How These 8 Business Owners Knew It Was Time to Hire Their First Employee

How to hire employees
Diana Goodwin, CEO and founder of AquaMobile. Photo courtesy AquaMobile

We talk a lot about starting a business by “working lean” — wearing all the hats and getting things off the ground on your own. When it’s just you and an idea, you can’t afford to hire a team to support you, and sometimes, too many minds only stifle progress rather than accelerate it.

But let’s say you’ve been running your business for a while, and things are getting more complicated. At what point does it make sense to ask for help and start outsourcing some of your tasks — bookkeeping, taxes, tech support, etc.?

We interviewed eight business owners to find out how they realized it was time to hire their first employee, and how they went about finding that person.

Here’s what they told us…

When is It Time to Hire Your First Employee?

The biggest sign it may be time to bring on help? Feeling completely overwhelmed.

“I was being pulled in too many directions,” said Diana Goodwin, CEO and founder of AquaMobile, a swim school that offers everything from in-home lessons to lifeguards for hire. “When I started to feel overwhelmed by the amount of responsibilities I had on a daily basis, I knew it was time to hire some help.”

“I knew it was time to start hiring employees when I literally didn’t have enough hours in a day to do everything, including sales,” explained Julie Austin, inventor and manufacturer of Swiggies wrist water bottles.

“My to-do list was so long that I resented the business I had just started and dreaded what ‘success’ might look like,” said Ben Brooks, CEO of PILOT, a tech startup that helps people manage their careers.

The Affordability Question

Of course, feeling overwhelmed and being able to financially justify a new hire are two separate things. Once you’ve decided it makes sense in terms of productivity, how can you be sure it fits your company’s bottom line?

Max Farrell, co-founder of truck-driver-retention platform WorkHound, cited a great measurement he learned from his mentor, Ted Alling of logistics-accelerator Dynamo: “What hat are you wearing, your $800, $80, or $8 hat?”

In other words, if you can find an employee to take the less-important tasks off your hands, you’ll be able to focus on the work you do best — and the work that delivers the highest ROI for your company.

“For others facing the sense of overwhelm, I would highly encourage you to take a look and make a list of all of the low-value activities you regularly find yourself doing,” said Aaron Lee, president and CEO of digital marketing agency Illuminati Studios.

Add up the time it takes you each week and then multiply that by what your billable rate is. You’ll quickly realize that it’s far more productive to bring in someone who can help you with those tasks, freeing up much more valuable time that you can take back and start billing with!”

Todd Bellistri, CEO of independent benefits management firm August Benefits, remembered a piece of advice his mentor gave him 20 years ago when he was poised to hire his first employee: “If you think you need to hire someone, you need to hire someone immediately — before you have time to ask, “Can I afford it?’ To move your business forward, you need to delegate the things that are holding you back.”

“To this day,” Bellistri said, “I don’t think twice about bringing on a new employee. If I think I need to hire someone, I bring them on. The cost always works itself out through improved productivity.”

Where to Look for the Right Person

So you’ve realized it’s time to hire that first employee — now, how do you find them? Who should you consider?

Here’s what these business owners recommend.

1. College Students

If you’re looking for someone to complete basic tasks for an affordable price, college students are a great option.

Andrew Church owns Bison Hill Stonecrafts, which produces household items like coasters, cheese boards and Christmas ornaments from reclaimed roofing slate, and he also has a full-time job as an Engineer at GE Transportation. He felt “bogged down by repeatable work that [he] could easily train someone else do.”

So he asked family and friends if they knew any college students who might fit the bill as “they typically have the most flexible schedule out of pretty much anyone.” This flexibility was important to him, as he needed someone who could meet with him on the weekends and after working hours.

Goodwin, who runs the swim school, took a similar tack. “I started by going to the local universities and colleges to see if there were students enrolled in business programs looking for work,” she said, “as many of these programs have savvy marketing and HR students looking to build their resumes and gain experience.”

Working with these students often proved to be mutually beneficial, both for my company and themselves. In fact, for several students, what started out as part-time work ended up with a full-time job offer.”

2. Non-Traditional Employees

The freelance, gig-based economy is ideal for new hires for a number of reasons.

“I now try to hire as many freelance, part-time employees as I can,” said Austin. “The cost of having a full-time employee no longer makes sense to me as a small business owner. With websites like freelancer.com and Upwork, it’s much easier to find these people.”

Avi Lele, CEO of stock gift-card company Stockpile, points out, “Just because you need [someone] this month doesn’t mean you’re going to have the same need a few months from now. But once they’re on your payroll, you have to pay them every month — a surefire way to burn through cash.

“It’s also unlikely that you’ll find all of the skill sets you need in one full-time person. For these reasons, it’s usually better to start off by hiring consultants, contractors or advisors who can each help you for a few hours a week or month with discrete parts of your business.”

Brooks agreed: “Some staff I’ve hired have ultimately not worked out, so a contractual relationship is a better structure to get to know someone and make sure it works for both parties.”

3. Referrals

Referrals are a solid way to find workers who have already been vetted by people whose opinion you know and trust.

“I got a referral to a virtual assistant service from a fellow entrepreneur,” Brooks said. “The same for finding a good bookkeeper. I kept getting suggestions of great providers and followed up, secured the team, and haven’t been disappointed yet!”

Your Turn: If you run a small business, have you hired your first employee? What tasks did you outsource, and why?

Kelly Gurnett is a freelance blogger, writer and editor who runs the blog Cordelia Calls It Quits, where she documents her attempts to rid her life of the things that don’t matter and focus more on the things that do. Follow her on Twitter @CordeliaCallsIt.

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