organizes all those things for me. When our contractors have questions, they go to Elise and they don’t come to me because I don’t want to be a manager of people. That’s why I brought in Elise.
A lot of times, it doesn’t make sense to hire an OBM when you’re at the $80,000 to $100,000 mark. This is something you would hire well down the road in your business. They are more expensive. It’s an expensive hire. It’s not something I would do at the $80,000 to $100,000 mark, but you can hire them. There are a lot of OBMs that will do a one-time project where they’ll come in, they will organize your business, set up systems and processes, and set up to-dos and instructions for everything so that it’s easy for you to bring someone a virtual assistant into your business.
I want to make the distinction. An online business manager is a manager. They think for themselves. They make decisions in the business. They tell people what to do. That’s not a virtual assistant. A virtual assistant takes orders from you. They do what you tell them to do. A virtual assistant isn’t someone who should be making decisions in your business.
If your business is unorganized and someone comes into your business and it’s all over the place, it’s going to be hard for a virtual assistant to do a good job. This is something that I came up against when I hired my first virtual assistant because up until that point in my business, everything was in my head. I didn’t have anything written down. I realized that if I was going to hire someone, I needed to document the things in my business that I wanted them to do. I couldn’t say, “Schedule my social media.” I had to say, “We use Later.com to schedule our social media. This is how you use it. These are the deadlines around it.” You can’t throw someone to the shark, especially not a virtual assistant.
When you’re at that $80,000 to $100,000 mark, you can find an online business manager, a one-time project to come in, set up your business, and put everything into a project management tool like Asana, Monday, or Notion. Once that’s done, everything will be streamlined and it’ll be easy for you to bring a virtual assistant into the business because you can be like, “You’re going to do this. Here are all the processes for doing that” A virtual assistant can do things like answer your emails. They can respond to customer inquiries. They can onboard and offboard your clients. They can schedule social media. They can do things like that.
Something that I’ve seen a lot, especially for established coaches who are at that $80,000 to $100,000 mark, is that they’re hesitant to outsource or hire because they say, “I’m a control freak. I can do it better myself.” This is a toxic mindset for a business owner to have. What I will tell you is it will hold you back from growth.

In my experience of working with thousands of coaches, of being in mastermind programs with other business owners, this is one of the main reasons why people don’t move forward in their business and why they are unable to grow their businesses to the level that they want and the reason why people are working too much and burning out. It’s important to delegate.
This can be tough because it’s your business. You want control. I get it. I’ve been there too. If you don’t learn to delegate, you will burn out. I can’t tell you how many entrepreneurs I’ve watched burn out simply because they are unable to delegate. It’s toxic. It can be the main reason why your business doesn’t grow.
In 2022, one of the biggest things I did was learn how to delegate better. I learned how to hire better and my business took off. I had a huge growth year in 2022, even though most businesses lost money. A big part of that was learning how to delegate and relinquish control. Something I do want to say is I am not a fan of a big team. I only want to grow to the point where I don’t need a massive team. There are some people out there who want that. They are into leadership. They want full-time employees. I don’t have a big team.
This might seem big to you because if you only have one person working for you or zero, this might seem big. Keep in mind that my business generates about $700,000 to $750,000 a year. I don’t have anyone who’s full-time. No one who works for me works full-time for me. No one is an employee. Everyone is a contractor and part-time.
The person who works the most for my business is my OBM Elise. She works about 8 to 10 hours a week for me. Sometimes, a little bit more. Sometimes, a little bit less. My virtual assistant, who mainly deals with our customer service inbox, works about 5 to 10 hours a week. I have a general VA, which probably does about 5 to 8 hours a week. I have a social media manager, my boyfriend, Ryan. He films my YouTube videos, scripts, schedules, and designs my social media content. I have a tech VA who probably does about 5 to 10 hours a month for me. She manages all the tech and sets up all the tech stuff in my business. I have four coaches who help me in my program. I have 3 experts in HTMA and I have 1 for HCA.
It’s not a huge amount of people. I know that you’re like, “That’s a lot of people.” I get it but consider where my business is at. I don’t think I’m going to hire much more. I will, at some point, hire a second coach for HCA and at some point, I will hire someone to help me in the DMs because I’m getting such a high volume of DMs. I can’t keep up. I’m going to have to hire that out. Other than that, I don’t think there’s anyone else I would need to hire.
The beauty of having my OBM, Elise, is she deals with the people. People rarely have questions for me because they’re always going to Elise. She manages the people and she makes sure the projects right are good to go. If we have a launch, she will figure out everything we need to do for the launch and she’ll delegate to me, which is great because she’ll give me a list of things I need to do.
The other thing that she does for me that I love, which is my favorite thing ever, is she creates a to-do list for me every week. Every week, I go into my Asana, which is a project management tool. I have a list in there and I have a bunch of check boxes. She’s like, “These are all the things that you need to do this week.” I love that.
The take home for this is if you are before the $80,000 mark and remember, these are loose. You should be outsourcing small jobs. At about the $80,000 mark, maybe a bit earlier. You can hire your first ongoing contractor. I recommend hiring an online business manager for a one-time project to come in and organize your business. You can hire an ongoing virtual assistant. I hope you enjoyed this episode. If you love this episode, I would appreciate it if you could give me a five-star review. You can go to RateThisPodcast.com/wealthy. I will see you next episode, where I help you become wealthy AF.
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