When Should You Make Your First Hire? Here are 3 Signs to Look For

Making your first hire is essential to your entrepreneurial journey. It shows the business is busy and successful enough to invest in a new set of eyes, ears, and arms. But how to know when to hire your first employee can be a little mind-trip, and not so clear-cut.

We have all sorts of ideas of what we should be able to handle when we decide to venture out on our path (remember that deprogramming I mentioned?). You might be feeling guilt (“I decided to do this; it’s no one else’s burden!”), imposter syndrome (“Maybe this means I shouldn’t be here?”), scarcity mindset (“If I pay for this, I can’t pay for something else”) or some Franken-semblance of the above. 

It can be helpful to know the mile markers of “when” to hire your first employee, but of course, with an intuitive lens — because that’s what we’re doing here, folks! I find that each of these “times” or signs meet in a Venn diagram of “This is when you make a hire.” See if any of these scenarios, or all three, resonate with you. 

When you’re overwhelmed with your workload

There comes a time when you hit your limit, and the normal amount of work you’re used to doesn’t cut it anymore. You’ve taken on more clients, community members, orders, or customer inquiries, and you’re just finding it difficult to keep up. It’s a great problem to have!

Now, what do you need help with? I know better than anyone that when you’re overwhelmed, it can be very difficult to determine what to get off your plate. That’s when the next concept comes in…

Related Article: Work-Life Balance for Founders: 3 Tips to Help You Manage It All

When you know what you don’t know

Sure, you can figure everything in the business out on your own, and you have up until this point. But the reality is, there’s likely a task (or multiple) taking hours of your time that having an extra set of hands — or even better, a talented expert — could handle better. While doodling around on Canva templates can be fun, for example, the results are just not cutting it anymore. And worse, it’s taking your precious hours away from the actual thing you started the business to do (and if you started a business solely dependent on Canva, disregard!). The bottom line is that there is a task taking you hours when it would take an expert much less.  

I spoke to my friend Faith Streng of Faith Streng Healing about the intersection of being overwhelmed and knowing what she doesn’t know as she embarks on her next hire. One area she recognized needing to invest in or hire in is PR and marketing for her business. Previously, the timing never felt right. 

"But now as I'm spending more time building things, I have less time to devote to marketing myself," Faith said. "And I'm at a point where I know to get to the next step, I need experts, because I'm beyond learning things on my own and implementing that. And I'm ready to take that off my plate." Listen to our full conversation here. 

When you’re no longer interested in certain elements of your business 

This is the perceived lesser evil of the three, but from an intuitive sense, it’s paramount to recognize. When you’re not feeling joy or flow doing a task in your business, it creates a layer of effort that your end user will feel, even if they can’t put their finger on it. 

I recently rebranded my business, and during this process I took a look at a forecast email newsletter that I wrote religiously and was very well received, with an average 50% open rate. Eventually, I began to resent the time it took me to write the email, usually on Sundays, so I could get the forecast to my community in time to start their weeks. Because of the uncanny engagement, I hired a staff writer to help me with them a few months prior. Overall, hiring someone should focus the business in a real way, instead of just winging it.

For me, this uncovered another lesson around hiring. Ultimately, that newsletter was one of the first things to go in the rebrand. Despite hiring a writer to help, I still felt the pain of getting to the desk every Sunday to do the two to three hours of last-mile editing work to ship it out. What was once a delightful way to connect with my community no longer brought me joy and, even worse, brought me angst. I had tried every which way to keep it alive, but I didn’t ever want my community to feel that damaging second-hand resentment. 

The inability to solve this problem by hiring someone was one of the first clues that something was out of alignment with the business model altogether. So, I’m glad that friction existed to push me into uncovering it. If making a hire isn't solving the pain point you hoped it would, it's often a signal that you need to take a deeper look at the root cause.

Next, we’ll talk about who your first hire should be, which I’m sure you’re already percolating and thinking about! 

Want more content like this? Explore other posts from Alex on our blog, and check out her podcast Capricorn Rising Inc., a guide to help leaders strengthen their intuitive skill sets and follow their calling.