Your First Hire — When and How to Do It Right

Running your own business is exciting. And if you’re reading this blog, then you’ve been doing it all on your own — juggling every role and maybe contracting out a few as your business grew. Now, however, you’re starting to notice that running your business takes more time and energy than it did before. It might be time for some real help…full-time help.

The idea of bringing someone new into your organization can be scary when you’re used to flying solo. Those fears typically produce the same questions:

• Do I have enough money to pay someone a salary?
• Is there really enough work for a full-time employee?
• How do I choose someone reliable?
• I wear so many hats right now, which role should I hire for?

Rest assured, all of these uncertainties are normal. But they shouldn’t stop you from doing what’s best for your business.

Two questions I get asked all the time are:

1. When do I hire my first employee?
2. How do I choose the right person and the right role?

The short answer is: It depends. I know, classic marketing response but it’s true. Every business and business owner is different, so the exact approach to hiring people will vary. Luckily, though, there are some simple questions and activities you can go through to determine if it’s time to take on your first employee and who that should be.

When to Hire

Depending on your business (and personality) this could be one of the toughest or easiest decisions you have to make. Some people are energized by bringing new hires into the fold while others are hesitant to let go of some control. The key is finding balance both in your personality and the timing.

If you hire someone too soon, you likely won’t have enough work or revenue to sustain an employee. Remember that full-time (and some part-time) employees come with added costs like payroll taxes, employee benefits, health insurance, and more. If you don’t have the cash flow to support these additional costs, it can strain your business finances and eventually ends with you having to let someone go and recoup months’ worth of revenue.

If you wait too long, then you might miss out on new business because you don’t have the capacity to take them on by yourself. Or worse, the quality of your work could suffer because you're stretched too thin trying to manage your clients and business operations.

There are a few telltale signs that it’s a good time to consider your first hire:

• You’re consistently hiring independent contractors or freelancers for at least 20 hours of work a week. This shows you have consistent work that you can’t do on your own. Hiring an employee to take this on gives you someone dedicated to your success and able to focus all their efforts on your clients.

• You consistently sell similar services. When your clients are all requesting similar services or packages, it’s often wise to hire someone who can handle those tasks. For example, designers, copywriters, developers, etc. This also lets you carve out a speciality in your industry.
• Your client engagements are profitable but overly time-intensive. If you’re meeting your financial goals with clients but spending too much time keeping those accounts afloat, then you need help. Hiring a full-time account manager can take some of that work off your plate so you ensure you’re continuing to provide great service.

Do any of these apply to you? Some businesses will face just one while others might be in the thick of all three. Whatever your situation, if these sound all too familiar, then it’s probably time to start thinking about hiring.

How to Hire

Step one is knowing when to hire employees. Step two is navigating the hiring process. I know it can feel overwhelming at the start, so we’ll break it down into easy steps. The trick is to stay focused on your agency values and work backward from there.

I know what you’re thinking. “But Tyler, what about their skill set, education, and experience?” All of those things are important but keeping your values top of mind is critical to successful hiring. New employees should not only be capable but also a good match for your agency. That’s the difference between a long-term team and a revolving door of short-term hires.

Be on the lookout for people who match your core values and will exemplify them in their work. You can see this in their personality, character, work ethic, attitude, etc. 

Finding the Right Person

Determining what you need from your first hire starts with figuring out what you can reasonably accomplish — both day-to-day and long-term — and what important tasks are left over. To help me assess this, I like to use the Covey Matrix.

This matrix helps me determine what’s most important and what can wait til later. Everything in Quadrant 1 needs to be handled first, with Quadrant 2 prioritized right after. These two boxes house tasks that will impact the long-term success of your business, and they’re where you should focus when considering your first hire.

How many items in Quadrants 1 and 2 can you accomplish on your own? (Keep in mind, you also need to eat and sleep and be a person outside of work.) What items are frequently getting left behind or put on the back burner?

Your first hire should be someone who can help with important tasks and keep them from falling through the cracks. You want to focus specifically on the ones that are tough to contract out — typically these are client-facing roles. This is how you ensure you get the most from your first employee but also that they’re doing the most for your business. 

After you figure out what tasks need to be done, you should also consider what you like doing. Who you hire will be dependent not only on your business needs but also who you are as a business owner. 

In my case, I love building things but I’m not as great at maintaining them. So when it came time to make the first hires for my agency, I focused on finding people who could help me stay on top of client accounts. I kept the sales role to myself for longer because I loved doing it and was pretty good at it.

Many of us small business owners are idea people and we need a support staff to help us implement, execute and edit those ideas. The editing part is a critical aspect of your first hire. You want to hire someone who can (and will) tell you no when your ideas either aren’t worth pursuing or need some fine tuning. This gives you a sounding board to test things out on and often that person will help you stick to your growth path instead of wandering into the weeds.

Bonus: Where to Look for Your First Hire

Knowing where to find your first hire is just as important as the when and how to do it. Job seekers are everywhere, but where are the most qualified candidates for your industry?

Job boards like Indeed or Glassdoor are easy places to start. Some people also leverage their social media accounts such as LinkedIn or Facebook to advertise openings. If you go this route, be sure to include the job title, job description, responsibilities and the qualifications you’re looking for.

My primary advice, though, is don’t feel restricted to the traditional recruiting channels. Your first hire might be someone you met at a conference last year or a contractor that you were impressed with. As you go through life, you’ll meet hundreds of talented people in your space that might end up being a perfect fit for your business. Keep them in mind when it comes time to make your first hire and reach out to see if they’re interested in being part of your organization.

👉 Not sure where to start looking for your first hire? Let me know and I'll send you my top 8 places to find your first hire.

Always Be Prepared

Half of owning an agency is planning for what’s next or what could be next. When it comes to your staff, always be on the lookout for who should be the next addition to your team. 

If you work with or develop a relationship with someone who is an obvious cultural fit for your company and working style, make a mental note for the next time you’re ready to add to your team. You might not know exactly what role they fit into yet, but sometimes you just know they’ll make you and your company better.

Want to learn more about hiring for your agency? Sign up for my “Getting Out of Your Own Way” free course to learn how you can grow your agency.