Business Management / Human Resources

7 Ways You Know It’s Finally Time to Hire Someone

Jeanette LeBlanc

Updated: Aug 04, 2021 · 9 min read

Toolkit for download in this article

when is it time to hire an employee

Do you suffer from the common entrepreneur ailment, Jack-of-all-trades syndrome?

Symptoms of this common ailment include:

  1. Extreme reluctance to give up control of any of the pieces of an increasingly complex puzzle
  2. Avoidance of hiring stemming from your intimidation with the hiring process
  3. Not enough time to do everything, yet not enough time to find someone else to do it
  4. Steadily decreasing time to spend in your zone of genius and a frustrating sense of being bogged down by all the rest
  5. Frustrated customers, lost revenue and stagnant growth

This doesn’t just apply to newbie entrepreneurs. Even if you’ve been around the small business block, earned your stripes and have a solid support team, you may still find yourself stuck in the same trap. 

Sooner or later, most small business owners reach a moment of truth: Your dreams of success require you to expand your team.

For a small business, whether you are hiring a sales rep or an administrator, every  knowing when to when to hire employees makes a significant impact. Unlike in a large corporation, every person you invest in hiring will have the potential to change the game. 

When is it time to hire an employee?

To find out, we asked seven entrepreneurs about hiring their first employee. It turns out that many of the motivations remain the same, whether you’re adding your first team member or your tenth.  

1. Are you working yourself to the bone?

All work and no play makes for one burnt out entrepreneur. If your small business has grown to the point where your hours are steadily increasing just to complete the bare minimum of your work. it’s probably time for an addition. 

“I knew it was time to hire my first employee when I was working 30-40 hours a week just on client work, not including accounting, sales and other aspects of running a business. I realized that in order to grow my business I absolutely had to hire an employee and offload some of my tasks and responsibilities.” –Jeff Oxford, 180 Marketing

2. Are you stuck focusing on survival over growth?

It doesn’t take too long for most small business owners to learn that it’s far too easy to get stuck in the monotonous but necessary tasks involved in logistics and operation—at the expense of the vital growth activities that will move your business to the next level. 

“I figured out my time spent working on sales growth was much more valuable than the unsustainable hours I was spending on customer service and other administrative tasks. In hindsight, I wish I had hired someone sooner so that I could have focused on higher value-added activities. I was penny wise and pound foolish.” –John Kinskey, AccessDirect, Inc.

3. Is the quality of your work suffering?

Yes—you are good at what you do. Really good. But chances are you didn’t get into your business to become an expert in customer service or accounting or distribution. When you hit a growth point, all the other things compete with your zone of genius for your time, and work suffers across the board. 

“For me, it was when I had been up until 2am every night for the sixth week in a row and still had more work coming in than I was getting out. When quality of service started to slip and clients had to wait longer and longer for projects I knew I needed help.” –Joshua Watson, Iron Rock Software

Is trying to be the jack-of-all-trades turning you into the master of none—at the expense of your business dreams? If so, it’s time to step back and assess how expanding your team may improve the overall quality of your product or service.

“The stress of doing too many things meant I did poorly at all of them. I was spread too thin and couldn't do the stuff I did best. I'm really good at marketing and sales calls, but constantly being distracted with other fires that needed to be put out affected my ability to do the other things effectively.” –Allen Walton, Spy Guy Security

4. Are there not enough hours in the day?

You’ve got exactly the same hours in your day as Beyoncé has in hers. And as an entrepreneur, you probably make good use of every last one. But no matter how you slice it, there are still only 24, and even Queen B can’t make those last any longer than they do. 

“I started to receive more orders than I could make by myself. My first employee was a former co-worker who had the right skill set, was reliable and could produce quality. I took the time to train him, and he is now my right-hand guy. He knows the processes and helps with everything from design to delivery, it was the best decision I've made.” –Thomas Brierton, Bryer Leather

When you’ve maxed out all your work hours and your play hours and start stealing from the few left for eating and sleeping, something has got to give.

“I was capped out. I could no longer take on more clients. Between the current billable hours and the back end work there was just no more time. I brought on another service provider and trained her how to work with our clients and then changed the way I spoke to new incoming clients. Not as an "I will do this for you" but more as a "the team will do this for you.” That was two-and-a-half years ago. Since then I have grown that team to what we are today. The key is to stop working in your business and instead work ON your business.” –Kellyann Schaefer,  Task Complete

5. Are you ready to let go?


Nope—I’m not talking about the classic 80s Janet Jackson tune—I’m talking about your difficulty handing over the reins.

Don’t fret—it’s likely the most common entrepreneurial trait, and it’s likely a big part of how you made it this far. But there comes a time where you’ve got to loosen your hold. Contrary to popular belief, this may be just as difficult the tenth time you hire a new team member as it was the first time. 

"At first it was hard to let go and trust that the work would be done to my expectations. I was able to overcome the ‘If you want it done right, you have to do it yourself' mindset by slowly offloading more and more responsibilities over time. It was definitely the right choice for my business and allowed me to focus more time on sales and significantly grow my business." –Oxford

6.   Are you losing your passion?

“I was starting to lose the passion in my business because I was balancing the ‘doing of the business’ plus the marketing and building of the business." –Schaefer

Chances are, when you began your business, you were filled with passion. The long hours and late nights and the challenges didn’t faze you because you were on fire with your ideas and your desire to create a life on your own terms.  

But onto even the most passionate life, a little reality may fall. And it’s not uncommon for small business owners to get bogged down in the challenges and constant logistical and financial demands of entrepreneurship.

But guess what—that passion is vital to your success. The one thing none of your competitors can copy is your spirit and drive. The very things that make you, you and set your business apart.

Sometimes, it’s that lagging passion that serves as the strongest indicator that it’s time to grow and hand of some of the passion stealing logistics to someone else—so that you can regain the fire that got you started in the first place. 

7. Can you afford to (or better yet, can you afford NOT to)?

“The math added up. Before I hired someone, I added up how much money they would be making and compared it to the amount of money that I thought they would help me bring in. I ended up making a huge mistake - I undervalued the employee. He was such a huge boost to my business that it was obvious within a week that it was the right decision.” –Walton

No doubt, making the decision to expand your small business team is a difficult one. But there will come a time where you will be faced with a decision; on one side lies growth and expansion, and on the other, stagnancy or, worse, small business failure.

Hiring is not a decision to take lightly, after all—most employees expect a real paycheck. But, for growth and success, it is ultimately essential. 

“I have been in business for fifteen years, but did not hire my first employee until eight years ago. I finally realized I was getting away from the core aspects of my business that actually made me money. I was fielding the phone calls, answering the emails and packing the products for shipping. I started neglecting optimizing my website, listing my products on Amazon and putting great content on my eBay listings. All these tasks that needed to be done on the customer service side and the logistics side were hindering me from growing. I still wanted to give awesome customer service and ship items out the same day they were ordered, but I also wanted to grow. My only way to grow was to hire an employee and train them to do the things that were slowing down my ability to concentrate on growth but still a necessity to the business.

Hiring employees was the best thing I ever did. It took me several years to realize that I cannot do it all. With the new bodies in the business, I was able to concentrate on growth. I now have 16 employees and we have grown from $600K a year in 2007 to being on pace to easily break $10 Million this year.

If you think you need help, you probably do. Bite the bullet and hire someone."  –Steve Acree, Seismic Audio Speakers

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