When you run a small business, there comes a moment when you feel the pull to hire — that whisper that maybe it’s time to bring someone else on board. I felt it myself not too long ago. In one of my Visionary Vibes newsletters, I admitted I wasn’t totally sure what direction I wanted the newsletter to take, partly because my business looks radically different than it did a few months ago (and wildly different than it did a year ago). In that email, I casually mentioned that everything was growing so fast I could probably stand to hire. And let me tell you, that one throwaway line about hiring small business team members got a bigger reaction than almost anything else I’ve written.
The replies flooded in — nearly 30 of them. And one in particular stuck with me. A reader (we’ll call her Kara) wasn’t sure if she should hire for her brick-and-mortar business. She worried about whether sales would slow down, whether she could afford it, and whether she could even manage all the paperwork. All of those doubts are real, valid, and common. But they’re also the exact kinds of questions you should be asking if you’re considering hiring in your small business. That’s why I decided to turn her question into what I’m calling a “masterclass” — a deep dive into how to think about hiring for small business growth in a way that feels intentional, safe, and strategic.
What’s inside this episode:
- The simple litmus test that tells you what your first (or next) hire should be able to do — and how to spot that thing before you post a job
- The “90-day runway” rule that keeps you from white-knuckling payroll — plus when to bump that to six months
- When SOPs are non-negotiable (even for tiny teams) and how to have your hire draft them while you train—without lowering standards
- How to sneakily get some extra bang-for-your-buck out of your next hire
- A tiny distinction between two types of hires that explains 90% of onboarding headaches
- A lesson I had to learn the hard way about choosing between “potential” and “ready right now”
- The permission slip you need to stop waiting for “every duck in a row” and start making smart, data-backed calls with your gut
Why I Haven’t Hired Yet (And What I Consider First)
Here’s the thing about hiring in a small business: it’s rarely as simple as “I need help, so I’ll bring someone on.” The impulse can be strong — I felt it myself, that urgent desire to add one or two more people to my team. But I held back, and here’s why.
The first issue was time. I knew that if I brought someone on, I wouldn’t be able to properly train them. I didn’t yet have the standard operating procedures (SOPs) in place for the roles I wanted to hire for, and without those, it would be unfair to expect a new team member to succeed. If you’re hiring contractors or service providers, they should already come to the table with the skills you need. But for an in-house team? You owe them training, structure, and systems.
The second issue was financial.
I’ve created a rule for myself that I won’t add payroll expenses unless I have 90 days of operating runway saved in liquid cash. That means enough to cover payroll (including my own paycheck) and all expenses for three months, no matter what. And if I were about to take on a particularly big expense? I’d bump that up to 180 days. Why? Because I’ve lived through the stress of wondering how I was going to make payroll, and it’s not a situation I ever want to repeat.
Even though I tend to be very risk-tolerant in other areas of business, I refuse to gamble with other people’s livelihoods.
So before you think about hiring small business employees or contractors, ask yourself:
- Do I have the time and systems to train them properly?
- Do I have at least 90 days of operating expenses in cash reserves?
- Am I truly ready to take responsibility for someone else’s paycheck?
These questions aren’t meant to scare you — they’re meant to set you up for success. Because the truth is, being conservative on the front end often saves you heartache (and money) down the road.
Kara’s Question: To Hire or Not to Hire?
When I sent that email about hiring, one reply stood out. A reader — we’ll call her Kara — wrote in with a question that so many business owners wrestle with when it comes to hiring for your small business. Her hesitation and fears will sound familiar to just about anyone who’s been in her shoes.
She said:
Honestly, it is just a gamble on myself. Or at least that is how it feels to me. I need to be open on Saturdays, but I cannot physically be at work on Saturdays because we have four kids at home. I can afford to hire someone for one day a week, and it would bring more opportunities for me to make more money, thus I could have them work more than one day. It is a snowball effect, but being so new, and it going into the colder months, I am nervous to move forward on it. There are so many what-ifs. What if sales slow down through the cold months, and I can’t afford to keep the person I hired? What if the person I hire doesn’t work out? How do I do all the paperwork involved with hiring someone? What bases need to be covered? There is just so much that goes into it.
Here’s the thing: everything she listed is completely normal. In fact, the very act of thinking through those questions shows a level of intentionality that makes her more ready to hire than she realizes. The business owners who blindly rush into hiring without considering runway, systems, and the “what ifs” are usually the ones who get burned.
So if you’re in Kara’s shoes — weighing whether hiring for your small business is the right next move — it’s smart for you to be thinking about those things.
But let’s get into more of what you can be thinking about.
1. Revenue-Generating Hires
When you’re hiring for small business growth, the very first question you should ask is: will this person pay for themselves?
Too often, owners make their first hire to “take things off their plate.” That might feel like relief in the short term, but it’s not sustainable unless that hire is actively supporting revenue. Your first team member — whether they’re behind the counter, answering calls, or running the register — should create more opportunities for money to flow into the business than they cost to employ.
In Kara’s case, Saturdays were the clear opportunity.
Right now, she can’t open on Saturdays because of family commitments, but she also knows that’s one of the busiest shopping days of the week. Hiring someone for even a single Saturday shift isn’t just about covering the store — it’s about unlocking a whole new revenue stream. Every sale made that day is money she’s currently leaving on the table.
Here’s how to think about it more concretely.
Let’s say she wants to hire someone at $15 an hour. Once you factor in taxes and other employer costs, the real hourly cost is closer to $18.75. If that person works a seven-hour Saturday shift (to cover opening, closing, and everything in between), the total cost is about $131.25.
That means Kara’s store has to generate at least $131.25 in profit just to break even on that one day.
Now, here’s where most small business owners get tripped up: you don’t just look at gross sales, you look at profit. If you’re doubling wholesale costs — say you sell an item for $20 that cost you $10 to stock — then the store needs to sell $262.50 in retail sales to cover that $131.25 payroll cost. Everything after that is additional profit. And if Saturdays really are strong shopping days, hitting that number may be more than realistic.
This is what I mean when I say your first hire should be revenue-generating.
It doesn’t necessarily mean they’re out there selling aggressively, but it does mean their role directly contributes to sales happening that wouldn’t otherwise exist.
A body behind the counter on a day you’d otherwise be closed is revenue-generating. An assistant who frees you up to book three extra client calls a week is revenue-generating. A contractor who runs ads that bring in customers you couldn’t reach alone is revenue-generating.
When you frame hiring for your small business this way, it takes the fear out of it. Rather than thinking about it just as adding overhead — you can feel more confident that you’re investing in growth.
The math shows you exactly what has to happen for that hire to make sense. And when you can tie their hours or projects directly to revenue, you give yourself the confidence to move forward knowing you’re not gambling, you’re making a calculated move.
2. Hiring for Replication vs. Innovation
When you’re hiring for your small business, the next critical question is: am I hiring this person to replicate or to innovate?
Those are two very different types of hires, and confusing the two is one of the biggest mistakes business owners make.
Replication means you already know how something should be done. You’ve done it yourself successfully, you’ve proven the process works, and now you just need someone else to carry it out.
Innovation, on the other hand, means you don’t yet know the best way forward. You’re bringing someone in not just to execute, but to design the strategy itself — to create the process where none exists.
Why This Matters in Hiring for Small Business
If you’re hiring someone to replicate, you owe them tools and training. That usually means building SOPs (standard operating procedures).
These don’t need to be complicated; they can be simple checklists or step-by-step instructions that remove guesswork. When I ran a theatre, I had checklists for stage managers: what to do before rehearsal, what to do after, what needed to be checked off every single night. It wasn’t fancy, but it eliminated excuses. Everyone knew the standard, and if it wasn’t done, I could point to the checklist and say, “it’s right there.”
This is exactly how you set a new hire up for success in your small business.
Whether it’s running the register, opening and closing the shop, or managing an inbox, documenting the “how” makes it repeatable. And when you have SOPs, you’re no longer relying on someone’s memory or interpretation. You’re setting the standard in black and white.
But… if you’re hiring for innovation, the dynamic shifts.
You’re essentially saying: “I don’t know how to make this work, but I’m trusting you to figure it out.”
That kind of hire requires a much higher skill set, and it costs more. You’re not just paying for execution, you’re paying for expertise, strategy, and problem-solving. Think of hiring a marketing strategist to design your ad campaigns from scratch, versus hiring a junior marketer to schedule posts and send emails. Both are valuable — but one comes with a very different price tag.
Kara’s Scenario
Looking at Kara’s situation, I can be fairly certain her hire would be replication, not innovation.
She already knows how to run her store. She already understands how the register works, how to open and close, how to serve customers. She doesn’t need someone to reinvent retail strategy; she just needs someone to be her on Saturdays. That’s a replication hire — and that’s good news, because replication hires are easier, cheaper, and safer to onboard when you’re just beginning to build a team.
One more note: you don’t always have to write every SOP in advance.
Sometimes the best way is to document as you go. Train the person hands-on, then have them write up the steps they followed. Often, fresh eyes catch the details you take for granted. For example, I’ve seen people leave out “check the alarm before leaving” because it’s second nature to them, but a brand new employee wouldn’t think of it. By letting them write or refine the SOP, you create a tool that’s both accurate and usable.
3. Using Data to Inform Hiring Decisions
Numbers don’t lie, and when you’re hiring for small business growth, data is your best safety net. Too many entrepreneurs make hires based on gut feelings alone — “I feel busy, so I must need help.” But if you can ground that decision in real information, you’ll feel far more confident about taking the leap.
This is the process I’d look at:
Step 1: Look at Your Own Historical Data
Start with what you already know. How much revenue does your business generate on a typical day? What’s your average ticket size? How many customers come through the door (or book calls, or buy online) in a given week? This gives you a baseline for projecting whether an additional team member is worth the investment.
In Kara’s case, she doesn’t have Saturday data because the store isn’t currently open then. But she can still look at weekday numbers. If Mondays through Fridays bring in steady revenue, there’s a good chance Saturdays — a prime shopping day — will perform even better. Even without Saturday-specific history, her weekday data provides a benchmark.
Step 2: Borrow from Competitors and Industry Patterns
If your own data is thin, borrow from what’s publicly available. Google Maps, for example, shows foot traffic patterns for almost any business with a profile. Search for similar businesses in your area and check their “popular times” graph. You’ll see which days (and even which hours) tend to be busiest.
If you’re a coffee shop, look at other cafés within a mile or two. If you’re a boutique selling home goods, expand your search radius to five miles and check out other retailers. Even if they’re not exactly like you, their traffic patterns can give you useful clues. Saturdays usually spike compared to weekdays in most retail operations, which means keeping your doors shut that day is leaving money on the table.
Step 3: Translate Data for Hiring Confidence
Once you’ve gathered this information, run the numbers against the cost of the hire. If you know an employee costs you $131.25 per Saturday (like we calculated earlier), compare that to your daily sales average. Does your weekday revenue suggest you’d easily exceed $262.50 in sales on a Saturday? Does competitor data back that up? If so, that’s a data-driven green light.
And if your gut is saying, “I’m not sure Saturdays would perform the same way”? That’s valuable too. Sometimes your instincts highlight factors data can’t capture — maybe your location doesn’t get weekend foot traffic, or your product is seasonal. In those cases, you can test small (start with one month of Saturdays and track results) before fully committing.
Using data grounds the decision.
It shifts hiring from “what if I can’t afford it?” to “what revenue would this hire need to generate, and is that realistic?” That clarity is important. Instead of gambling, you’re running an experiment with a clear hypothesis and measurable benchmarks.
Hiring for your small business will always carry some risk. But when you back your decision with numbers — both your own and industry data — you’re going to move forward in a more intentional, grounded way.
4. Creative Solutions — When Your Hire Can Do Double Duty
One of the best ways to reduce the fear around hiring for your small business is to design the role so it serves more than one purpose. In other words, how can you make the hire do double duty?
This isn’t about piling on unrelated tasks or overloading someone. It’s about thinking strategically: if business is slower than expected in one area, how else can this person add value so they’re still paying for themselves?
What Else Could Your New Hire Do (Ideally to Help You Make Money)?
In Kara’s situation, Saturdays may or may not be consistently busy. Some weekends could be packed, others could be quieter. That unpredictability is what makes her nervous. But what if she hired a younger employee who could both staff the store and help with… let’s say, marketing?
Imagine a college student or even a responsible high school senior who not only runs the register on Saturdays but also films TikToks, updates Instagram, or creates behind-the-scenes content while on shift. Worst-case scenario, if foot traffic is slow, they’re still using their time to build brand awareness and attract future customers. Best case? They’re both covering the store and drawing in more business. Either way, they’re revenue-generating.
This kind of approach blends the two hiring categories we talked about earlier — replication and innovation. Most of their job is replication: following SOPs, opening and closing properly, serving customers.
But the secondary role gives them a bit of innovation: using their fresh perspective and digital fluency to connect with peers and drive visibility.
This works in other industries too.
A VA who handles your inbox could also draft simple social posts. A project manager who organizes client deliverables might also track KPIs and flag trends. You don’t need them to master a second specialty — just contribute in a way that stretches their value beyond the core function.
And if you’re like, “oooh I love this for me” (same), I’d encourage you to build the job description as such, so you’re intentionally hiring someone who would be excited to take this on. But you could always just add it into the job application, eg asking a question around, in this case, social media content… and then bring it up at the interview!
Why Double Duty Works in Small Business Hiring
Small businesses don’t always have the luxury of hiring single-focus roles. Every payroll dollar has to stretch.
By intentionally designing roles that combine a core responsibility with a secondary contribution, you reduce your risk. Even if sales dip or demand fluctuates, that person is still helping the business grow in another way.
And just as importantly, this gives you breathing room. Instead of stressing over whether one slow Saturday will “justify” payroll, you can see the hire as an investment in both operations and marketing. That shift in mindset makes the decision feel less like a gamble and more like a strategic move.
Rapid-Fire Answers to Common Hiring Fears
Every small business owner goes through the same mental checklist of fears before making their first hire. Kara spelled them out perfectly, so let’s tackle them head-on.
What if sales slow down?
This is always a possibility, especially with seasonal businesses. That’s why I stick to my rule of keeping at least 90 days of operating expenses in cash. If revenue dips, that buffer allows you to keep paying your team without panic. And if you discover, for example, that winter months just don’t justify weekend hours? You’ll know better next year and can adjust staffing accordingly.
What if the person doesn’t work out?
Here’s the hard truth: eventually, it will happen. Not every hire will be a perfect fit. Your job is to minimize the risk by giving them SOPs, clear expectations, and proper training. Beyond that, remember this: you can teach skill, but you cannot teach personality. If someone isn’t a fit with your customers or your team, it’s better to know early and move on.
What if I hire the wrong type of person?
Don’t fall into the trap of hiring based on potential. Small business owners are visionaries — we see what someone could become. But your first hires need to do the job well right now. Potential doesn’t pay the bills; proficiency does.
What about the paperwork?
This feels scarier than it is. Payroll services like Square and Gusto walk you through every step. They make sure you’re set up for taxes, compliance, and reporting. You can’t even run payroll in Square until you’ve completed everything required — so it’s basically foolproof.
How do I cover all my bases?
Here’s the truth: you won’t. Hiring for your small business is never about having every duck in a row. If you wait until you feel 100% “ready,” you’ll never hire. Instead, focus on having your financial buffer in place, your SOPs drafted (or in progress), and your gut saying, “yes, this makes sense.” Beyond that, it’s about adjusting as you go.
To Wrap it Up: Hiring for a Small Business with Confidence
Hiring for your small business will never feel like a zero-risk decision. There will always be “what ifs” — what if sales slow down, what if the hire doesn’t work out, what if you missed some paperwork? But as you’ve seen, those questions don’t have to stop you. They’re actually the signs that you’re thinking like a responsible leader.
When you approach hiring with the right framework — asking whether the role is revenue-generating, clarifying whether it’s replication or innovation, grounding your decision in real data, running the numbers honestly, and getting creative about stretching the value of the hire — you transform hiring from a gamble into a calculated, strategic move.
Will every hire be perfect? No. Will turnover happen eventually? Yes.
But the more intentional you are about when and how you bring people on, the more you protect both your business and your peace of mind. You’re not just filling a role — you’re setting the foundation for sustainable growth.
And remember: you’ll never have every duck in a row. At some point, it comes down to a gut check. You’ve done the math, you’ve looked at the data, you know your margins — and then you decide. That balance of numbers and instinct is what makes hiring for a small business both an art and a science.
So if you’re standing where Kara was — on the edge of deciding whether to make that first hire — know this: the fear is normal. The questions are valid. And with the right preparation, hiring isn’t reckless. It’s the next step in building the business you’ve been dreaming of.
Keep me posted on how you go!
