A Complete Resource on Hiring Your First, Second, or Fiftieth Employee

Frustrated and need to hire

As an entrepreneur, there comes a time when you need, to hire in order to grow and scale your business. So far, business has been good, but it seems as if you have plateaued, that perhaps you have reached the maximum output that you can do.  You need some sort of push to regain the momentum that got you there, and hopefully, gets you to the next level of your plan. Whether you are looking to hire your very first, second, or your 50th employee, it is easier said than done.

And before you post on Facebook, Twitter, and LinkedIn “I am looking for a…”, be sure that you are not hiring for the wrong reasons.  As a past recruiter, I have seen it happen over and over again, entrepreneurs hiring for the wrong reasons.  As an entrepreneur, I totally get it now, I understand!  There are times when I feel like there is nothing more I can do to grow the business.  And at that moment of weakness, I become desperate and want to hire the first person that walks in the door.

As mentioned, you are at wit’s end. You’ve read all the blogs, listened to all the podcasts, spoke to advisors and the general consensus is that you need to hire to grow your business.  You know what you do?  Obviously, you go out and hire someone

Great, hire someone, but ask yourself, what will they do?  Have you figured out what their responsibilities will be? Will they be your assistant, your general manager, or your rainmaker?  An even more difficult question I have for you, do you have a job description?  If you can not answer any of these, STOP!  You need to hire, but you need to plan and prepare.

Lastly, don’t hire the first person that walks through the door.  More often than not, it may be someone you know.  Someone you trust.  Yes, I get it, the two of you get along and may be able to work together.  Just know this, everything changes when you become the boss.

To help you out, you may want to think of hiring a co-founder, if you are the only person in the company.  Or better yet, hire the perfect co-founder, someone who wants to, and able to, take a lot on.  Finding an employee with co-founder qualities may be significantly easier than it is to find a co-founder.

A co-founder would be perfect because they possess the following qualities:

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  • Complementary skills
  • Similar vision and values
  • Openness to learn
  • Passion or energy
  • Emotional intelligence
  • Flexibility
  • Honesty


Hiring with a co-founder mindset is essential for your first employee as they can, and may be your longest employee. That person can eventually be someone you trust with knowing everything about the business. Of course, in an ideal world, the first hire, can be someone you elevate through the business, and perhaps, someone who can take over the reins when you are ready for a new challenge.

Ok great, you tell me you are not desperate, know what they will be doing, and promise you will not the first person that walks in with a smile and heartbeat. The question then becomes, when should you hire and the answer is quite simple, hire when the tasks to be done will generate money.

[blockquote]Hire when tasks to be done will generate money[/blockquote]

As you close more deals, money eventually starts to trickle in and you may look to hire help but not sure where.  In all business, they say that any job function can either be one of the two:

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  • helps the business make money
  • helps the business saves money


The common denominator is money.  If the role you are looking to fill falls under these categories, you are on the right path.

For any business that is starting up and growing, it is key to generating as much revenue as you can before looking to save on operation expenses.  And, really, let’s be real here, what and where are you looking to save at the outset of the enterprise journey anyways (having said that, I would love some insight on this if you have any)?

Let’s take a look at the job roles that have a direct influence on revenue.

Creating the Product

At the point of hiring, most small business owners already know, hopefully, the products and/or services that they are offering and will most likely not need any help to define this.

Of course, if you are technology startup company, where technical know-how is needed to not only get the product launched but to also expand the features to meet the demands of a growing customer base, then this may be the first spot.

Marketing the Product

Marketing, where do we begin? Marketing is essential to building awareness around the brand and service. But what comes first? You can start with social media marketing on Twitter and Facebook.  Or start with trade shows.  Or perhaps, you may want, to begin with, brand marketing.  The path is unlimited and will depend on your product and customers.

So where do you start? Begin with a process of the work that you are currently doing. For example, social media is the low hanging fruit for many new businesses because of the low cost of entry, that being zero. Social media can be effective when done right. Unfortunately, many entrepreneurs do the bare minimum because they have 25 or more things to do that day.  And doing the bare minimum in social media proves to be ineffective and worse, a waste of time.

The good news, training on social media is minimal when you are looking to fill this role.  The person will not only understand the medium but may be an expert in it.  You can hand off everything you have done to date, discuss what you want to do, and go.  With a marketing strategy and someone executing, expect traffic to your site and sales leads to increase while you focus on other revenue generating activities.

Other than social media, you can look at bringing in a domain expert.  Someone who specializes in brand marketing, strategic partnerships, inbound marketing, advertising, or even tradeshow marketing.  By doing so, you will be expanding your marketing breathe that will help bring in more leads which create more revenue.

Supporting the Product

As your business grows, so do the customer support calls. Providing effective and timely support when the calls are essential to building the trust of the customer, which in turns, create happy customers who would be willing to refer you to their friends and colleagues.

Customer support is the relationship you keep with your customer.  From the first contact to onboarding and ongoing support, and hopefully, other business or advice.  An ideal support person listens to the customer and becomes their champion in-house ensuring that their concerns are heard and acted on.

Specific Skills Needed? Hire a Freelancer!

When the job is not defined, you may need to hire for a specific skill set that is needed.  For example, for a technology startup who is looking to expand their feature set may need someone who can help them on server architecture in order to get over the hump and grow.

Or perhaps, you are a small business owner who has no technical skills but needs to build and maintain a company website.

Keep in mind, when you are hiring for a specific set of skills, ensure that it is for a specific job or project.  If it is project based, like building and maintaining a website, perhaps you may want to look at hiring a contractor or freelancer as it would not be ideal to hire a web designer in house.

Same goes for specific development projects, you can easily source experts on sites like upwork.com and freelance.com.  There are many benefits of hiring a contractor and freelancer, which can be all you need at this point of your business

The Hiring Process

The hiring process can consist of many steps.  For the context and purpose of the article, I will just go over the top 4 things you need to do.

Determine What You Need

As I mentioned above, not only do you need to determine what you need but be sure to have a job description written beforehand.  Otherwise, you will be hiring a person and have no idea what they do.

In is not difficult to create a job description.  I know many of you are thinking, I will just google the job title and copy and paste it. Please don’t.  You can simply start by documenting what you do currently, and what has been on your wish list for the last umpteen months.

For example, if you are managing “social media” currently but only have time to post one thing a day, you can start by writing that down and adding everything that you wish you had time for.  For example, it could look like this:

For example, it could look like this:

  • Schedule new status updates for the week
  • Find applicable and shareable content
  • Create and share a new post each day
  • Interact and reply to all engagements
  • Start a twitter chat to engage audience
  • Write a new blog article once a week
  • Create and execute video marketing campaign
  • Create and execute paid advertising campaign
  • and etc.

A list of tasks is an ideal starting point for a job description.  It is specific and measurable.

Seek Out Candidates

Seeking out candidates is much easier said than done.  As a former recruiter, I made a living because business owners and stakeholders were too busy to not only search out candidates but to find the right now.This, as an x-recruiter, is so much easier said than done. I made a living because business

Don’t get me wrong, I am not advocating on hiring a recruiter, but just want to make the point that you are not only hiring for skill, but also for culture fit.  And hiring for culture can trump skills, as you can train a skill.

[blockquote]you are not only hiring for skill, but also for culture fit[/blockquote]

Interviewing and making an offer

Guide to startup interviewingInterviewing is a key determinant on hiring a someone, so before your interview, be sure that the person looks good on paper. Whether it is a resume, their LinkedIn profile, their portfolio, and etc. You obviously want to protect your time and the time of the candidates as the interviewing process can be long and drawn out.

Interviewing is a key because it gives both you and the candidate an opportunity to meet one another. Most importantly, you can set expectations on the job.  The last thing you want to do is oversell or undersell the role to the candidate because setting realistic expectation is important for retaining great candidates.

Making it official

Once you’ve decided on the perfect new hire and made an offer that’s been accepted, it’s time for the paperwork.

You Successfully Hired the Perfect Candidate

Congratulations, you have the perfect candidate all signed up and they are ready to start on Monday. Bear in mind, your job is not over, half the battle was hiring the right person, while the other half is keeping them.  Be very wary that there is a very competitive market out there for keeping and retaining top-notch employees.  To stay competitive, a successful onboarding does not end on day one, onboarding should take at least 90 days.


A successful onboarding does not end on day 1, onboarding takes at least 90 days.  So what can you do to ensure that everyone is happy?

First off, get ready before they start.   Be sure that you provide a comfortable workstation, something that they can call their own. Be sure that it is clean and bright. The last thing any new employee, myself included, wants to be placed in the back storage room, as you promise to move them when you grow.

Provide all necessary business tools need to deliver the job which can include a computer, telephone, and any supplies that they will need.

Lastly, be sure to create their email address, the phone number, and extension so that they can get their business cards made as soon as possible. And added touch would have their business cards ready when they get to their desk, alongside the employee handbook, org structure, and phone directory.

A nice touch is to provide a nice gift. It can be a simple folder with a logo, a travel mug, or pen. It’s a great feeling when you start a company because you feel like one of the team already, you belong.  Besides, who doesn’t like receiving gifts?

Create an agenda for the first week

You need to resist the urge of throwing your new employee into the deep end, however, prepared they may tell you they are.  Rather than throwing them into the deep end, with a swim and sink mentality, create an agenda that will ease them into the company. An agenda not only helps them get their feet wet but also helps you schedule your time and expectations when onboarding them.

An agenda not only helps them get their feet wet but also helps you schedule your time and expectations when onboarding them.

Some things that you may want to include in in the schedule are:

Help new hires get the lay of the land

It’s a whole new world and it will take time for them to become comfortable in their new environment. It would be nice schedule some time to show them the lay of the land. Show them where the kitchen is, how to make coffee, tell them who makes the best coffee. Show them where the bathroom and exits are.

While doing the walk around, be sure to introduce them to EVERYONE in the company including pets. If you have an aquarium, let them know how and when to feed them.

I also like to go the extra mile and take them out of the office and show my favorite spots to eat, where I get coffee, where the closest yoga and gym studios are.

Block off time for orientation

Schedule in time for a formal orientation to go over the
Plan a managers meeting
Set expectations, open door policy

Cover important work processes

Lastly, be sure to set aside some time to go over some key business processes including job specific systems. This can include, but limited to

Corporate Website

Review the company website, key areas for products, support, and contact us. Whether they are in a marketing or support role, your employees need to be shown the website and know how to find things

Communication Systems

Go over all communication systems including telephone, email, and instant messaging. What are the policies of using them, and when and where to use it? With today’s ever changing environment, every company has a favorite communication channel to use for different instances.

Email Signature

A very simple thing, but do not assume that everyone knows how to update their signature. Even if you already set up their signature beforehand (as mentioned above), it is a good idea to show them how to update it and what to include in it


You may have gone over the phone system in the communication systems section, but it is essential to show them how to set up their greetings. Show them how to set their regular greeting, they’re out of office greeting, and their temporary greeting. Let them know the difference and perhaps what to say. Go over how to check voicemail, many organizations are using older systems where you can only check by calling in and/or using the desk phones. Some organizations have up to date systems that send voicemail directly to their inbox in their email. In either situation, now would be a good time to send a test voicemail.

Business Systems

  • Customer Relations Management (CRM)
  • Service Desk
  • Billing Systems
  • Marketing Automation Tools
  • Social Media
  • And so forth, and so on

The First 30-60-90 Days

First off, congratulations are due again because you have made it past the first week. Your new employee is happy and comfortable in the new environment and ready to help make you and your business more successful. But onboarding has not ended yet, within the first 3 months (90 days), you will want to do the following

Spend some one-on-one time

Hopefully, you spent some one-on-one time during the first week when you laid out the land or during some training sessions. But as the weeks go by, one-on-one time may get scared when they get accustomed to their new role and perhaps get deep into work. Be sure to schedule a time together, it does not have to be formal, simply asking them to go for a coffee would suffice. It’s super laid back and allows you to learn more about them and how they are doing.

Invest in training

Every job role requires some sort of training. Training on company protocols and systems. Training on specific tools. And training to upgrade their current skillset. Investing in training will allow you to build an incredible company and culture. And if you were hiring on culture as I mentioned before, skills can always be learned and upgraded.

Allow for job shadowing

Job shadowing is so important. Many years ago, I was a snowboard instructor, and the one thing I found out was that people learned skills in 3 ways: 1) Reading instruction/theory, 2) Watching (shadowing), and 3) Doing. Presentations and company manuals cover the first one. Job shadowing covers number 2. And of course, when they perform the job on their own, they are learning as well. The good news is if you followed the steps, you covered everything that I learned as a snowboard instructor.

Provide a mentor

Of course, if you are the only person in the company, you automatically become the mentor. A mentor is key for any professional success. As an entrepreneur, without a mentor, your business can become stagnant, A mentor is able to see things subjectively and ask the right questions. It is essential to have a formal mentoring program set up, but it is something that you can encourage throughout the company

Build opportunities for feedback into the employees first couple of months

Build and encourage an open door policy. Every manager says they have an open door, but let’s be real here, it is very intimidating to be the new guy and want to provide feedback without feeling out of place. Build in opportunities by including them in discussions by simply asking them what they think.

Let them be themselves

You hired them for who they are, so let them be who they are. Let them bring their personality and experience to the table. As an entrepreneur, sometimes we believe that we know everything and need to instill our expectations and experience to the new person but don’t. Everyone is different so embrace that fact and trust that you brought in the right person who fits into your culture and beliefs.

Check in (more than you think you should)

During the first 3 months, be sure to check in to see how things are going.  It’s simple question like: “How’s it going?”, “All good?”, or “Anything I can do to help?”

I remember, as a young professional working for an international tech company, I would sit in my cubicle for the first few weeks, just sitting there with a question. I didn’t want to feel silly asking a very trivial question like, how do I check my voicemail, so I would wait for the next time I ran into them, But of course, my manager was super busy, so the question would sit in my notebook for a week before I had a chance to sit.

[blockquote]I would sit in my cubicle for the first few weeks, just sitting there with a question[/blockquote]

If you make it a habit to check in on them, in the morning, lunch, or at least once a day, it gives them an opportunity to get those silly, trivial questions out of the way, even though you went over it in the first week 🙂

Conduct the first review

The first interview is often overlooked by startups and small businesses that are really busy. But do NOT skip this. The first interview provides a loopback to both the employee and the manager (or yourself). It allows the employee to present their work, how they been doing, what is going well, and what is going bad.

As the manager here is your opportunity to ask them if they are happy and if they are doing what they were expected.

If you got this far with no job description and they are performing well and happy, I would consider yourself very lucky.

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