Deciding to hire your first employee can be a nerve-wracking endeavor. It’s natural to wonder whether you can afford it, how the dynamic of your business will change once there’s someone else involved, and what you’ll do if it doesn’t work out. If you haven’t had experience hiring (or firing) employees in the past, it can feel overwhelming. However, there are steps you can take to maximize the chance that you’ll find the right fit when it comes to hiring and feel more confident about the process.

1. Clearly define what you expect from an employee – and check whether it’s realistic.

If you haven’t had an employee before, it’s easy to imagine a bright future where all the tasks you most dislike are taken off your plate. But it’s not always that straightforward. Now’s the time to do an “activity accounting” of your business: what tasks are done on a regular basis, or on an as-needed basis? Which of those tasks are more strategic or require a longer-term focus—in other words, those you will likely need to continue doing. Which tasks could a new person easily take on, and which tasks would need training? Check your expectations: for the amount of money you’re paying, what level of skill and commitment can you expect? Benchmarking other businesses or job listings can help answer that question. Would the tasks you have in mind for an employee be efficiently done by someone else, or will you need to develop a new approach because right now you do it all?

I highly recommend the book “The E-Myth” by Michael E. Gerber which leads you through this process. Remember, as your business grows, you’ll likely need more employees (or employee hours). It’s best to be aware of the processes and needs of your business as soon as possible so that you can plan for growth rather than trying to catch up with it.

2. Write a good job description, and promote it in the right places for your business.

The job specification is critical for attracting and hiring the right candidate. Make your expectations clear, from the title (assistant level position? manager? a creative or admin role?), through to the mandatory skills/qualifications. As you outline the description, you’ll need to consider where the person will be working, how flexible the hours are, whether you want a trial period (remember to check employment law for where you live), and whether you require references. Including descriptions of the tasks the employee will do and also of the business itself is good practice.

Then, you’ll need to consider where to advertise. If you have a large blog following or social media presence, those platforms may be a great place to recruit people who  have a basic understanding of your business and may be excited about the prospect of working with you. Alternatively, sites like Indeed.com and ZipRecruiter.com are popular employment boards which often have introductory offers, like “recruit your first employee free,” which are great for small businesses. 

3. Trust your gut in the interviewing process.

Above all, you should trust your gut. Having an employee is the same as any other relationship: you have to trust and like the person for it to be successful. You will often have a strong gut feeling about whether this person has the kind of personality you like being around, whether they seem dependable, and understand what the job is about. You’ll most likely be spending a great deal of time with this person, and being able to get along with them well on a daily basis is essential to your well-being. Don’t try to ignore a bad gut feeling. Learn to trust a good one though – although you should of course always verify that a person is qualified for the role, in addition to liking them!

4. Set clear expectations with your new hire.

Expectations should be clear through the whole hiring process and into the onboarding period. It’s worth talking about your own personality: what kind of temperament do you have? Do you think out loud a lot? Are you very quiet and reserved? Do you like working independently or collaboratively? What are your foibles in the workplace? For instance, I often say that I’m very chatty and can sometimes fail to listen – and that while I try my best not to do that, they have full permission to point out when I’m not listening to them!

You can ask them in turn how they like to work, what’s important and valuable to them, and what they dislike. The “golden rule” (treat others as you would like to be treated) isn’t a great one for working with employees because everyone has different ways they like to be treated. Instead, try to follow the “platinum rule”: treat others as they would like to be treated. For instance, some people love lots of praise, collaboration, and input, while other people thrive on feeling that they are independent and not being closely monitored. And the best way to learn that about your new hire is to ask.

However, try as we might, sometimes employees don’t work out, even if we get along with them personally. In that case, here are some thoughts to bear in mind as you let someone go: 

If there is a performance issue, give them a fair chance to improve

If an employee is not meeting expectations, it’s critical to be open and honest as early as possible. Giving an employee the chance to fix issues is the fair thing to do, and often you may be surprised by how much someone can change. Document those discussions, and email the employee with what you agreed, including the problems, and the planned actions the employee will take. If this doesn’t work, then consider putting them on a “performance improvement plan” which clearly lays out the targets and goals they need to meet in a certain time period (e.g., one month), and explains that if they don’t, they may be laid off. If the employee fails to meet the goals, it becomes an easier conversation to explain why you are letting them go.

If things don’t improve, it’s typically a mismatch of skills, rather than a “bad” employee

If, after all your efforts to help an employee improve, they don’t manage to change, you may need to let them go. This can cause great feelings of stress and guilt as a small business owner. The key to remember is: this employee isn’t a good match for your business, but that doesn’t mean you’re saying that they’re a bad person, or that they’re not a good match for ANY job. Instead, it’s just not a good match of skills for th job and they would likely be happier in another role. Explaining where you see their strengths and improvement areas can help the employee understand that it’s a fit issue rather than a failure and that they would likely be much happier elsewhere—no-one likes underperforming!

Jenny Grover

Jenny Grover


Jenni Grover is the founder of the School of Creative Resilience, where she teaches people how to tap into their innate creativity, grow it as a resource, and use it to boost resilience and joy. She currently offers digital courses, in-person workshops, and consulting services. Jenni is also Vice President of the Chicago Modern Quilt Guild.

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