Hiring is often seen as a major milestone in business. It means you’re growing. It means you can finally get out of doing everything yourself. It means things should get easier. Except… that’s not what most business owners experience.
In this episode, Gwen and Tonya kick off their “What We Didn’t Know We Didn’t Know” series by unpacking the reality of hiring—why it’s both a blessing and a curse.
They explore:
- Why hiring doesn’t actually solve the problems most owners think it will
- What changes in your business the moment you bring someone on
- The hidden responsibilities that come with building a team
- Why things often feel harder after you hire, not easier
- What has to be in place for hiring to truly work
If you’ve ever thought, “Once I hire, things will finally feel manageable,”—this episode will give you a much clearer picture of what actually happens next.
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Watch the episode here
Listen to the podcast here
What We Didn’t Know We Didn’t Know – Hiring Isn’t The Fix You Think It Is
Over the years, Gwen and I have said some version of this more times than we can possibly count. Which is, you don’t know what you don’t know. If you don’t know what you don’t know, how do you figure out how to know it? The longer that you’re in business, the more you realize how true that is. For the next few episodes, we are going to pull back the curtain on some of the biggest things we didn’t know when we were building our business so that you can know it long before we did.
Now, most of these lessons have not come from a course we enrolled in, a book we read, or a podcast we listened to. Honestly, it wasn’t even that obvious to us until we were in the midst of it or all the way on the other side. These are the things that trip up even the smartest and most experienced business owners out there. Not that we think we’re the smartest, but we’re fairly smart. It’s not one of those things happening because you’re necessarily doing anything wrong.
It’s because nobody tells you what to look for. Maybe because they didn’t know it either. In this episode, we’re going to start with one that almost every business owner encounters at some point. This is one of Gwen’s. She didn’t know this. It’s hiring, because hiring feels like a turning point. It feels like you have leveled up in your business. It’s a sign that things are working but hiring changes the business in ways that you’re not always prepared for. That’s the thing we didn’t know, we didn’t know. Hiring is both a blessing and a curse. Gwen, why do you think most business owners believe hiring is going to fix all their problems?
Hiring Is Believed To Be A Silver Bullet To Fix All Problems
It’s one of the things that gets out there a lot of, “You need to outsource that so you have more time.” It’s the classic, “Hire a VA.” It’s the idea and it’s true when it’s done well, that you can clone yourself. You can multiply yourself. It’s like, “If I had someone else in the business, I could get so much more done,” which can be true. Part of the problem with this is, it’s not wrong. It’s just not completely right.
It’s not always right.
It’s not completely true. That’s why it’s so easy to get caught into this. We believe it’s going to be a bigger silver bullet than it necessarily is. We don’t realize the other side of the other piece of the equation. As I said, we all get caught into it because most of us, not all of us, start our careers as somebody else’s employee. We know how incredibly valuable we were to them.
I was good people, Gwen.
I did good work. I was super valuable to the people that I worked with. All of that was true and at the same point, it was not true. There are aspects about that I wasn’t seeing because I was on one side of the equation. There’s a point that’s also part of it is like, “It was so useful for my boss or whoever hired me for me, to be in the business. It’s going to be so useful for someone else for me to hire someone else to be in the business.” As I said, not that that’s not true because it can be true. It’s not just exclusively true.
Whether this is you or what you see with a lot of business owners. What do you think we expect to change once we bring somebody on compared to the reality that we face?
The Expectation Versus The Reality Of Employee Productivity
Most of us don’t remember how hard it was for us to get up to speed when we joined somebody else’s business. We didn’t have any view into our boss’s effort of getting us engaged. That’s the piece that is most missed. We have this belief that if we hire someone that they are going to hit the ground. They are going to immediately be super productive and it is going to immediately free up X amount of time. If it was taking us five hours a week to do a job and randomly picking something. That it will get that five hours back immediately.
We tend to believe that once we hire someone, they’ll hit the ground running, become instantly productive, and immediately free up our time. Share on XEven if we’re somewhat aware, it’s going to take a month or two before I get five hours back. We also believe that we will get all five hours back. That’s not true either, because there’s always some amount of management that has to be done by another person. Now, we may get four and a half hours back. We may get 4 hours and 45 minutes back at some point. We’re probably never getting all five hours back.
As you were talking, what flashed through my head are like three hiring experiences I had as an employee. First is probably what a lot of people face. It was the first job at the college and it was like you spend an hour with this person who’s doing the job we just hired you to do. I started working in a newspaper. I wasn’t the only reporter there.
You’re going to spend an hour talking to Ben over how he handles it and what the expectations are. This is after your HR paperwork part. You’re then going to spend an hour talking to an editor so you know what he expects then you’re on the job. Every learning you do from there on out is us correcting you on every mistake you make.
I was at that job for like eight years. My next job, I would say, was almost too far in the other direction but it was pretty cool. My entire first two weeks, Monday through Friday, 8:00 AM to 5:00 PM was scripted for me. My first day on the job, I was handed a packet that was like, “This is your itinerary for the next two weeks.” It started with going to HR and doing all the paperwork. They had everything down to my lunch break. You’re having lunch with Brenda. Brenda’s taking you out to lunch. You don’t have to worry about anything. We’re just going to take you out to lunch and during your lunch, here’s what you’re going to talk about. Brenda had been given an agenda to cover.
I have no doubt that Brenda had an agenda for this lunch conversation.
It was for two weeks. From that point, I had a weekly one-on-one for three months with my direct supervisor, then we went to monthly one-on-ones. After I hit the six-month part, then we went to as-needed one-on-ones. That was a little too far. I didn’t know that I needed every minute of my first two weeks’ schedule.
My third job was awesome. It was my first remote-only job working for a remote-first company. That consisted of, “Here’s a doc.” That doc was like an outline of, “We expect you to spend your first week doing this, your first month doing this, and your first three months doing this.” It had links. Things I was supposed to read, had videos I was supposed to watch, and meetings I was supposed to have. It was like, “Your first two hours of every day are on onboarding activities. The rest of your shift is spent doing the work.”
In all of those cases, you can see it took a lot of time to prepare to bring me on. Probably a lot of mistakes in hiring in the past. I was up to speed doing the work that I was hired to do in varying times. What I’m curious for you because in these examples, I wasn’t anybody’s first hire. What we’re talking about here is you’re making that first hire or maybe one of your first five hires. How have you seen hiring change your business, versus just supporting your business?
One of the biggest things is the communication piece. I’m in the process of developing slides for three things you can do to improve productivity for your employees for retailers, in this case. I’m going to an event where retailers are. The thing is, the facts are true whether it’s for retailers or for anybody else anytime that you have employees. The number one is communication. What we don’t think about with communication is communication done well takes time.
Communication done well takes time. Share on XIt takes time because it’s not only this part of talking but it’s thinking about what means to be communicated. Going through being reflective in that process and not just randomly spewing information from time to time. It’s being thoughtful about what needs to be communicated. It’s interesting with communication because everyone thinks they’re good at communication. We have communication experts, and some are better than others. You and I both come across those people. It’s like, “They are just always so clear. It always makes such sense.” Most of us think we’re way better than we are. Way better.
Communication Complexity Gets Exponentially Harder With More People
The other piece of it is when it’s two people, it’s a straight line. It’s two dots. I’m going to you and you’re going to me. Back and forth. That’s a fairly easy communication line. When there’s three of us, it becomes a triangle. There’s three points. I have two people to communicate with. You have two people to communicate to, and the third person has two people to communicate to. Still not too bad. As soon as we get to four, everyone goes, “Square.” Everyone knows what I’m doing here. I’m making shapes.
What we forget is there’s also lines through the center. It’s no longer just the outside lines. All of a sudden, we’ve gone from 3 lines in a triangle to 6 lines. We went from one line to just the two of us. We went to three lines when there were three of us. We went to six lines when it’s four of us. If you draw a line from every dot to every dot. When you make it five, I can’t do it in my head. I’d have to draw it out and count. It becomes way more than six.
There’s a lot of triangulation that can occur.
Very much. That’s the thing. Communication is more complicated even if the thing we’re communicating is not.
Is that the curse side of hiring?
That’s one of the curse side because we don’t often pay attention to that. We don’t understand that the communication gets exponentially more complicated as we add just one or two more people pretty early on. You start adding more and more. This is why big organizations have multiple layers of leadership because of that. That starts minimizing that to some degree. The other issue is people are people and people are complicated. They have free will. They have their own experiences that they’re bringing into the situation and their own emotional baggage, good and bad.
I say it all the time people are problematic. It’s the nature of being a people because we are. We’re fully independent. We’re free-willed. We’ve got all of these experiences and there’s no way I can give you enough of that information for you to be able to deal with all of that. They’ll be things that I might say or do that trigger you but would trigger nobody else. It’s not like I’m doing something HR worthy. It’s not that I’ve done something that’s obviously damaging but because of a prior relationship, a prior job, or a prior experience.
There would be no reason for you to say, “By the way, don’t ever say this because that will freak me out.” You’re not even aware of it. That’s one of the other reasons that the hiring piece is hard. It’s because, all of a sudden, something that was working stops working. It was because of some little tiny thing that you would never identify as the problem. You said something that got them in their head.
Now, they’re circling in their head like, “She’s going to find me any minute.” Even though that was not even on the plate in any way, shape or form. As the boss, I’m having to figure out how do I get you back into productivity. Back to that’s the people being a people. When I say people are problematic, I mean everybody because that also includes you, the boss person.
The same thing can happen in the opposite direction. Someone makes a little offhand comment. Not like in a Rudolph hand wage. You may not even know that you’re doing it. All of that ends up taking time. In some cases, unfortunately, we have people that appear to be good on the outside that are doing exceedingly damaging behaviors inside your business. If there’s not a way to catch it, you usually don’t catch it till there’s some serious damage.
There’s a lot of difficult aspects of hiring. Things that get harder after you hire people. You’ve touched on like communication is the big one. I think what else gets hired or gets harder after you hire people that you’re not prepared for it’s an aspect of communication. There’s the behavior piece but there’s also the fact that nobody reads your mind.
Especially when you’re in that like hiring the first three people to support you. I would say this is an area where, as an owner, I have unintentionally made things worse in my business after I hired somebody new. Though I know I have no right to expect somebody to read my mind. Subconsciously, I thought they would.
It’s not the you believe that. It just is so obvious to you.
Why would you not know this?
It’s so obvious that there’s no reason that you’d even think to communicate it. Back to people are problematic. You’ve got this experience, knowledge and history that makes that true. It’s not because you’re trying to be difficult. It’s like, “I’m going to show you that you don’t know as much as you think you do.”
A lot of times, as an employee, we feel like that’s what they’re doing. It’s like, “That’s not what they’re doing.” That answer is so obvious to them, they never even bother to tell you that piece of this particular equation. As I said, most of it is not done through any sort of malintent. We’re all just moving fast. Particularly as you said in those first 3 to 5 hires.
Do you think there’s anything else business owners assume that isn’t true? What I heard you say is we assume that what’s intuitive to us is intuitive to them. We assume communication is a lot easier than it is. We assume that everything we say is heard with the intent that we set it with. Fully ignoring the impact of our words based on intent that’s red that we may not know about. What else do we assume?
We assume that most people work under the same values and moral compass that we work under because it’s a harder thing to interview for. The people who are good at being able to interview for values usually have better hires. That’s a hard process and a longer process. A lot of times, we get very excited and we wait till the last minute then we hire to fill a spot.
People who know how to interview for values usually make better hires—but it’s a harder and longer process. Share on XSo long as you have the right skills, we bring you in. Often, the values piece does not show up until very late and out back to sometimes after there’s major concerns that come out. Anytime that we meet practically anybody, we assume that they have similar values that we do. Unless there’s key things that are obvious to say that they don’t.
Let’s bring some balance because we’ve talked a lot about the downside. When do you think or when have you found hiring is the blessing that the business owner hopes it would be?
When Hiring Becomes A Blessing For The Business Owner
It is a blessing when someone comes in and is able to get up to speed and do the thing that you need to have done. My example earlier was like, if this is taking you five hours a week, you’re not going to get five hours back. You might be able to get four and a half hours back or 4 hours and 45 minutes. That’s a blessing piece. What’s even a bigger blessing which can happen when you start hiring people who are better than you are.
What was taking you five hours only takes them two hours. Not only did you get your time back. It’s probably costing you less than it would have to replace you in the legitimate sense because it’s taking less time and/or if they’re coming in as an employee. There are so many more things that they can do. Even if you’re only hiring for five hours a week. You’re getting out an equivalent of ten hours of work, of your work because it takes you so long. That used to be one of the things.
For me, one of the VAs that I worked with years ago was fast at writing. She had a master’s degree in English and in Library Sciences. She loved writing and I didn’t care. It’s not ever been my big thing that writing had to be just so. I just wanted it to communicate the piece. I could spend 30 minutes with her brainstorming ideas. She would come back with less than two hours of work with 3 or 4 articles.
Now, someone like you that’s very concerned about how it’s written may not be happy with those articles but they were fine for me. To get that same level of article out would have taken me 4 to 10 hours. It’s a huge win. That does happen. The other along the same line is when you hire someone who’s better than you at the thing that they start doing the thing better or they make improvements on it. They may bring new insight into the process so that you’re able to make further progress than you would have if you had kept it all under you and your responsibility.
That’s a place where hiring makes a lot of sense. The other place I find is a lot of times hiring helps clarify things for yourself. Especially when we’re talking about those first, like 3 to 5 hires. Not as true if you’re in a larger organization as you said. Your early examples were, “I’ve been at this organization.” Obviously, this was a well-established organization because they had thought it through.
One of the other things that hiring can be super valuable for is getting clear on what you’re not clear on. All of a sudden, it’s like, “This felt like this is super easy but I see it’s complex. Maybe we do need to simplify it.” Those are some right off top of my head. I bet you have some, too. Are there things that strike you that I haven’t brought up yet? You’ve been on both sides of this equation yourself.
I’m going to tell you. This has been a blessing for me. I don’t know that another business owner would consider it a blessing. The blessing for me of hiring people has been to force me to confront how disorganized I have been in things and how much I have flown by the seat of my pants. What I would ask you is the follow-up question if you had just asked me that. What has to be in place for these blessings to happen?
What you have to have in place is some system and some structure to the system. I’m not going to say you have to have SOPs because everybody has a standard operating procedure. You’re the one who pointed this out to me. Many of us just don’t have them down. I do think that in order to truly experience the blessings, you have to have some stuff written out in order for the person to be self-sufficient.
Nobody can just parachute into your organization and know how you would do things if there’s not a place for them to refer to whether it’s a handbook, a manual, or some videos to watch. I think the more structure you have with your business, the more that you have written down and documented in some fashion. The better able person is to alleviate the pressure that you’re facing.
Going back to your part about values because I agree with you. I never would have said that, but that’s 100% true. If all you have written down is your mission, vision, and values. It’s like, “These are the values that we employ, with how we deal with clients, and how we deal with customers. Even that will make them more self-sufficient right off the bat.
To be clear, when we say mission, vision, and values, we’re not talking about the one that’s been WordSmith that needs to be on the poster at Coca-Cola. It can be rambling. It can be whatever it needs to be so that you feel like it conveys the information. A lot of times, people say, “I don’t have a mission statement.” It’s because mission statements in the way that we’ve been trained to think about, especially when we’ve been an employee in a bigger company, are stupid. They’re created by committees and wordsmiths.
When we talk about mission, vision, and values, we’re not talking about polished corporate slogans. They can be messy or rambling—whatever best communicates who you are and what you stand for. Share on XFor you, what would you say mission or vision or whatever? If I was to say, “What’s your mission? What are we doing here?”
My mission is to help women entrepreneurs focus on how they can be moving the needle forward in a way that’s totally an alignment with them and what their real goals are. Not what they think society’s goals are. To do it in a way that is sustainable for as long as it is appropriate.
For me, I would synthesize my mind simply to be like online platforms should be used to bring people closer together and not drive them further apart.
For the purpose of what we’re talking about. In either case, someone coming in or organizations would say, “I get an idea of what you’re doing.”
Let’s land the plane, so to speak. If you could go back, Gwen, and tell yourself one thing before you hired your first person. What would it be?
I have two things and maybe three.
Go for it.
Essential Advice: Trust But Verify, Hire Slow, And Fire Fast
The first would be, don’t assume people are good just because someone says they’re good. This is that whole value of alignment and where I often use the phrase trust but verify. That looks like a lot of things. Sometimes, it’s about behavior or doing the work. There could be lots of places. The second thing that I would say is be cautious in hiring family and friends. Most of the time, that’s going to backfire on you at some point in time. It’s hard to separate those two relationships. They need to be in a different relationship. There’s a different relationship between being a friend or a family member than there is of being a co-worker. Particularly, a boss and an employee.
That was another early-ish on mistake. This is going around quite a bit now, but I support it 100%. The third would be to hire slow. When you’re hiring slow, you’re focusing on behaviors and attitudes because you can’t train that. You can train skills and fire fast. There has never once been a situation where I say to myself, “It would have been better to keep that person for another month.”
It’s also true for every client I’ve ever coached, they have someone leave. A month later, it’s like, “Are you disappointed that they’re not here for another month?” No matter what they thought the outcome was going to be and what all of the disaster that was going to happen by letting them go. No one has ever said, “I made a mistake letting them go too early.” Never. Almost always. “I should have done that 3 months ago or 6 months ago or a year and a half ago, had that one time.” That whole hire slow, focus on that behavior and attitude piece and fire fast. Those would be the three.
I wanted to add stuff but I have nothing to add to that. Those are good ones.
Sorry. I took it away.
Those are the three biggies. I 100% agree. Here’s what I’m going to say. Ultimately, to close out the episode. Like any other aspect of your business, there is no one-size-fits-all solution. Hiring isn’t going to instantly make your business better any more than getting married makes dating relationships any better.
It kind of does because now you don’t have to date anymore.
That is true. Dating sucks.
It doesn’t make your relationship with that person any different.
It doesn’t. It is going to shine a bright light on the weak points and it is going to enhance the strong points. It’s still going to be what it was. Whatever you can do to strengthen your business before you bring on somebody else, do it. It’ll make your hiring experience so much better. If this episode resonated with you, you should be subscribing to One Good Question.
One Good Question sometimes is all it takes to break you through the bottleneck that has been spinning around and around for you. You can subscribe to Gwen’s Good Question email, which drops in your inbox every single Friday at EverydayAffectiveness.com/Question. We will see you next time where we are going to talk about the number one thing I wish I knew earlier in my business than I did.
Mentioned in This Episode
About Your Hosts
Gwen Bortner has spent four decades advising executives and entrepreneurs in 45+ industries. She helps women succeed in business without sacrificing happiness by identifying their true desires and aligning their business functions. She spots overlooked bottlenecks and crafts efficient plans toward sustainable success that center your values and priorities. Known for her unique approach to problem-solving and accountability through the G.E.A.R.S. framework, Gwen empowers clients to achieve their definition of success without sacrificing what matters most.
Tonya Kubo is a marketing strategist and community builder who helps entrepreneurs build thriving online communities. As co-host of The Business You Really Want and Chief Marketing and Operations Officer (CMOO) at Everyday Effectiveness, she keeps conversations on track and ensures complex business concepts are accessible to everyone. A master facilitator with 18+ years of experience in online community building, Tonya takes a people-first approach to marketing and centers the human experience in all she does.
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