How to Hire the Right Person for Your Business: A Step-by-Step Guide

Most business owners don’t start their businesses thinking about hiring (and firing), managing people, or growing teams. It’s a new skill most need to learn as their business grows, and I love helping clients do this and do this well.

The good news is, it is a skill, and you can learn it.

Sure, it can feel like daunting—whether you’re hiring your first part-time assistant, your first real employee, or a key contractor for your team. But when you find the right person, it can make all the difference to you and your business’s success.

So if you’ve tried before without success, been hesitant to start, or are looking to fill a significant role with higher stakes, I’ve got you covered.

Below you’ll find the steps to finding the right person for the job you need filled.

Get Clear on Who You’re Looking For

One of the biggest mistakes I see business owners making when it comes to hiring—especially if they’ve churned through assistants without ever finding the right person—is not taking the time to define exactly what they need. This isn’t about creating a job description to post online; it’s about getting clear for themselves.

So the first step to hiring—before asking your friends and colleagues for recommendations—is to get really clear on the person you need for your business.

Here’s how to do that:

1. List the specific tasks this new team member will need to do and the “hard” skills they need to have.

What tasks will they need to do right away? What will they need to do down the line?

What might be potential growth tasks or “would be nice” things you’d like them to handle in the future?

What hard skills are required to do these tasks? And—this is really important—do they need to come to the job knowing these skills, or will you train them?

A quick story about training

Many business owners assume they need to hire someone who is fully trained. They expect candidates to hit the ground running on day one.

But let’s be real: Even the most skilled individual needs to learn your business. Some amount of training is always required; you simply have to decide how much you’re willing and able to do.

My first assistant, hired in 2011, knew nothing about online business, websites, or email marketing. I trained her to do everything. I valued her soft skills, ability to learn, and willingness to ask questions over technical experience, which resulted in a fantastic fit for my business. She worked with me for five years, only stopping because she wanted to be a full-time mom when her daughter was born.

My second assistant, who also had no online business experience, was similarly chosen for her soft skills and growth potential. My first assistant trained her, then she worked for me until I was forced to take a personal leave. Both were excellent fits for the work but came to the job with none of the technical skills required of the position.

I mention this because it’s uncommon in online business to work with the same assistant for 5 years, let alone two assistants for 5 years each, both only leaving because of external circumstances, not for reasons for poor fit or individual frustrations. But this is possible when you hire the right person for the right position in your business.

Okay, moving onto the most overlooked part of the job description …

2. List the required soft skills.

Think about what kind of person would work well with your style and in your business.

Do you need someone detail-oriented? Someone who asks questions when they’re not sure about something, instead of guessing and proceeding? Or do you want someone to take initiative, asking for forgiveness instead of permission?

Do you need someone who is quick to complete tasks? Or more thorough and focused on each item?

Someone who thinks about the bigger picture of your business? Or flies through a to-do list because they love checking things off a list?

This list requires careful thought on your part. Who are you as a business owner, and what do you need from the person in this role so both of you are successful in your work together? Having similar qualities to one another in some situations can be helpful but not so helpful in others.

3. List your requirements and expectations.

Next, consider other things that are requirements and expectations for this position.

Do you have specific working hours they need to be available? Do you have an expected response time? Are there meetings they need to attend, and when are those meetings?

Will you be communicating with them daily, weekly, or at some other frequency? How will that work exactly (email, Voxer, Slack, etc.)? What response time do you expect?

Business owners often have expectations in their heads but don’t always realize they have them or think to communicate them to the person they hope to hire. Clarifying these specifics upfront will streamline your process and prevent hiring mismatches.

4. Think through compensation.

Next, consider compensation. This can be simple or complicated depending on if you’re hiring a very part-time assistant or a full-time employee. There are also legal considerations depending on where you live.

Do some research on what the typical compensation is for this position. It can be pretty straightforward, for example, if you’re looking to hire an assistant who is local to you. It can be more complex if you’re wanting to hire someone who will be fully virtual and may or may not even be in the same country as you.

In terms of bigger picture questions:

• Have you done the budgeting for this position?
• Do you know what the employee ROI is? You want to know that the right person for this position will benefit your business beyond their own salary and benefits.
• Do you know what you can afford to pay them before they create an ROI? And how long that window of time is?

When it comes to the job description, you can post the compensation, but you don’t have to. I’ve seen it done both ways.

5. Do a reality check.

Before you proceed, check that you’re not making the same mistake I see many folks making when they come to work with me: Looking for a unicorn.

A business owner might see several bottlenecks in their business, and they try to put all of the bottlenecks into one position (such as an assistant, a sales person, and a social media content creator). But filling that kind of role is unlikely.

So when you look at your list, the one you created based on the steps above, ask yourself if that’s one position or several. Do a reality check before you proceed (and get an outside perspective if needed).

The Hiring Process

Now that you’re clear on who you’re looking for, it’s time to prepare for hiring.

The first step is to think through your hiring process.

Yes, you need a job description. Yes, you need to interview a candidate.

But there are a few other steps in between that folks often don’t consider. For example, how will they apply? How will you evaluate their hard skills? How will you evaluate their soft skills? Do you have a critical timeline for hiring this person?

The second step is to write your job description.

The good news? You have most of what you need from the work you completed above.

Generally speaking, the more detailed your job description, the more likely you are to find the right fit for your specific job.

Here are things to include in your job description:

• Required hard skills
• Desired hard skills
• Information about the training you will (and will not) provide
• Required soft skills
• Desired soft skills
• Expectations of the position
• The kind of business you run, including things like culture, attitude, values
• Compensation (optional)
• Call to action (Do they submit a resume? Fill out an application?)

You can look online for example job descriptions. How lengthy and detailed you get will depend on the position. For example, a very part-time assistant doesn’t need as nearly a lengthy job description as a full-time employee for your team.

The third step is to get the word out.

Once your job description is ready, it’s time to get the word out about the opening.

A great way to start is by reaching out to your network. You can often find great candidates from referrals. You might also reach out to your email list or even past or current customers; sometimes the people who already know and love your business are the perfect fit.

If you’re in online communities with fellow business owners (such as a Facebook group), you may be able to post your job description there.

Assuming you’re looking for a remote position, you could post your job on LinkedIn, Indeed, or a niche industry job board. Some of these options are paid and some are free; what you do would likely depend on the type of job you’re hiring for.

Again, depending on the position, you could look on sites like UpWork for a qualified candidate, or other similar sites.

The fourth step is to vet candidates.

Once you’ve received applications, it’s time to start vetting candidates. This isn’t just about an interview (which I’ll discuss in a moment). It’s about sorting through the folks who have expressed interest to see who might be a good fit, whether that’s reviewing resumes or applications or both.

In your review, yes, you want to look at their qualifications. But also pay attention to the things that matter to you.

For example, if you want a detail-oriented person for the job and someone submitted their resume in a Word file but you asked for a PDF, that might be a flag that they’re not a good fit. Or if you want someone with stellar customer service skills and their email to you felt warm and kind, that might be a good sign.

All of the steps an applicant takes before they interview you is a pre-interview, helping you determine who you’d like to actually interview.

Once you vet the candidates, it’s time to invite your top candidates to an interview.

The Interview Process

Just like the vetting process above, pay attention to the other ways candidates tell you about themselves, from scheduling the interview to how they show up and conduct themselves during the interview. Notice the things that matter as it relates to them doing a good job for you.

The goal of the interview is not only to determine if the candidate fits your team but also to help them assess if the position and your business are a fit for them. Approach this as a two-way opportunity, and you’ll both get closer to the answer you’re looking for.

Set the stage

Begin the interview with a warm welcome. Thank them for taking the time to meet with you. Then set the expectations for duration and anything else they might want to know about the process.

Ask good questions

You’ll want to prepare different types of questions, and the exact questions will vary depending on the type of role you’re hiring for.

Start with some warm-up questions like “What drew you to this position?” and “What do you enjoy about this kind of work?”

Ask some work style questions. Here’s one that I used when I hired a full-time copywriter back in 2019: “This is a remote job with flexible hours, but we’re still a team of Type A action-takers who meet deadlines. How do you manage your time and workload in an environment like this?”

You’ll want to ask technical questions if they’re applicable to the position.

And be sure to ask questions that help you assess the soft skills that are crucial to this person’s success in the position.

Let them ask you questions

After you’ve asked all of your questions, let your candidate ask you theirs. Not only will their questions tell you a lot about them, but they will also help you meet the objectives I stated above: making this a two way conversation so you both see if working together is a match.

Wrap up with clear next steps

Before you end the interview, let the candidate know the next steps. Whether that’s a test project or simply that you need to interview other candidates this week or next, it’s important that they are clear on your process and the timeline.

A key tip from my former mentor

I was working with a mentor when I was hiring a full-time copywriter in 2019, and she gave me some incredibly valuable advice:

Don’t be afraid to ask awkward or otherwise socially inappropriate questions. If there’s something on a candidate’s resume that raises a flag—a gap in their work history, for example—directly ask them about it. If there’s something they say in the interview that has you curious, ask them about it.

Trust that you have that question for a reason, so get an answer to it. Beyond just getting the answer to the niggling question and easing your mind, how they handle that question will tell you a lot about them and their potential as a fit for your company.

Test Projects

Depending on the position, and often critical for higher-level roles or full-time positions, you may want to include a test project for candidates who did well in the interview process. This is a good thing to do where someone’s hard skills are a requirement of the job.

For the full-time copywriter position I was looking to fill in 2019, I needed the person to come into the job with strong copywriting skills that worked well with the brand and style. Yes, we’d provide them with our SOPs and brand guidelines, but we weren’t going to teach copywriting skills.

We designed two small test projects to help us get a better idea of how the candidates would use their skills for our projects.

For full-time positions like this (copywriters, designers, developers), it’s not uncommon for candidates to have to do projects, so the good candidates won’t be surprised by this request.

The project doesn’t have to be complex, but it should give you a sense of how they handle the actual work they’ll be doing for your business.

Choosing the Right Person

After you’ve gone through the interview process, it’s time to choose the best candidate. Sometimes this is obvious, and you make the offer, hope they accept, and take any legal steps required to hire them. Then, of course, you begin the onboarding process.

Other times, you may wrap up interviews without a perfect candidate. It happens more often than you might think, and you have a few options.

You can hire someone temporarily and see how they perform, letting them know it’s a test period of a certain duration. This can give you the flexibility to test the waters without fully committing. If it doesn’t work out, you can start the search again.

You can find more places to post the job description and look for more potential candidates.

If you were wanting to hire a full-time employee, you could close the gap temporarily with a contractor or freelancer while you keep searching.

You can also take a risk and hire the best candidate available, knowing there may be areas where they’ll need to grow into the role or you won’t fully get your needs met.

There isn’t a single best way to proceed, just whatever works for you and your business and the circumstances you’re in.

Finding Your Perfect Fit

When you hire the right person for your business, it’s more than just filling a role. You’re creating the potential for business growth, more freedom for yourself, more expertise within your business, fresh perspectives, better execution, enhanced customer experience, or increased flexibility, to just name a handful—ultimately positioning your business for long-term success and sustainability.

In my experience, the right hire also makes business way more fun.

Whether you’re new to hiring or looking for your first full-time employee (and the stakes feel high), remember that hiring is a skill you can learn.

If you’re unsure about any part of the hiring process, from defining your needs to conducting interviews to making offers, getting feedback or guidance from someone with experience can make all the difference. Getting another perspective from someone who has done it many times before can help you feel more confident and make the process smoother.

In the end, hiring should feel like a win-win. You get a great person to fill a needed position in your business; they get a great work opportunity that fits them.