Top Five Hiring Mistakes Entrepreneurs Make

Jul 17, 2023

Hiring is a delicate process and I don’t really think there is just one right way to do it. What worked for one person may not work for you. After all, people are all different. But there are some common mistakes I’ve seen clients make–and I’ve made a few myself–that I’d like to help you avoid.

So I feel it’s worth a conversation on how to at least avoid the top five hiring mistakes entrepreneurs make. Whenever we can learn from the experiences of others, we become better equipped and more empowered. Speaking of which, I want to encourage you once again to check out my LEAD FOR WOMEN program. Through this program, myself and my team work with Elite Visionary Women who are effectively leading their teams to bring their genius to life… of which hiring is an integral part.

“The sooner you can sort of start to recognize there will always be a cadence to your business that will require you to be hiring, you can get, hopefully, out of this resentment, burden mode and just accept that this is part of what you do.” – Kris Plachy

What You’ll Learn

  • Bonus: Resenting it’s repetitive
    1. Taking fails personally
    2. Convincing candidate crushes
    3. Drying the pipeline
    4. Learning from waste
    5. Gifting invitations 

Contact Info and Recommended Resources

  • LEAD FOR WOMEN: Registration is open (currently there is a waitlist). LEAD FOR WOMEN is THE curated Leadership Development, Training AND Advisement program for Elite Visionary Women seeking to upgrade their skills leading, managing, communicating with, and inspiring the people you pay to achieve results in your business.
  • The Moxy Sage: Join with a paid subscription to hear more about this topic and others. Kris shares more in depth content every week and hosts a private podcast. 
  • Hawaii Retreat with Kris: September 22-25, 2023. A few spots are still available. This retreat is open to all women. See all the details and register at 
  • Get a FREE Month of Coaching on your Business Edit. Go to to access everything and learn more.

Connect with Kris Plachy


Hello, how are you? As we continue to open up registration for Lead for Women, I wanted to have a chat with you today about hiring. So let's do it.

So today I wanna talk to you about the biggest mistakes I see women, clients and myself honestly, make when we hire. And these may or may not resonate with all of you, but I do think it's worth a conversation. Because hiring is such a delicate process. There's just no, there's no way to do it perfectly. I am a firm believer that there are ways to be better at it than worse, but, doing it right, I don't know if that exists. I'm not sure if that makes you happy to hear me say that, but-

So let's just talk about what these top mistakes I hear in my clients, and have also maybe allegedly participated in myself over the years. So the first one is maybe less of a mistake and more of a belief, and that is that, "I should only have to do this once", or "I shouldn't have to fill this position again".

There is a running theme with most people, and that is that once I hire, I shouldn't have to do it again. And I've addressed this in other podcasts, probably most likely the one that I did on hiring PTSD. Where we just get worn down by hiring people and they don't turn out, they don't end up being the right people. They don't end up being the people we thought we hired. They don't end up wanting to work where they thought they were working. You know, it's just sort of a quagmire.

But what makes it worse is when we believe that we shouldn't have to do it again, that we should be able to find someone, hire them, and be done. It's a lie. It's a hope that makes you believe in a truth that I don't believe is real. I believe for as long as you lead and manage people, you will be hiring people, okay? And you will be firing people. And so the sooner you can start to recognize there will always be a cadence to your business that will require you to be hiring, you can get hopefully out of this resentment, burden mode and just accept that this is part of what you do.

The second mistake is that we take a poor hiring decision - meaning they don't work out - we take it personally. I've said this to so many clients and I think it's important to say again, and that is that you are your own beautiful person. And your business is an entity unto itself. Now, you obviously have a tremendous influence on your own business because it is of you, but as that business grows, it has to be less about you and more about the goals of the business and the reason that the business exists on the planet. Then we go out into the world and we hire people to fulfill roles in our business to ensure that the business delivers on its promise.

But what we do when we're entrepreneurs, and we're founders, we're business owners and even managers who've been in companies for a really long time, we start to over personalize what happens inside a business. And we define, especially when it comes to the people part, we define that very personally. And so when somebody doesn't work out, when they don't do their job, when they don't meet their goals, when they phone it in, when they quit, all the things, we get personally offended or insulted or hurt.

And I think that it's okay to allow yourself to have a day where you just sort of feel bad. But let's be honest here, this cannot be about you. Because if it keeps being about you, you're gonna be in the way. Your business needs you to be it's custodian. And if somebody doesn't work out, then you gotta get another one because the business needs the resource. You getting offended and hurt and then bringing that into the hiring process is not useful, and it can actually affect how you make decisions going forward. It can affect how you onboard people. There's all those pieces and parts.

The third mistake is probably one that will not surprise you, but it's that we miss red flags. We miss the telltales in an interview. But there's a real reason why. And the real reason why is that, as entrepreneurs, most of us started off building our businesses, which means most of us tend to have some sales competence. We're relatively good at selling. We had to be to start, right? So we get these people in our business that come in to get a job, and we can often fall into sales mode.

And that means that we forget that we're hiring somebody to come into our world, and to be scrutinizing and discerning about bringing a person into this business. And instead we invest too much time trying to convince or persuade or influence or highlight all the reasons why we're so great to work for. So all those skills that you used to attract a client and close a client are not the skills we wanna use to hire, okay?

Now, that doesn't mean you don't wanna put your best foot forward and you don't wanna present what the organization represents in a good way. But if you find yourself selling in an interview, then you are focusing on convincing this person they should work for you instead of exploring whether or not they really should. And just like we could get super excited about a potential customer or client, we get all jazzed about it, we can do that with recruits, with candidates.

I used to say all the time we would get candidate crushes and we would have these people that were like, "Oh, I hope they say yes. I hope they say yes." And a candidate crush is coming from an old energy of you wanting to close them. We don't wanna close the potential employees. I don't care how good the market is. You want to make sure you are absolutely discerning and bringing people into the business who need to be there, who are truly aligned to the values, who truly have the experience, who truly have the demonstrated results that you are gonna want in your business. It doesn't serve you to get too eager, okay?

Which leads me to mistake four. Mistake four is that we don't hire and interview regularly. So, I should actually say we don't interview regularly, so we can hire frequently. So let me rephrase that. The thing about hiring, if we go all the way back to the beginning, which is, "I don't think I should have to keep hiring. I should hire someone and that should be it", right? Okay. So we hold that mentality, which means we hire someone and then we stop thinking about hiring because we hate it so much.

Do you feel confronted? I'm sorry, is this feeling too real?

So you stop thinking about it cuz you hate it and then somebody leaves or someone has to get fired. So if it's somebody leaves, you don't have control over that. If you know someone's not performing, you keep them too long because you hate hiring. Well, keeping someone who's not performing because you hate hiring is a terrible idea. Not surprisingly, because it makes your business not perform to have somebody working in it who's not performing. Okay? But we go through that.

So what that ultimately means is we are not talking to people who might wanna come work for us, right? What we're doing is we're ignoring hiring. Just go sit in the corner. I don't wanna talk to you. But then we have a vacancy or a potential vacancy, and we have no pipeline. I want you to think about making money.

You know what? Money needs a pipeline. We've gotta be able to put money in the pipeline so that there's always money. We have to have people in the pipeline so there's always good people to hire. And no, you don't have to hire people just because you interview them. You can tell them, "Listen, I'm always interviewing and I'm always looking for exceptional talent. And meeting you today was really encouraging. I don't have an opening right now, but I'd love to stay in touch with you."

We nurture potential team members, nurture them. You never know what the future will hold, right? I've had clients who hired someone, but they kept the other candidates that were like, they're close second and they're close third, they kept nurturing them and then the first one doesn't work out. They've got their bench.

I can hear you. You're like, "Yeah, but it's so awful to interview. I don't wanna have to interview all the time." I understand. I hate washing my face and brushing my teeth, especially after I've fallen asleep on a couch. But you know what? I like having my teeth and I like a zit free face. So I do those things because I wanna look good and I don't want people to hate me because I have bad breath.

You have to be constantly interviewing. It comes with the job. You saying to me, "Oh, I don't like hiring. I don't wanna do it." It's like you saying, "Oh, I hate making money. It's just so exhausting to have to keep making money." That's what it sounds like to me. Because if your company can't thrive with people in the roles who are good at what they do, and you don't like hiring, that's what you're saying. "I don't like money."

Always be interviewing. Yes. Keep a posting out there. Yes, try new things. Even postings of people who have jobs. Tell them you do it. I always wanna meet people. Tell your staff, "Listen, you have a good person on deck who you think could work here. I'd love to meet them." If your company's big enough, maybe you don't do those. You don't do those initial interviews, but you have somebody who does. So the door is always moving, right? You've always got people.

Mistake number five. We think we wasted our time onboarding a potential new hire or onboarding a hire. We think we wasted our time if they don't work out. So you have not wasted your time if somebody doesn't work out early on in the onboarding. It is a hallelujah. I just had a client I talked to about this today. When people don't work out early, I'm always like, "Woo. Good one. That's good." it's good to know. You have not wasted your time.

Every time you put someone through your onboarding process, you learn more. This is why we have an onboarding process. Because people will show you who they are very quickly, and I want you to remember this flow. This is how my brain works. People will show you their very best self at the interview, okay? If they want a job, they are gonna show you their best version. That's it, right there. Whatever you got at the interview is the best version you're gonna get.

So if they're late, it's a no. If they show up on a Zoom call sitting on the floor with an unmade bed behind them and their hair's a hot mess, it's a no. No pride. No pride of appearance, of professionalism. No. It's a no. If you ask them to do a project and it's full of mistakes, no. If you ask them to do a project, then they turn it in late, no. This is their best version. It doesn't get better. It's not like, "Well, if I work with her for a couple weeks..." No, not while you're paying her. No.

Okay, so let's say they do show you their best version of themselves and they're, and that's a good version. And then they start. And then after week one, week two, you've got your onboarding plan. So you're holding them accountable. You've got some things that you want to see. How do they show up? How do they work with others? How do they follow through? If they start to not produce, perform, and behave in a way that you have already explained to them - because when you hire them, you explain your vision and your values and the expectations and the roles and all the things.

If in that first 30 days they're already late, they're already making tons of mistakes, they're already not achieving benchmarks, this doesn't make you happy. But it's actually good news. Because I'd rather know now. You do not need to take it upon yourself in the first 30 days of employment to turn someone into a another person. This is the best version of them, right? If the very best version was the interview, the second best is that first 30 days. You think that most people are trying to impress you. They're trying to prove value. They're trying to show you who they are, and if that's not happening, it's a no.

So you have to have a really clear onboarding plan or you can't hold them to that. It's very willy-nilly. You don't have anything to measure them against. You're sort of guessing. You're using your opinion. None of that is gonna help you substantiate if you don't wanna continue with the relationship. Okay?

And then the final mistake is that you treat a job offer as a gift to them of some sort. Like, "I'm gonna offer you this job. I'm gonna pay you this money, I'm gonna give you these benefits." Like somehow they're the winner. But what I want you to see, and so what that does is it changes the dynamic a little bit. It's like, "Well, we've selected you. We're very excited to have you." You make the relationship based on the role and what you're gonna give them. Instead of the invitation and agreement you're inviting them to.

And there's a difference because if it's all about what they're going to get, cuz they work for you, do you see how that tips the scale? But instead what we wanna do is say, "Hey, I'd like to invite you to come work here. Here's the role, here's the compensation and here's the invitation. These are the day-to-day responsibilities. This is the key result that I expect or that we expect for you while you work in this role. These are the key objectives and deliverables. This is the invitation. These are the expectations we have in terms of our values and how we want people to show up and interact with one another. Would you like to accept this invitation?"

Not, "Here, I'll give you this for coming to work for me." Do you feel the difference in that? And it's subtle, and maybe some people would say it's semantics, but I believe that leadership needs to be more aspirational than it is for most people.

We tend to focus on managing. I'm gonna do another podcast on this here because I think it's really important. We overfocus on the management part of what you do. We don't focus enough on the aspirational part of who you are and what you can invite people to. And I always want to speak to the highest version of somebody's self. And, "here's the invitation. Here's the potential. Here's how we're gonna be able to do this together. Here's why we are gonna do this as a team." Not, "If you come here, I'll give you this."

And, management feels very controlling. So that's why we like it. And especially as entrepreneurs who've founded and started the whole damn thing, you wanna stay in control. But what we really wanna do is invite this higher version of people to come and work with you, and realize a bigger potential of themselves than maybe even they thought was possible.

And that's all in the way you construct that initial invitation. Are you inviting them to join you and co-create in your company? Or are you hiring them and paying them an amount of money for a job? I think as small business owners, we have a lot of latitude in how we build these relationships with our team. And I would encourage you to reevaluate the way that you extend an offer.

So those are like the big highlights. There's also always a few more little pitfalls, and I'm sure you guys will have other things that you wish I had talked about. And if you have them, you can always email us at [email protected] and let us know.

You never know, I might do a part two based on your feedback. But I wanted to give you a little something because one of the vital assets, one of the vital asset skills that you need to have fundamental is hiring. You're always gonna be hiring someone. Even if you become the chairman of the board and you're running a $45 million business. You're gonna have to hire board directors. So you always have to be getting better at how you hire, and the best person to invest in to get better at hiring is you.

I know there's a lot of organizations that are like, "Use this instrument. Use this assessment. Take this test. Have them do this." I wanna help you become incredibly talented at reading people, at understanding what's going on in an interview and asking really good questions, at not getting sucked into the trap of selling instead of actually just asking and listening.

When you do that, it's a skill no one can take from you. You don't need an instrument or a test to tell you if somebody's a good candidate, cuz you'll trust yourself. Right? Isn't that ultimately what we want?

So we're open for registration for Lead right now. It's a wait list. If you go to, you can put your name on the wait list. We will be reopening actual registration acceptance here in the next several weeks. So I'd love to invite you to join us. It's an incredible program. It's all new information and content. It's an upleveled version of what I have done in the past, since I've been doing the work on Leadership Is Feminine.

You know, I'm really embracing the fact that we have a lot of power and authority as women and in our voice. But a lot of women don't understand and don't know how to tap into that. And that's not because they're weak, and that's not because men are the problem. It's because we've just had an imbalanced culture for so long that overly emphasized masculine approaches to things and underemphasize the importance of feminine approach.

And I want you to be able to be who you are and still feel strong and graceful and competent, and be kind and loving and also stern and firm and focused. So I think they can all go together. But I know you need tools, and I know you need support to do that.

So I hope you'll explore working with us if you haven't yet. Thanks for tuning in. And I'll talk to you again next time.

Lead for Women is now open for registration. If you're a woman and you are also a visionary, somebody who sees the world differently than it is, and you are eager to achieve that through your work and by leveraging the hearts and minds of others, then I invite you to go to thevisionary.CEO/lead and learn everything you can about our Lead program.

While it's not for everyone, it really is for you if you are a woman who is ready to learn how to think better, so you can lead better, and you can live better. You have a legacy to leave here and I wanna help you leave it by enhancing and improving how you show up as a woman who leads. Join us there.

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