Congratulations! The time has come when you can no longer run your business alone. Yes, it’s time for you to hire your FIRST remote employee.

You have managed to expand your startup to where it is today, but you have reached the point where you need to hire a helping hand to keep growing. While this is a very exciting milestone, you must also be prepared for everything that comes along with bringing on a new hire. Hiring someone requires you to understand the legal obligations, expenses, liabilities, and time you must invest before jumping into this process.

You need to make sure that you are hiring the right people if you are committing yourself to all these additional responsibilities. To help you with this process, here are some tips on how to hire your first candidate.

How to Know When It’s the Right Time to Hire

While a helping hand is good to have, it is important to first understand if it is the right time to hire. According to Entrepreneur, the cost of hiring and training a new employee is $4,000. That’s a lot of money to be dishing out, so you need to make sure that the cost of hiring someone is both necessary and worth the investment.

To help you decide whether it is the right time for you to hire, take these steps:

  1. Self-assess - Ask yourself, “Can I handle the amount of work I need to complete? Are there enough hours in the day to accomplish these tasks on my own?” Your own health and self-care should come first, so if you feel that you are drowning in work, it might be time for you to hire someone new.
  2. Create a list of tasks - Create a list of tasks and determine what you can outsource to someone else to allot time for yourself to focus on the big issues and expand your startup. If there are 20 or more hours of weekly work, this is a good indicator that it is time for you to hire.
  3. Identify a potential role for hire - Once you have identified the necessary tasks to be completed for your business to operate, you should specify if these tasks align to fit a specific role. Maybe you are trying to outsource your marketing work, so your new hire will be in charge of social media, content with blogs, and SEO, or maybe you just need more administrative work done and no longer have time to spend hours organizing your schedule and completing routine tasks. If you are able to identify work that you can offload your responsibilities and apply to a new position, then that is when you know it is worth the investment of hiring an employee.

How to Attract the Right Candidates

Hiring someone for the role is one thing, but hiring the right person for the role is more difficult than one might think. Getting the right people to work on your team is crucial, and the first step to getting there involves attracting a quality applicant pool. So, how do you attract the right candidates for the job? Read on to find out tips from the VirtualPostMail (VPM) team.

Envision Your Ideal Candidate

Once you have identified the specific role or position you will be hiring for, the next step is to figure out who would be the right candidate to fulfill those job responsibilities. Before you even think about making a job posting, write down candidate criteria such as characteristics, skills, and experiences that you believe an ideal applicant should have.

These criteria go outside the realm of a specific degree or certification someone should have. You should identify the type of personality or team player you want to work with and make sure they carry the same goals as you for the position. Knowing what qualities you look for in a candidate will help you during the actual hiring process.

For example, you want John Doe to be detailed-oriented, passionate, and friendly. John Doe should handle stress well plus have 5 years of customer service experience. Overall, think about defining your dream candidate just like your dream partner! What were deal breakers? What were must-haves? What was on your wish list?

Write a Compelling Job Description

The recruitment process is a two-sided coin. Just how you are sourcing and judging the applicants, the candidates are feeling out if you and you’re right for them too. To attract quality candidates, your job description must be compelling and specific. You want to make those who are looking for jobs feel incentivized to take the time and apply for the position you posted. This is important as a startup since you do not yet have a strong brand name to grab the attention of applicants.

PRO TIP: You should also know what the job entails before you write a job description. If it’s a new role take time out of your day to create a day in the life experience and write down everything that is required.

To find the most qualified talent out there, your job description should have the following:

  • Accurate job title - Candidates should be able to identify what type of work they will be doing based on the title of the job. Don’t get creative here and make your job title something like “Brand Police Officer” instead use something more common such as “Brand Manager”.
  • Background of your company - You need to present an overview of what your startup does, who you are, and what values you stand for. At VirtualPostMail (VPM), the values are Pursue Learning, Respecting Others, Keep Improving, Taking Ownership. VPM ties these values into the hiring process by looking for those who embody those elements in the role they are applying for.
  • Role and responsibilities - This is the most important aspect of a job posting. Candidates need to understand the work they will be expected to do prior to applying for the role.
  • Applicant requirements - You should list the required skills and qualifications (major, certifications, age, personal attitude) that an applicant must possess, as well as preferred skills that would be an added bonus.
  • Working conditions - You need to specify the environment the new hire should expect to work in, whether it is fully remote or in-person, if there is travel required, etc. You should also specify the number of hours per week the candidate will work. Don’t forget timezones too!
  • Wages (optional) - While you are not required to establish a specific pay range in your job posting, it is helpful to specify if the role is paid or unpaid, and if it is paid, whether it is on an hourly, salaried, or commission basis.
  • Benefits and perks - This is a great element to add to your job posting because benefits are a great incentive for candidates when they are job searching. These include your common health benefits, unlimited PTO, sick days, maternity leave, etc.

Maximize Your Job Posting Visibility

The more applicants you receive for the position, the higher your chances are of getting one step closer to your dream candidate. In order to get as many applicants as possible, you need to allow your job posting to be seen by as many people as possible. Post your job on the various job posting sites: LinkedIn, Indeed, Glassdoor, etc.

At VPM, candidates are sourced through Indeed as it has a good structure for setting up job listings. While word-of-mouth and referrals can lead you to a few great candidates, it is usually more difficult to find successful candidates this way, which is what VPM has experienced. Another great channel VPM has explored is university career sources. Students often are looking for internships, and one of the first places they will start their search process is their own university career source.

Make sure to update the position every few weeks/months to make sure your job posting stays current and will be viewed by job searchers. You should utilize social media and your own website to boost the visibility of your job posting.

How to Choose Your Top Candidates

The hiring process can be long and time-consuming, but that is the price you must pay to ensure you are hiring the right candidate. Once your job posting begins to receive applications, it is time to move on to the next step in the recruitment process.

Pre-Screen Candidates

Pre-screening includes reviewing resumes and cover letters to make sure applicants meet the basic qualifications spelled out in the job requirements. Resumes showcase a candidate’s skills and experiences and can highlight whether they would be a good fit for your startup. Cover letters are a great way to gauge interest and learn more about an applicant than a resume can show.

At VPM, the job description (described above) includes a note for candidates to answer three questions in their cover letter. It’s a great way to see if candidates pay attention to detail, which is something VPM values in job roles.

After the resume and cover letter screening, conduct a short phone interview to gauge whether this person is the right fit for your startup, both experience-wise and personality-wise. If the position you are hiring for requires specific technical skills, have candidates take an assessment or give them a project to test whether they are qualified for the job.

Here are some great questions used at VPM that have been effective during the pre-screen phone interview:

  1. What are your career goals? (If it doesn’t paint a picture that matches or is similar to your culture and business it might not be a good fit.)
  2. What are you really good at professionally?
  3. What are you not good at or not interested in doing professionally? (Look out for overcompensated answers such as “I work too hard”, “I am a perfectionist”, “I can do most things myself.”)

Interview Strong Candidates

Schedule an in-person or video interview with promising candidates. During the interview, ask behavioral questions that help you identify how the individual works on teams, deals with authority, reacts to conflicts, problem solves, etc. Their answers to these questions will help you identify if they have the work ethic and style that you are looking for in a new hire.

“I look for fit, whether it’s cultural, value, or role. It’s important to find someone who can naturally fit into the role. Additionally, I look for strengths that may reveal themselves through conversations and phone interviews. If that fits what I’m looking for, if there are little hints or tails or attributes that I can discover through speaking to the candidate, I would also invite them for an in-person/virtual interview,” said Terry, who has a great deal of experience in hiring at VPM, in regards to what he looks for when conducting interviews.

During the interview, start out with some ice breakers before leading into the professional questions. Here are some example questions that Terry likes to use for in-person interviews.

Ice Breaker Interview Questions

  • Tell me something about yourself that would surprise me?
  • Do you have any pets?
  • What are your favorite movies or shows?
  • Favorite sports to play or watch?
  • Describe your perfect meal?
  • What do you like to do for fun outside of work?
  • If you could choose one city to live in for the rest of your life without any limitations, what city would you choose?

Career Interview Questions

  • Looking at your experiences, how do you know if a company is a good one to work for and what is one thing that most of these companies can improve on?
  • Please describe your preferred management style and the ideal work environment to bring forth your best work and effort.
  • How would you describe appreciation in the workplace?
  • Provide an example of when you personally demonstrated ownership or tell me about a time you went above and beyond.
  • Tell me about a time when you took on something significant outside your area of responsibility. Why was it important? What was the outcome?
  • Describe a project or idea (not necessarily your own) that was implemented primarily because of your efforts. What was your role? What was the outcome?
  • Give an example of when you saw a peer struggling and decided to step in and help. What was the situation and what actions did you take? What was the outcome?
  • Tell us about an occasion when you believed you went out of your way or jumped through some hoops to delighted a customer.
  • What is something that might make you angry or deem offensive in the workplace?
  • Have you ever been asked to do something at work that made you uncomfortable? What was it and how did you handle it?
  • What would you do about a co-worker who isn’t pulling his/her own weight and in turn, making you work harder?
  • Tell me about some of the most difficult problems you worked on and how you solved them.

Check References

Reach out to the references listed by candidates to fact-check their work ethic, teamwork styles, and overall ability to do the job right. This way, you have more than the candidate’s words to ensure that you are hiring the right person. However, be aware that references are not the most reliable sources, and you most will hear praise about the candidate, which does not help with your vetting process.

During the hiring process at VPM, Terry has found that references are best to provide another perspective, but should not be a final factor for the hiring decision.

“Most references provided would not take the time to talk. When they do, you’re talking to a stranger who may exaggerate to build up the candidate. You do not know of the reference’s background, work environment, values, so [the reference’s] words also have no value,” Terry said.

Know that the Hiring Process is Not Easy

Sourcing and hiring the right candidate at the right time is a very difficult task, which is why you must prepare ahead of time and identify what you are looking for before diving into the process. Don’t settle or rush to fill the position too because it’ll be a waste of time and resources.

“The whole process is very difficult just to find the right person. We always look for the right person, right seat, in terms of cultural fit, value fit, that’s the person we want to look for. The right seat is skills and knowledge and being physically capable to do the role itself. Timing is a difficult factor of being able to try to coordinate everything to line up. If you need this candidate now, you’re already behind because you need time to hire, to train up to speed,” said Terry.


Hiring your first employee is both an exciting and daunting task. Don’t jump into this process blind. Make sure to confirm that you are at a point where you are ready to hire someone because it’s a lot of time, energy, and money. Once you have done that, take the time to attract quality candidates and ultimately hire the right person for the job.

“Carefully interviewing doesn’t guarantee you anything. It merely increases your odds of getting lucky. I could ask all the right questions, I could do everything perfectly, and the person seems like a great fit, but it really doesn’t say anything if the person cannot perform. It sort of just increases my chances of getting lucky in finding a candidate, but that is good enough for me. I want to increase my chances of being lucky as much as I can,” said Terry. “That is the advice I would provide to people looking for their hires. Just do your best in every aspect of the interview, but understand that you cannot control the person that you hire.”

No matter how you run your recruitment process, you won’t be 100% guaranteed that you will find the right applicant. All you can do is do the best you can to increase your chances of finding that perfect applicant. The steps provided above are a great place to start and will increase your chances of finding and keeping your dream candidate. Remember - you have to kiss a lot of frogs before you get to your prince/princess, good luck!

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