3 Key Steps to Hiring Success for Small Business Owners

If you are building your business mostly on your own, there comes a point where doing everything yourself stops being a strength and starts being the ceiling. Most small business owners hit that wall the same way: completely overwhelmed by the workload, unsure whether they need a contractor or an employee, and nervous about being responsible for someone else's paycheck.

In this episode of The Amanda Kaufman Show, HR consultant Kirsten Zeigler shares the proactive approach she uses with small business owners who are hiring for the first time. Her philosophy is refreshingly simple: treat people like people, get clear before you hire, and build the structure that lets your business actually grow. Here are the three key steps.

Step 1: Get Clear on the Role Before You Ever Post a Job

You cannot hire well for a role you have not defined. Getting specific about the work comes before you ever think about a person to do it.

• The Reason It Matters: When you bring someone in without a clear scope, you end up with one overloaded person wearing five hats and no way to measure whether the hire is working. Clarity up front is what makes everything after it easier.

• How to Do It: Kirsten's favorite starting point is a running list. Open a doc or a notes app and, over the course of a normal week, jot down everything you do, everything you wish someone was doing, and everything that keeps slipping through the cracks. Do not try to do it in one sitting, because you will never remember it all at once. Then categorize the list into buckets like operations and admin. The categories show you what kind of role you actually need, and they become the backbone of a real job description.

• Common Mistake: Trying to solve overwhelm by hiring one do-everything person. An executive assistant who runs your calendar, your social media strategy, your client fulfillment, and your operations is not an assistant anymore. Expecting one person to be a pro at all of it sets them up to fail before they even start.

Step 2: Contractor or Employee? Know When You Are Ready for a W-2 Hire

Contractors and employees are not interchangeable, and treating one like the other is where small businesses get into legal and financial trouble. The whole thing comes down to control.

• The Reason It Matters: The IRS and the Department of Labor classify workers using tests around behavioral, financial, and time control. The specifics shift with each administration, but the principle stays the same. Misclassifying a worker can turn into surprise legal bills and back pay you never budgeted for.

• How to Do It: Contractors are independent by design. They do defined, specialized work for a defined scope, often for a set period, and that is perfect when you are getting started. Employees are who you hire when your business needs to grow, not just maintain: people you can mold, rely on, and build around. If you need to control someone's hours, the software they use, whether they are on a company email, and how they speak to your customers, you are describing an employee. A good sign it is time for a W-2 hire is when you feel buried under general, ongoing work, not just one specialized project.

• Common Mistake: Calling an employee a contractor to avoid the cost and paperwork of payroll. Kirsten has seen owners face an EEOC complaint over something as avoidable as missed sick pay they did not know was mandatory in their state. Usually there is no ill will from the employee. They simply raise a hand, and the owner ends up paying far more in legal fees than the original obligation would ever have cost.

Step 3: Treat People Like People and Lead With Clarity From Day One

Most owners did not start their company to become a people manager. But the moment you hire a team, leading people becomes a real part of the job, whether you planned for it or not. This is where Kirsten's whole philosophy begins: people are not numbers, they are full human beings with their own experience, ideas, and personalities.

• The Reason It Matters: When you lead by assumption instead of communication, you start assuming a team member is not doing the work or does not know how. That creates anxiety, back-and-forth, and a slow erosion of trust on both sides. Proactive leadership prevents the spiral before it starts.

• How to Do It: Be proactive rather than reactive. Set clear communication and expectations before someone starts, and keep using the job description throughout their employment, not just during hiring, so both sides know what success looks like. Delegate and trust your team with room to be creative, while staying clear about the end goal. Put simple processes and regular check-ins in place so the relationship runs on communication, not guesswork.

• Common Mistake: Skipping check-ins and clear expectations because the honest conversation feels uncomfortable. It takes a little courage, but getting ahead of things with one clear conversation saves enormous time and stress later.

Stay Ahead of Compliance So It Never Bites You

Employment is a big commitment on both sides. The compliance details, like taxes, sick leave, handbooks, and classification, are easy to overlook until they become expensive.

• The Reason It Matters: There is no single reliable one-stop shop for current compliance information, and the rules change often. What you do not know can cost you, and the cost almost always lands at the worst possible moment.

• How to Do It: You do not have to become an HR expert overnight. Talk to an HR consultant or other owners who have made their first hire about where their breaking point was. Lean on good payroll and HRIS systems, which carry much of the compliance load and make sure taxes are withheld correctly. There are tools and people built to have your back through the process.

• Common Mistake: Assuming a quick Google search will give you accurate, up-to-date answers. A podcast or a blog is a great way to learn the right questions to ask, but it is not a substitute for advice from a pro.

Reframe the Fear: Why Your First Hire Frees You to Grow

Nearly every owner is nervous about their first hire, especially about being responsible for someone's pay. That fear is normal, and it is also a sign you are reaching an exciting milestone.

• The Reason It Matters: The fear can feel like a stop sign, but the owners who grow are the ones who treat the nerves as part of the milestone and make the leap with the right structure behind them.

• How to Do It: Reframe what the hire actually does for you. Even a role that is not tied directly to revenue, and your first hire usually is not a salesperson, frees up your time. When someone else handles the work that is below your pay grade, you get to focus on the bigger-picture, strategic, higher-value work that grows the business. Most states are at-will, so there is flexibility, and after the first hire, the second one comes with far more ease.

• Common Mistake: Staying stuck in the work you should not be doing because hiring feels risky. The real risk is capping your business at whatever one person can carry alone.

Conclusion

Hiring success is not about finding one superhuman who can do everything. It comes down to three steps: get clear on the role before you hire, choose the right relationship between contractor and employee, and lead the people you bring on like the full human beings they are. Do that, and your first hire stops feeling like a risk and starts feeling like the thing that finally lets you grow.

To hear the full conversation with Kirsten Zeigler, listen to Episode 330 of The Amanda Kaufman Show on YouTube, Apple Podcasts, or Spotify.

Frequently Asked Questions

When should a small business owner hire an employee instead of a contractor?

When your business needs to grow rather than just maintain, and when you are overwhelmed by general, ongoing work rather than a single specialized project. If you need to control someone's hours, tools, and how they represent your business, that points to an employee, not a contractor.

How do I figure out what role to hire for first?

Keep a running list for a week or two of everything you do, everything you wish someone was doing, and everything that keeps slipping through the cracks. Then group it into categories like operations and admin. The categories reveal the role you actually need.

What is the most common hiring mistake small business owners make?

Trying to hire one person to do everything. Expecting a single hire to be excellent at admin, operations, marketing, and fulfillment sets them up to fail, and it often leads to misclassification problems too.

I am nervous about being responsible for payroll. Is that normal?

Completely. Almost every first-time employer feels it. Good payroll and HRIS systems handle much of the compliance and tax burden, and the second hire is far easier once you have done it once.

Where can I get a free tool to help me start?

Kirsten offers a free job description template with built-in AI prompts so you can tailor it to your business and the exact role. DM her on Instagram at kdz_hrconsulting or connect on LinkedIn, or grab it directly at hi.kdzhrconsulting.com/freebie.

Transcript

Kirsten Zeigler (00:00)

it's really hard for a business to grow when you're just operating with a team of contractors. I do think that as you're starting to feel completely overwhelmed with the workload and it may be the generic workload, it's not like you need to bring someone in to work on a marketing project that's like super specific.

That's when you need to start thinking about hiring an actual W-2 payroll employee.

Amanda Kaufman (00:25)

hey, hey, welcome back to the Amanda Kaufman show. And we're going to have a great conversation today. I'm joined today by Kirsten Ziegler, who is a genius at HR. And she has a passion for helping the little guy, know, the small business owner. And I'm super excited to interview her slash pick her brain in front of you so that you will hopefully get some really, really juicy, awesome insights.

around your talent because guess what boo if you're building a business all on your own and you have zero plans zero roadmap for enrolling anybody to support you you just built yourself a job and so i think it's really important to to dig into all this here's and welcome to the show

Kirsten Zeigler (01:10)

Thank you so much for having me.

Amanda Kaufman (01:12)

Oh my gosh, and listener, I'm gonna just be super honest. Kirsten had me at her wallpaper. We were in a business incubator together, and I'm like, it's cool what you do, but I really like your wallpaper. And so that's pretty much what hit it off. But it wasn't very long before I realized, I'm like, oh man, I'm speaking to a bona fide genius in HR. So I'm super excited to have you here. Kirsten, if somebody was to just zoom away and you only got

one thing you wanted them to know about Great HR and their business owner. What's that one thing?

Kirsten Zeigler (01:47)

Man, I would say treat people like people. It sounds so easy.

Amanda Kaufman (01:52)

That's crazy talk. What do you mean by that?

Kirsten Zeigler (01:54)

Right?

People aren't just numbers, right? They're actual human beings. So just because you're hiring them to do a job, they're also full-fledged human beings that come with their own life experience and ideas and personality. And so, you know, that's like the bare bones of it. And obviously like you could peel that back like an onion to get to all the layers, but that's like bare bones. Treat people like people.

Amanda Kaufman (02:21)

Treat people like people. Easier said than done, I think. ⁓ a lot of business owners, I mean, they're cut from a different cloth. They think very differently. They have probably started their business being completely honest because they're a little bit of a black sheep in some way. So now they're enrolling people. So what are a couple of things that a very busy, high-stress business owner can do to treat people like people?

Kirsten Zeigler (02:23)

Totally.

Amanda Kaufman (02:49)

they really operationalize that.

Kirsten Zeigler (02:52)

So it's interesting because a lot of the times people, yes, like you're a business owner, you probably are a black sheep, but also you have a passion for something specific, right? So you created your business because you see like a gap in the market or you're super passionate about one thing, but that doesn't mean you've ever been a people leader before or a manager. You may not even be interested in that, but all of a sudden when you start to hire a team,

that becomes a big part of your job. And so I'm all about being proactive rather than reactive. A lot of HR is unfortunately reactive. So I like to work with clients on, how could we avoid bad situations from happening? And some of the ways to do that, and again, like these are all things that sound so simple, but in like the day-to-day reality, it gets complicated. So clear communication and expectations, number one.

So like before you're even hiring someone, sitting down and really figuring out what that person should be doing, what that job description should look like, and then using that throughout the person's employment as the basis for their role. Most people see job descriptions when they apply to a position. Use it during the onboarding process, too, because those are the expectations and then it becomes super clear. So there's no confusion for either side. Right.

Also, like, it's hard when you're a business owner to delegate. Like, we all know that. We want our hands in a bit of everything, right? So making sure you're able to delegate, that you're trusting your team, that you're allowing people some leverage, you know, and some ability to be creative and bring their own thoughts and opinions, but communicating what you expect as that end goal. And all of these things are ways that...

you can solve the frustration of a back and forth, right? And it saves so much time. It saves so much stress on both people's parts because I see when leaders don't communicate well, don't delegate well, don't put process in place, don't have check-ins with their team, it becomes more about assumption and...

That causes anxiety. That causes you to kind of like spiral a little, right? And you're assuming this person isn't doing anything or you're assuming they don't know how to do it instead of just getting ahead of it and having that conversation. So again, easier said than done all the time. I know it takes some...

Amanda Kaufman (05:17)

That's so good.

Kirsten Zeigler (05:20)

some courage sometimes, right? And, you know, a little bit of a knowledge on like how to talk to people and how to talk to even like specific team members and how your style of communication is. But I really do think just getting ahead of things is the best way to do it.

Amanda Kaufman (05:37)

Absolutely. And you know, you're reminding me of a couple of conversations that I had just in the past week with business owners who were just...

totally running as hard as they can and they believe and they're probably right that having talent is gonna be that thing that unlocks the next level of their growth of their business. And the thing that I kept hearing was I hired my executive assistant and then they had all these different roles that this person was playing. So like this is what I was hearing as a operator. I'm like, wait a second. So you've got somebody who's in charge of your calendar, in charge of your social media.

strategy in charge of fulfilling for your clients in charge of all of them

Like that's not an executive assistant anymore. So from where I'm sitting, I'm like, it seems like a lot of entrepreneurs are hesitant to have like talented, talented people that they have to pay and all of that. And there's also probably a bit of confusion about when's the right time to have an employee versus a contractor. Do you mind speaking to that a little bit, maybe shedding a little bit of a light to point to a business owner in the right direction there?

Kirsten Zeigler (06:24)

Yeah.

Absolutely. So this is something I talk about with businesses all of the time. The contractor versus employee conundrum, as I like to call it. so contractors, it's easy, right? When you're first getting started, you just need some help on some specific projects. It's a defined scope of work. It's a specific thing. So you're bringing in people to help you out who are contractors. I would say there are pros and cons to having contractors and employees.

It's time to start thinking about hiring employees when your business needs to grow, right? Like it's helpful to have contractors when you're kind of maintaining and building, but when your business starts to need to grow, you really need people there that you can mold, that you can rely on. Contractors are meant to be independent. That is like the whole gist of it.

And there are a bunch of like tests between the IRS and the Department of Labor if you want to get like super compliance driven. There are tests that determine whether someone's a contractor or an employee and those specifics of those tests.

They change every few years. It depends on like what administration is in place. But generally, the general gist of it is all the same. It's all about control, behavioral control, financial control, time control, the work, all control based. So in order to build a business and start growing your business, you need to be able to control somebody's work hours. You need to be able to control, you know, whether they're using a company email or not, like

what softwares they're using, how they're speaking to your customers, you know, like really also being able to set the tone for the work that they're doing. You can't do that with contractors. Contractors are there to do what they are skilled in doing, and usually that's for a short period of time, or you have a contract that you, you know, re-up or renegotiate based on the scope of work. So

You know, I do think that it's really hard for a business to grow when you're just operating with a team of contractors. I do think that as you're starting to feel completely overwhelmed with the workload and it may be the generic workload, it's not like you need to bring someone in to work on a marketing project that's like super specific.

That's when you need to start thinking about hiring an actual W-2 payroll employee. My favorite thing for people to do is just start a list. Like, open a doc, have a notes app open, something where as you're going through your day to day, you just start jotting things down that you're doing, that you wish somebody was doing, that you need to be done.

and you'll have a whole list of responsibilities after a while. Don't force yourself to sit down and do it in one sitting because you'll never remember everything you do, right? And then from there, start to categorize it. I like to categorize into like operations or like, you know, admin. And then you can kind of see what type of role you need. That example you gave about an EA doing a million different things, you're...

you're gonna end up in a compromising situation with that. You can't expect one person to be good at absolutely everything. And so you're already setting someone up for failure by expecting them to be a pro at all of those different things. It's really helpful, I think. know, admin, yeah, and EA does like go pick up.

stuff or you know like set meetings or run the calendar but that's still within a category of the type of work they do. ⁓ So

Amanda Kaufman (10:29)

Yeah, it's administrative,

it's executive functioning, right? And it's helping you as the executive to execute, right? So it's like an EA really is a more limited position. And I think like, yeah, I just see a lot of entrepreneurs, they don't want to pay the big bucks of having an employee in place. So they find funny ways of describing what the work is, but then

Kirsten Zeigler (10:34)

Yeah!

Amanda Kaufman (10:58)

you know, that really brings a bit of an opportunity for talent to take advantage of the business owner down the road if they discover like, wait, I actually have rights and I don't like this situation. And if there's a, especially if there's a conflict or something, you know, like that compliance stuff can feel like a pain in the butt, but boy, it hurts a lot worse if it bites you.

Kirsten Zeigler (11:21)

Totally, I've seen people get in trouble before with that stuff, like they just don't know, right? And so, and like maybe they have a great relationship with this employee and the employee may not have any ill will towards them. They may just be raising a hand to be like, you know, I had a client where they had a...

an EEOC case opened on them because somebody flagged that they weren't getting sick pay and they were in New York City where it's mandatory. And the business owner just didn't know. You know, if the employee had asked them, they would have said, no, I'm so sorry. Let's backtrack. Let's see how much you would have accrued. You can use it. But, you know, they flagged it and they paid so much money in legal fees trying to fight this. So, you know,

Amanda Kaufman (12:08)

Hmm.

Kirsten Zeigler (12:09)

It's unfortunate because there isn't a one-stop shop to finding all of this information that's accurate and up-to-date. Even doing a Google search, it's hard to find the most up-to-date compliance stuff.

Amanda Kaufman (12:23)

Absolutely. I mean, y'all, we're listening, you're listening to a podcast, right? So that's not the same as consulting an actual pro. But but it is useful. It is useful to just like say, hey, here's the questions I should I should definitely be asking. And, know, employment is a is a big commitment on both sides of the business and of the employee. You're talking about somebody giving their life force to your mission, you know, like it's a big deal. So like

What would your suggestion be to someone who is kind of thinking like they're ready to scale? Maybe they're nervous about having an employee because there's there's like tax implications. There's like you said, the sick leave, the having an employee handbook, like all these nitty gritty things that kind of add to it. And I want to just add one little thing. Entrepreneur, one of the reasons you're looking for somebody who is good at everything is because you think you are and you're not right. One of the big things that an employee

Kirsten Zeigler (13:05)

Mm-hmm.

Amanda Kaufman (13:20)

can absolutely do for you is be specialized in an area you have not had time to dedicate yourself towards. anyway, take it away, Kirsten. How can somebody get really good information about this?

Kirsten Zeigler (13:34)

Yeah, so I mean, first of all, speak with, ask questions, speak to an HR consultant or, you know, even other business owners, right, that are in your place to see what that breaking point was for them. I work with so many business owners who are hiring employees for the first time. And so really like, this is in my wheelhouse. They're usually scared about being responsible for somebody's pay.

Right with contractors you have a little more flexibility to end the engagement or you know not resign the contract with an employee where most states are at will. So yes you can let someone go at any time but there's a lot of things that they can come back with right to try to challenge that and so it is a little bit more of a process but

You can't do everything yourself, right? And so even if this person you're looking to hire is not a sales position, because sales is usually not the first role you hire, they're still going to be freeing up your time. So even though they're not directly tied to revenue, they are in a way, because your time, you'll have more time not doing the stuff that you shouldn't be doing. That's below your paid grade. Now you can focus on those bigger picture CEO.

strategic thinking, maybe bigger clients, right? Like you'll be able to bring in more money having that support there to take care of those like lower level tasks. So that number one, that is, you have to reframe it, right? Like if you're going to be nervous, that's okay. Every, I can promise you every single person is nervous, but it's also a really exciting milestone in your business. And after hiring the first person, you're gonna see

Okay, I can do this and then you'll hire the second person with so much more ease. And there are so many good payroll and HRIS systems out there. When I work with clients, I generally like to recommend which one's best for them, but that takes over a lot of the compliance piece when you're paying people and it makes sure that the taxes are being properly taken out. So there are definitely tools and resources you can use that have your back.

through this process.

Amanda Kaufman (15:49)

That's awesome. That's awesome. Kirsten, if people wanted to get to know you better, what's the best way to do that?

Kirsten Zeigler (15:55)

So follow me on Instagram, kdz underscore hr consulting, or find me on LinkedIn, Kirsten Ziegler. If you DM me, Amanda, I will send you a free job description template. It comes with some AI prompts so that you could really make it specific to your business, the role, but that is honestly the best place to start when you're thinking about expanding your team.

Amanda Kaufman (16:19)

super excited about that. think I may just slide into your DMs and snag that. Kirsten thank you so much for being here. We really appreciate this conversation.

Kirsten Zeigler (16:25)

Please, jail.

Thank you so much for having me. It was so much fun talking to you and I can talk HR all day. So I enjoyed myself.

Amanda Kaufman (16:37)

I love it. You light up. It's amazing. You

can really tell when somebody knows their craft and they get like really excited about it. Awesome. So, hey, dear listener, if you've got a friend or two or three who has considered hiring, is hiring, maybe has some regrets about hiring, make sure that you share this episode with them. I have a sneaking suspicion Kirsten may be back because we haven't had too many experts talk about this, but it's such an important part of business and growing your

talent. And yeah, don't forget to subscribe. If you haven't subscribed, like please just smash the button so you don't miss another episode. And by the way, if you have been loving the Amanda Kaufman show, one of the ways you can share the love is through a 30 second review. It helps new listeners decide whether they want to spend time with us. And of course, we really appreciate when you do. All right, my friend, we'll be back with another episode very, very soon. But until then, do what matters.