A guide to successfully hiring your first employee

/ 14 min read
Kat Boogaard

There are few things that are simultaneously as thrilling and intimidating as starting your own business. But hiring your first employee? That definitely ranks near the top of the list too.

How can you tell when you’re ready? How do you figure out what you need? How do you manage the hiring and interview process? What about legal requirements you should be aware of? What if you—gasp—make a bad hire?

Hiring for the first time has a bit of a steep learning curve and it’s probably enough to have you breathing heavily into a paper bag. Fortunately, this guide has the answers, steps, and expert-backed tips you need to to demystify the process of hiring your first employee.

How do you know when you’re ready to hire your first employee?

“I need help,” you’ve probably muttered to yourself as you stared at your ever-growing to-do list. Feeling overwhelmed is usually the first bright, waving red flag that tells business owners it’s time to hire.

But simply recognizing you need some extra hands isn’t enough for you to roll out a job description. You need to be able to confidently answer these questions too:

1. Do you need help?

Knowing you need help is an important first step, but your job posting needs to spell out the specific skills you’re looking for—as well as the duties that potential hire will be responsible for. That’s why you need clarity on what exactly you need assistance with.

Do you need someone to market and grow the business? Handle customer service? Work the cash register? Assemble or ship your products?

Know what you’re looking for. That will help you craft the most accurate job title, write a more detailed job description, and ultimately find the most qualified candidates for your needs.

2. Are you prepared to handle the logistics?

There’s a lot more to bringing on a new employee than the hiring process and some on-the-job training. In fact, there’s a heck of a lot of paperwork, regulations, and administration involved.

Do you have an employer identification number? Are you required to offer benefits to employees? How will you handle tax forms? What about health insurance or federal income tax?

If you don’t personally feel equipped to handle those things (hey, we don’t blame you), that doesn’t necessarily mean you aren’t ready to hire. But you do need to look for a payroll service, accountant, or a third-party HR professional who can help you with those crucial things. Compliance with federal labor laws isn’t something you want to trifle with.

3. Can you afford an employee?

Some labor laws are complex, but there’s one that’s painfully straightforward: employees need to be paid. Plain and simple. And that means you need to have the money to pay them adequately, consistently, and on time.

Take a good hard look at your revenue reports and budget to ensure you can handle the financial responsibility of an employee (and of course, how much you can afford to pay them).

“I waited about two years to make the first hire,” explains Jimmy Daly, Founder at Superpath. “I waited until our net income was in a place to comfortably support a hire.”

“I had to save six months’ worth of employee payroll before making my first hire,” echoes Garrett Smith, Head of Local SEO at GMB Gorilla. “I heard enough layoff horror stories to know that I needed to have foresight for employee payroll. When I was able to spare this budget then, I knew I could afford to kickstart recruitment with peace of mind.”

Are you ready to invest the time?

Hiring an employee doesn’t just cost money—it costs time too. And while most entrepreneurs hire because they feel spread thin, be aware that you probably won’t see immediate time savings. You might actually see the opposite.

“The key lesson that I learned from hiring my first employee is that they actually take up more of your time as opposed to freeing you up,” says Ryan Scollon, the owner of a PPC agency. “Regardless of how much experience they have, there will be an element of onboarding and getting them used to the way you work.”

What’s the process for hiring a new employee?

You’ve confirmed that you actually are ready to make a hire. Now what? Your own approach and hiring process could vary, but here’s a general rundown of how things typically flow—along with a few handy hiring checklists to guide you. You can also use talent acquisition software to streamline your hiring process.

Step 1: Determine your needs

We’ve briefly touched on the importance of knowing what you’re hiring for. But before even writing your job description, you need to get into the nitty-gritty of the details of your needs and the position. This includes things like:

  • Job responsibilities: What will this person do?
  • Desired technical and soft skills: What competencies and traits do they need?
  • Employee wages and compensation: What and how (hourly, salary, etc.) will they be paid?
  • Perks and benefits: What employee benefits do you offer?
  • Work schedule: Do you need a part-time or full-time employee? When will they work?
  • Work arrangement: Are you open to remote employees? Are you hiring on-site? Hybrid

Step 2: Post a job description

When you’re equipped with all of the details of the role, you’re ready to pull it into a job description. A few tips to do this well include:

  • Use straightforward and simple language: While it’s tempting to get clever or cute with job titles and duties, you’re better off with intuitive language (so opt for “Customer Support Specialist” as opposed to “Customer Support Ninja”). It’s clearer and it also helps your description show up in search results when job seekers look for those positions.
  • Stay focused on must-have criteria: Have a laundry list of qualifications an applicant needs to meet? It’s smart to narrow that down to avoid overwhelming candidates and potentially ruling out top talent. We’ll dig into this more a little later.
  • Promote your business: Keep in mind that your job description should attract people to your role and company. It’s worth using a short section or paragraph to talk about what your business does and why it’s a great place to work.
  • Keep it concise: You need to provide enough detail, but you’re not aiming for a War and Peace-length job description. Experts say between 300-800 words is ideal for giving information without losing interest.

Once your job description is created, it’s time to post it and share it. You can do that a number of places including:

  1. Your company website
  2. Job boards (both general and industry-specific ones)
  3. Social media

You can also send your job description and application directly to your friends or industry peers and ask them to share it with anyone they think might be a fit. Your goal is to spread the word far and wide.

Step 3: Accept applications and resumes

Once your job description is posted, applications will hopefully start rolling in—provided you made it easy for people to actually apply.

The candidate experience matters, so make sure that your application is relatively painless for interested job seekers to fill out (that means not having to copy and paste all of the information from their resume).

Paperform allows you to create a job application form that’s easy for both you and candidates to use. There’s even a simple job application template you can customize so you don’t have to start from scratch—check it out below.

job application form

Plus, Paperform integrates with Google Sheets, Trello, and thousands of other apps and tools so you can send your form submissions to wherever you want to organise and analyse them.

Ready to create your first job application form?

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Step 4: Evaluate candidates

You’ve got all of your applications—but not everybody can land the job. Once you have enough candidates or have decided to end the application process, it’s time to review everything that was submitted.

This is another reason it’s so helpful to have a clear understanding of your non-negotiable criteria. You can use that as your initial filter when sorting through applicants.

Beyond skills that match your expectations, also keep an eye out for candidates who:

  1. Carefully proofread their application and resume
  2. Took time to provide thoughtful answers to your questions
  3. Demonstrated enthusiasm about your company or the job
  4. Reached out personally outside of the application (like through email or LinkedIn)

Step 5: Conduct interviews

When you’ve narrowed down your initial avalanche of applications, you can focus on the ones that deserve to move forward in the hiring process to the next step: the interview stage.

Exactly how many interviews you choose to do is up to you (although, you don’t want this to drag on forever). Here’s a recommended structure when hiring your first employee:

  • Initial phone interview: This is a short 15 or 20-minute conversation focused on the basics. You can learn a little about their skills and past employment experiences, provide some more information about your company and the role, and generally get a feel for whether you want to move that candidate forward.
  • First interview: You should rule out some applicants through your initial screening questions. From there, you’ll do a more in-depth job interview (usually at least 30 minutes or an hour, done either in-person or via video chat) where you’ll ask more questions about their experiences and strengths. You should come to this meeting prepared with interview questions so you can get the information you need.
  • Second interview: If you had a relatively large pool of applicants in the first interview round, you might do another interview with your final candidates to dig in even deeper and determine the best fit.

Step 6: Make an offer

You did it—you found the one. It’s time to make the offer, which you’ll need to do with a written job offer letter that they can accept, reject, or negotiate. Your offer letter should include:

  1. Position title
  2. Start date
  3. Schedule
  4. Duties
  5. Wage or salary
  6. Benefits

There could be some other aspects—like bonuses, confidentiality agreements, or a statement of at-will employment—that you might want to include too, depending on your company and role.

Basically, your goal is to give the candidate all of the information they need to determine whether or not they want to accept the job.


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Step 7: Prepare your business (and yourself)

You’re eagerly looking forward to your new employee’s first day, but there are plenty of other ducks to get in a row first in order to set both of you up for success.

In this step, invest the time and energy to get your business prepared for bringing in another person, such as:

  • Setting up access and other details: There’s a lot of setup involved with a new employee. You’ll need to get them things like an email address, an ID badge to enter the building if applicable, access to your different tools and platforms, business cards, and any other starting items.
  • Finding and gathering paperwork: This will likely include things like a form W-2 or other tax forms, as well as information about benefits enrollment, retirement plans, and more.
  • Creating an employee handbook or procedures: It’s not just you anymore, so you’ll need to document processes, protocols, and expectations to ensure you and your new employee are on the same page.
  • Mapping out an onboarding process: There’s a lot for a new hire to get up to speed on, so it’s worth the effort to sketch out a loose onboarding process checklist for their first few weeks so you both know what you’ll cover when.

Paperform can help you streamline a lot of this work. It’s easy to create simple onboarding forms to collect the details and information you need from employees—without eye-glazing packets and PDFs.

Job applications, onboarding workflows, and so much more with Paperform.

Start your 14-day free trial now.

Step 8: Onboard an employee

Exactly what your onboarding process will look like can vary. But in general, it should include a healthy mix of:

  1. Job-specific training about their own duties and responsibilities
  2. General training about your company, customers, and processes
  3. Opportunities to connect and get to know you more personally

It’s also smart to ask for feedback regularly throughout the employees first few months with your company so you can make any necessary improvements and hopefully set yourselves up for a long-lasting and mutually-beneficial employment relationship.

4 tips for hiring your first employee (from people who have been there before)

The above covers the typical process for hiring your first employee—from figuring out what you need all the way to bringing them up to speed.

However, getting this right still has a lot of nuance. So, we connected with some other small business owners to get their best advice when hiring for the first time. Here are the things they learned the hard way—so you don’t have to.

1. Hire more for mindset than skills

Sure, you need someone who can actually do the job. But many business owners warn it’s not worth it to get too hung up on technical skills.

“As you hire, consider not only abilities and experience but also behavior and attitude,” says David Bitton, Co-founder at Doorloop. “Since you’ll be working directly alongside them and they’ll be the ones who set the tone for the culture of your company, it’s crucial that you don’t overlook their attitude when making your first hire.”

“The willingness to learn and grow is often just as important as technical skills when hiring new team members,” agrees Milo Cruz, CMO at Freelance Writing Jobs.

And Martin Myer-Krebs, CEO at QMR.AI says neglecting those soft skills and personality traits was one of his bigger regrets when hiring for the first time. “I should have prioritized hiring fast learners instead of experienced people,” he says. “Small companies require people that can shift their responsibilities quickly.”

2. Know your must-have criteria

Hiring somebody new feels like an opportunity to design your ideal candidate—to list out all of the checkboxes somebody needs to satisfy to even be considered.

However, be wary of letting your expectations become unreasonable and instead stay focused on what’s most crucial for the role and your business. “Have some wiggle room, because there are plenty of talented people who are not 100% qualified for the role you are trying to fill,” says Matt Roberts, COO and Co-founder of My Choice Financial.

“Despite not being perfect for the role, most of these people have the enthusiasm to learn about the company and have the right work ethic. Make sure that you don’t miss out on them.”

3. Invest the time in preparation

An employee’s first few days, weeks, and months with your business are a fragile time—an estimated 20% of employee turnover happens within the first 90 days.

If your new hire shows up and you’re completely unprepared, it doesn’t set the tone for a positive relationship moving forward. So ensure you actually take the time to get ready ahead of their first day. If you can’t make that happen, then you’re not ready to hire.

“My impromptu way of working was fine for me, but it wasn’t scalable if I wanted to take on employees,” says Scollon. “The best solution I found was to create templates for all my work documents and processes, making it so much easier for training and keeping things consistent when showing deliverables to clients.”

Roberts noticed something similar and also committed to creating some systems and processes to streamline hiring and onboarding. “When we hired our first employee, there weren’t any systems in place so some tasks weren’t performed at a satisfactory level,” he says. “This made us realize that every employee we eventually hire needs to have a written training procedure they can refer to so they can perform their tasks with little to no help.”

4. Stay patient

It’s understandable that you’re eager to find the right person and have them hit the ground running—and there’s nothing wrong with being enthusiastic. But when it comes to hiring, this old adage applies: good things take time.

“The number one thing I learned from hiring my first employee is it takes longer to find the right person than I thought it would and it’s okay if it does,” shares Marialexandra García, Founder and CEO of Outplay LLC.

Remember that hiring is a process, not an event. Do your best to stay patient and maintain a clear head—you’ll be glad you did in the long run.

New hire, new opportunities

Brining on your first employee is an exciting time. It’s a sign of growth for your business and opens up opportunities you couldn’t pursue if you were still running the show all by yourself.

But that enthusiasm doesn’t totally compensate for the fact that hiring for the first time is downright daunting. There’s a ton to keep track of—not to mention the fear of getting it wrong.

Like anything else in business, it’s normal to feel both thrilled and a little bit of trepidation. The best way to overcome your apprehension about hiring is to be prepared—and this guide will help you do that.

Paperform can help you streamline your entire business, including hiring and onboarding. Get started for free today.


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About the author
Kat Boogaard
Paperform Contributor
Kat is a freelance writer focused on our working world. When she’s not at her computer, you’ll find her spending time with her family—which includes two adorable sons and two rebellious rescue mutts.

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