Small Business Hiring: is it for you, when, & where to begin?

Hiring your first – or next – employee is one of the most important decisions a small business owner can make. Do it too soon, and you may strain your cash flow or bleed money (and frustration) on duplicated efforts. Wait too long, and you may feel too burnt out and busy to make the right hire. So how do you know when it’s the right time for small business hiring?

Personally, I believe that hiring is one of the most (perhaps the most-most?) important moves a Small Business CEO can make. Because your team is small, perhaps even just yourself, adding another body, brain, and energy to the mix will have major effects, and they can be incredible or debilitating.

So today I want to walk you through:

• how to know if a hire is right for you,
• the tipping points that indicate: it’s time, and
• where to begin hiring (even if you’ve already been doing it).

1. How Do You Know If an Employee Is Right for You?

Before looking outward for the “right hire,” look inward. What kind of business are you building? In this post on long-term business vision, we outline 3 small business end games:

• Lifestyle: maximized for flexibility and owner take-home pay,
• Legacy: designed to grow beyond the owner for sustainability, and
• Start-Up: built to scale ASAP, boosted by outside investment.

If you’re building a Lifestyle business, you’ll likely remain solo (perhaps with contractors). Your motivations in staying small are often: protect your time, retain all the money you can, and/or constrain your responsibilities. After all, building and nurturing a team is a momentous responsibility. Anyone embarking on this path must understand this.

But on the other hand, if you’re building a Legacy business or Start-Up, hiring is essential to scale operations, serve more clients, and build a company that can run without you.

I’d be remiss to not say: the case for a Lifestyle business is compelling. Who wouldn’t want more flexibility, money, and little responsibility?

But there is a reason – nay a deep purpose – to the build beyond yourself: giving your business, your employees, and your career a future.

JUST DO IT ACTION

What’s your long-term vision? Don’t think too hard; go with your first intuition. Are you building a solo practice or a business to live beyond you?

Your answer determines how essential hiring really is.

2. What’s the Right Time to Hire?

Most business owners hit a point where growth stalls—not because of lacking demand, but because they’re doing everything themselves (and not well, at that). If you can feel yourself creeping toward this ledge, ask these questions:

1. Are you spending lots of time outside your zone of genius? In other words, do you spend >20% of your time on things that drain you?
2. Are you turning down new business?
3. Could a hire generate or save you money?
4. Is client service slipping?
5. Are you missing new revenue streams or creative opportunities?

In other words: are you the bottleneck to growth?

These questions come from Kitces’ “capacity wall” model. Though his subject matter is financial advisors, the themes can be applied to any business with a service offering. TLDR: he believes you should hire is you’re consistently working at or above capacity; and therefore, the business is suffering or stagnating because of it.

JUST DO IT ACTION

Grab a notepad or your Notes app and answer each of the 5 questions honestly. If you say “yes” to any of the above, you may be at the hiring tipping point.

3. Where Should You Start?

Before posting an “Apply here” post on Instagram (I see you, creative business owners ;)), take these steps to prepare wisely. And as always, the more thorough the prep, the easier the process.

✅ Track your time.

If you’re not sure what takes the most of your day, it’s time to dust off Toggl (or any time-tracking tool) and log your work for 2 weeks.

✅ Get clear on what the business needs.

How much of your work can be standardized through clear processes? Documenting workflows now will save major onboarding headaches later.

✅ Automate everything you possibly can, first.

You’ve heard me wax poetic about this. Technology can do so many things that we used to have to hire for. Automate anything and everything you can first; then hire for roles that require critical thinking, creativity, or a personal touch. It’s how you’ll get the biggest bang (and scalability) for your buck.

✅ Plan for impact.

Once this role is trained, what will you do with the time they free up? Focus on high-impact activities: generating more business, launching a new product, refining systems, or developing new revenue streams.

✅ Know the real cost.

According to the Bureau of Labor Statistics (and personal experience/math, ha), salary only accounts for about 68% of an employee’s total cost. When you’re estimating the cost of your hire, add 20–30% for taxes, insurance, and benefits. Then run a 1-year forecast with and without the hire. What expenses might they eliminate? What revenue could they protect or generate?

JUST DO IT ACTION

Choose 1 energy drain to eliminate or automate. Do it for 2 weeks, then come back to your energy drain list and keep eliminating and automating until you reach an item you need to delegate to someone else.

Final Thought on Small Business Hiring

After reading all this, you may be thinking, “Nooooo thank you. I will opt for a solo Lifestyle business, after all.” If so, I understand. Small business hiring and building a team requires immense effort, money, and the piece that many don’t speak of: emotion. And real talk: none of these have quick returns; they’re all long term investments. You won’t do it “right” the first time. It’ll take experimentation, failure, and climbing out of the learning pit to try and try again.

But here’s my advocacy for small business hiring. I believe that for creative, small businesses, there’s no way to make a greater impact, skillfully combining business and humanity. To create career and financial opportunities for people by doing incredible work, paying them well, and caring for them. Not to mention multiplying the impact you’re able to have through serving more clients.

If you’re a small, creative business with a team of 2-3 employees, and you’re feeling stuck… you want to do things differently: hire better, you want the team to feel better, or you need them producing better work, we’d love to see if Ellevated Outcomes can help. You can schedule a consultation. We’ll ask you all about your current state, your goals, and your pain points; and we’ll (always honestly) tell you if we think we can help you make your next move with clarity.