Who to Hire in the Messy Middle of your Entrepreneur Journey

Aug 22, 2022

If you’re juggling the questions of “When should I hire?” or “Who should I hire?” – let me help guide you. The answers to those questions are completely tied to the answer to a question that should come first. That is, “What phase of growth is your business in?” This episode idea sprouted from help I’ve been giving to many regarding hiring and two recent Live Coaching with Kris episodes. As we navigate what I call the “Messy Middle” in building an entrepreneurial business, we need help but getting the right kind of help, at the right time, is absolutely crucial. If you hire the incorrect people during the a phase, you can actually lose touch and control of your own business. Please don’t let that happen. Let’s talk about who to hire in the messy middle of your entrepreneur journey.

“Learn how to manage. Anybody could work for you then. It’s fine. If you learn how to manage. But otherwise, you set yourself up where you don’t have control of so much of your business.” – Kris Plachy

What You’ll Learn

  • Phases and stages of business
  • Correct help in the Messy Middle
  • Correct help in the Established Phase
  • The quagmire of improper outsourcing
  • Hiring right at the right phase

Contact Info and Recommended Resources

Recommended previous episodes regarding hiring:

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Kris Plachy: It isn’t just about when should I hire? Or, who should I hire? But it’s also about what do I need right now in my business based on the phase of growth of my business, that determines exactly the answer to both of those questions? Let’s get started!

Welcome to Leadership is Feminine, I’m excited to talk with you today. I am doing this podcast actually sort of, it’s a little spontaneous, because it’s coming right out of the annals of several businesses that I’ve been supporting people in. And it just downloaded and occurred to me and I thought, I’m going to put this in a podcast, first of all, it helps me sort—verbal processor. So, it helps me sort out my thoughts, and I figured it would probably be useful for a lot of you as well.

So, here’s the thing, when you have a business, so let’s just let’s just walk through the phases and stages of most businesses. Now, founder/startup businesses can be different. And so and I don’t really do a lot of venture capital, I don’t work with a lot of those CEOs in my program, because a lot of those CEOs get C-suite teams when they get funding. So, a lot of private equity and venture capital firms will take a founder and their small business and then fill it up with people to support the growth of it. So, they sit in a different space. So, I really am talking to you, which is majority of you, that we call bootstrappers. You are the people who had an idea, proverbially started it in your garage or your back bedroom, and so on and so forth.

So, the first phase and stage of a business is really solopreneur. It’s you with an idea, doing the work, probably because it’s something that you were good at. And then you started to realize, “Oh, I can make money doing this,” then you started charging people, people love what you did, and then you decided to grow it. That’s how the majority of the women that I work with get started.

So, we have the Solopreneur phase when we are a Solopreneur and we get to the point where we can’t do everything in our business, then what we do is we get help. And I know you know what I’m talking about because that’s exactly how you say it, “I need some help. I need help. I need somebody to put things in boxes and send them. I need somebody to answer emails of my customer service. I need somebody to answer the phone. I need somebody to book appointments.” It’s very, very, “I need help.” And that’s perfect. That’s what you need is you need help.

So, in that phase of your business, that solopreneur startup phase, everything that we need to know about your business is in your brain. And so what you need is someone who can come in, take very specific direction from you and execute on what you need. And if they can do that, it starts to expand your capacity. So, if someone can ship your boxes, someone can answer your phone, someone can book your appointments. Now we’re changing your capacity, but everything resides in your brain. So, to use entrepreneurial management terms, you are the strategist, they are the tactician. You are the brain, they are the hands, and it’s perfect.

But then what happens is we get into this next phase. And this next phase to me is one we call… well, it’s been called lots of things, the messy middle, the messy Stage, I call it entrepreneurial phase. It’s this place where the business cannot exist on you alone. So, you have to start to hire more what I call players—these are people who do the same thing you do—to expand scope, reach and grow. So, in my world that’s hiring coaches and in someone else’s role that might be hiring other doctors, if you want doctor’s practice, other accountants, other lawyers, other florists, floral designers, other artists. Whatever it is that you do, you start to realize, “Oh, okay, now it’s not just me. I need help. I need people to do what I do.”

And the organization now starts to meet those five critical roles. Which is the clinic that we’ve just putting together that will actually be available to you soon. But we all need to have these critical roles as we grow our business. The challenge is that you are still driving the strategy. And that’s okay. Because you’re still close enough that you’re trying to figure out how am I making money? How do I get new clients? How do I increase engagement and sales and lead flow. All the parts that we have to start to do as our business grows. And most of us in this phase, do not have an established consistent client engagement attraction and selling strategy.

And I don’t care what it is that you do, you have to sell. Even if you’ve just decided, all you’re going to do is referrals, you still have to sell. So, there’s this hiccup that happens here. And this is where I see so many of my peers and my clients stuck. And I put myself squarely in this role. Because you need to be able to test frequently. When you don’t have a consistent strategy for onboarding clients, or attracting new clients or customers, you have to try new things a lot. We have to try several things sometimes at once. But what your brain wants, exhausted entrepreneur, is someone to come and do it for you. But the problem is, is by doing so you’re attracting strategists, you’re attracting people who want to build the strategy, they don’t do the work.

But you need somebody to do the work, right? So, we’re in this weird limbo. I don’t even know how many of the women that I know who are colleagues or clients who work particularly in the online space who have tried to find marketing support, who cannot find it. And the reason that they can’t find it is because we have either people who just know how to send out emails, or people who want to consult with you and help you build your strategy. But there’s nobody who will do both. And that, ultimately, is what we all need in this messy middle.

Because you have to have someone, some people on the team who can just get it done, and that it could change from Monday to Friday. But there’s so much log jam, at the strategic level that we’re attracting people who have all this knowledge, but they don’t roll up their sleeves. And I did a podcast some time ago, that I talked about why entrepreneurs need to be really, really careful when they hire corporate people, because corporate people—and I’m really generalizing. So, please forgive me that. But I hope you understand what I’m saying—corporate leaders, corporate people with a lot of corporate experience, are really, really used to having a tremendous amount of resources to deploy their ideas.

You don’t have that, you’re bootstrapping. So, you need to hire someone who can be creative and have ideas and be all in and dig into your business. And oh, by the way, also go in there and tweak stuff. And that is a very particular phase of your business. I’m calling it messy middle entrepreneurial phase, this when we go—I teach this in How to CEO—you go from you only, to we or just this “we group” and we’re trying to figure out how do we make this work with a bunch of people? Who does what? And where I see the most frustration for my clients is that there’s no phase in the middle. So, I really want you to understand that when you are deciding who to hire, you have to consider what stage and phase of your business you’re in.

If you’re a solopreneur just hire technicians. These are not people who are going to come and tell you what to do. Don’t ask them to. These are people who will just do what you ask. These are people who have experience in graphic design, bookkeeping, social media posts. And you just say, I want 12 of this to happen each week. Here’s the images, pull copy from here. Whatever it is. I want you to call this list of people and this is the script. We’re not looking for people to bring a robust strategy. And if you try and invite people at that phase to bring a robust strategy you end up losing touch with your business. So, please don’t do that.

This is stuff that I talk about with my clients all the time in How to CEO, which, by the way, registration is opening here soon. So, if you’ve been thinking about it, it’s time, it’s time to do this with me, we’re just beefing that up, it’s going to be amazing. We’re doing all sorts of really cool stuff. Plus, we’ve lowered the investment. I mean, come on, listen, I know inflation is hard on all of you right now. And I don’t want to contribute to that, I want you to get the support you need. So, come on, let’s go.

So, then we get into the Established Phase. This is when you’re sitting in that CEO role, the team is dialed, and things are really moving. This is when we hire what we call in the corporate world C-suite—this is when we start to hire our strategy deployers, our other leaders. But the only way we know we’re ready for that is we have a consistent producing business model. We are very confident that we have the systems in place, and the strategies in place that are making money. Do we continue to try new things? Always. We’re entrepreneurs. But we do not have to do that all the time, because we have a reliable system that drives success.

And so that is when you hire people who are the higher level, executive level, director and up people. Because those people will not generally roll up their sleeves and do the work, be producers, these are not tactician, and we don’t want them to be tacticians. We want them to be building out the strategy and then driving their team to do the work. And you, CEO, are being consulted with. “Hey, CEO, here’s our plan for first quarter to drive revenue, to collect our accounts receivable, to onboard new clients, to develop new products.”

Now that person is the ideator and they consult with you. That doesn’t mean you don’t still have ideas and you don’t get them done in your business. But I want you to feel that difference. Phase one, all you mama, all you and you just need help. “Hey, this is all working over here, just for me, can you help me with this?” Phase two is the messy middle. And this is when we’re in that phase and stage where we are trying to expand what we do but not just with us, it can’t just be me anymore. It could but it will limit my capacity, limits my ability to make money and limits my ability to serve whomever I’m serving.

But when we go through that phase, not only do I have to hire other players, but I have to hire people who willing to be in a test, it’s a startup test phase. And that requires expedience, quickness, flexibility, dynamic personalities. And we just talked to someone recently and asked like, well, what if we want to make changes to something? And the reply was, “Well, you can open up a ticket.” No, I don’t have capacity to wait to open up a ticket. That creates way too much lag in a small business. And I hope people who are listening to this are also people who support people like me, I really do hope you’re hearing me.

Because you also have to be clear about the client you want to support. And if you want it to be the kind of business owner that supports clients in the messy middle, then you have to be willing to be a tactician and a producer. You cannot sell to someone who is in the messy middle and be a strategist only, your partnership won’t last, unless you can deploy those services quickly. But in my experience, that doesn’t happen. I talked to the clients on the other end who are frustrated with this gap.

So, the first step is for each of you who are looking to hire is to be very honest with yourself and if you’re in the established phase, you’re running 3, 4, 5, $6 million dollars a year. You have a well-established team, you have well established systems and processes. You’re confident in most of the people that work for you and what you do to bring and clients, help the customers, whatever it is, and then sell to them again or move them along whatever your business model is. If that is operating very consistently, now we say, “Okay, I’m in the big girl arena now. And I’m going to get myself a C-suite. And I’m going to start to find other leaders who can uphold existing strategy and expand and develop what we already have.”

But if you’re in the place where so many clients are in that Messy Middle, and every month or quarter, or whatever, you’re like, “Oh, my God, how are we going to make this work?” you are not ready for just strategy, because you’re entirely too involved, which is fine. And you need tacticians, you need producers. So, working with someone like me, I don’t do the work for you. I don’t go in and write your job descriptions. I don’t go in and hire people for you. I’m not going to do that. But I will partner with you while you do that. And that’s absolutely fine. Because I want you to be managing your own resources. Because when you manage your own resources, you can take action.

I have some clients who come to me, and they’ve outsourced everything. They’ve outsourced their HR, they’ve outsourced their finance, they’ve outsourced their onboarding. I just talked to a client yesterday or the day before, she’s outsourced all her bills, she doesn’t manage anyone in billing, she has no control. So, she’s so frustrated, she wasn’t ready for that, she needs billing to work for her, because she’s got to be able to pull the lever. But the reason that you want to outsource is because you think it’s too hard to manage. But do you see the quagmire you set yourself up for when you do that.

Learn how to manage, anybody could work for you, then. It’s fine if you learn how to manage. But otherwise, you set yourself up where you don’t have control of so much of your business, and you think you’re doing something wrong, you’re not love, you just haven’t established who the best person is to hire for the stage and phase of your businesses.

And this, to me, is, if you figure this out, and it will change your life. Because once you can have authority over the day-to-day tactical work of people in your business, the faster you can move, but if you don’t know how to manage them, you’re going to lose your mind. And if you’re over hiring, so you’re trying to hire super competent, experienced people, they’re well beyond production, they’re well beyond tactics, you will be so frustrated because the work will get talked about, but the work will not get done. And also/or it won’t get done on the timeline that you need. And because you’re in the messy middle, you will find that you are going to change your mind a lot.

The business needs to be flexible, right now. You need to be able to test and try and do things, because you’re not established yet. And that’s okay. You don’t need to apologize for that. But you need to surround yourself with people who can do that and we’ll do that with you. What’s that saying? If you try and teach a fish to climb a tree, the fish will feel like a failure its whole life. That’s terrible. I’m sure I just made a mess out of that. But you know what I’m saying, right? And I think that’s where so many of my clients are sitting, at least when we first start working together is there’s all this shame, like somehow, I should be able to do this differently. But I have all these things I want to do. Yeah, you do have a lot of things you need to do because your business model isn’t established. You wouldn’t be doing that as much if you had a more established business model. So, we have to hire for phase.

Phase one, solopreneur. I need help, pure tactician. Phase two, messy middle entrepreneur phase. Got some strategy. I’m mostly leading it, but I need people who can deploy, deploy, deploy. I’m going to start hiring more experts, people who have a lot more competence in the particular area that I want to develop, but they’re still producers, they’re still tacticians, and they work with and for me. And phase three is when we start to look at that higher level leadership and they’re expanding on an established proven successful business model. I hope that all resonates for you.

And the podcast that I’m referring to is Episode 90. It’s titled, “Cautionary Tips When Hiring Employees from Corporate Cultures.” So, it’s not that people who work in corporate cultures are bad to hire. It’s just that I have witnessed repeatedly that when we hire too quickly at that strategic level, because we think we’re ready, we get a lot of conflict because those types of employees are typically not startup minded. They are not bootstrap minded. They are highly resourced minded. And so they’ll be looking for other people to do the work. But if you’re a team of six, you don’t have other people. So, hire for the right phase. And if you don’t know how, and you are uncomfortable with and you’re really struggling with managing people, let’s do this together, y’all. That should not be the reason that your business isn’t thriving, because that is solvable.

I’m imploring you, I just want to help so many of you thrive, your beautiful ideas. Do not let this part block that. So, you can go to www.krisplachy.com/howtoceo. All the information is there. We’re updating things as we speak. I would love, love, love to meet you, and work with you. Let’s get it, alright. Talk to you next time.

We have a lot of exciting changes coming up here at Kris Plachy Coaching Group, and I don’t want you to miss out. From leaving social media, to offering live interactions only to people on our email list. I want to make sure you don’t miss out. Head on over to www.krisplachy.com and drop your name and email in our little box there, and that way, you’ll get all the updates well before everybody else and even updates that nobody else will know about. See you there!

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