5 questions to ask before hiring your first employee

by Liam Martin
hiring your first employee

Congratulations! You’re there! Your calendar is booked solid and you’re thinking about hiring that first employee.

I know you’re probably feeling a little too overwhelmed to celebrate, but let’s take a moment to look back on everything you’ve accomplished.

You started a business working for yourself. You have a growing customer base. And you have established yourself in the market.

That’s quite a bit of work and like I said: congratulations!

But before we crack open the celebratory whiskey and wine, let’s get to the business at hand and talk about making that first hire.

The biggest hiring mistake business owners make

Most freelancers and small business owners come to the realization that they need to hire the moment they run out of time.

In desperation, the small business owner creates some idea of what they’re looking for in their minds, and posts a job description on Craigslist or asks their network of friends and family if they know anyone looking for work.

And while you can have success with this hiring strategy, you also run the risk of hiring the wrong person; costing you both time and money. Resources which I’m sure you’d rather not waste.
The rest of this article is designed for you to catch your breath on the way to world domination – or dominating your market.

Instead of jumping in and hiring your first employee, I wanted to give you a few questions to think about so you can strategically and deliberately move your business forward.

And not fall victim to the same mistake your colleagues make.

Without further ado, here are the 5 questions you should ask before hiring your first employee:

Are you happy as a freelancer?

Chances are, you started your business because you love what you do. For instance, if you’re a website developer, you probably love writing code and designing beautiful websites.

As a freelancer, that’s where you spend a lot of your time. You find clients, do the work, get paid, and the cycle starts all over again.

However, once you hire your first employee, an entire level of complexity enters your business. Your original routine of find clients, do the work, and get paid now becomes find clients, manage employee, do the work, and get paid.

In fact, Fast Company suggests that you spend six hours a week managing your employee. You will also have to develop other skills. Up until now, all you had to know was how to deliver your product or service to your clients. Now, you’ll need develop the skills required to become a good manager including effectively communication and delegation skills.

What skill set are you hiring for?

hiring employee for skill set

Once you’ve decided that you’re going to move into the realm of entrepreneurship, you need to determine what skill set you’re going to look for in your first employee.

There are a couple of ways to do this.

The first way is to determine your strengths and weaknesses as an entrepreneur. If you’re technical, but have difficulty writing, then your first employee might be someone who is a wizard with words.

Or if you’re a marketer who needs someone to help with technology, then your first hire might be a coder.

A second way to identify the skill set you should hire for is to use the 80/20 rule of time management. The 80/20 rule says that 80% of the value you add to your business is done by 20% of the tasks that you complete.

For instance, if you’re spending a lot of time scheduling meetings, jotting notes, or extracting a virus from your computer, Perry Marshall, author of the Entreprenur.com article “The 80/20 Rule of Time Management: Stop Wasting Your Time” suggests that you find a personal assistant you can pay $15 dollars an hour.

He says many businesses are killed because the business owner gets caught up in little jobs. Meanwhile, many business owners forego the work that is worth $1,000 an hour, like making a sales call, sending the right email to the right person, or negotiating a lucrative contract.

Determine which tasks are most valuable to your business and hire an assistant to complete the tasks that aren’t critical to your success.

What personality should you hire?

A recent survey shows that when it comes to hiring new employees most business owners look for personality over skill set.

In fact, a whopping 78% of business owners surveyed by the “Tomorrow’s Most Wanted” survey said that personality was the most desirable quality in an employee.

According to Richard Branson:

You can learn most jobs extremely quickly once you are thrown in the deep end. Within three months you can usually know the ins and outs of a role. If you are satisfied with the personality, then look at experience and expertise. Find people with transferable skills – you need team players who can pitch in and try their hand at all sorts of different jobs. While specialists are sometimes necessary, versatility should not be underestimated.

The only question is, what type of personality should you look hire?

As Hyper Island CEO Johanna Frelin puts it, most companies look for “people who can collaborate, adapt quickly, and are enjoyable company, but also have the drive to get things done. All those traits boil down to a personality that is essential for businesses operating in an ever-changing digital landscape. Thus, specific competence is less important.”

You might think it’s too early to start thinking about company culture, but in reality, you start building that culture with your very first hire.

Shut your eyes and picture the type of company that you want to run in 5 years. What kind of people are you surrounded by? Are they relaxed or serious? Are they the kind you want to have a drink with after work? Are they creative or are they cogs in a wheel?

Think about the kind of company you want to build and the type of people you want to build it with and begin building it one employee at a time.

How will you find your new hire?

hiring employees and where to find them
Large companies have it much easier.

They post an ad for a job on Monster.com or Career Builder or Craigslist and the resumes come pouring in. Then the human resources department sifts through the resumes, goes through an extensive interview process with each candidate before finally offering one person the job.

And if one of their new hires doesn’t work out, the company can eat the $17,000 it wasted. That’s how much a bad hire earning $50,000 a year costs a company.

Chances are you don’t have the time to sift through hundreds of resumes and sit through a dozen interviews. And I’m willing to bet you don’t have the money to just eat if the new hire doesn’t work out.

So, how can you hire talented employees without wasting time and money?

Seth Godin works with freelancers, joint venture partners, and interns for a period of months before offering them a full time job. Unlike an interview where you have an hour or two to determine if the person is right for you, you can see how the person works and if they fit the skill set that you’re looking for.

Seth boasts that he has had a 100% success rate by finding employees this way.

Why should someone work for you?

Let’s say you’ve decided to hire that first employee. You know exactly what skillset you’re looking for. You know what kind of personality you want. And you even know where to find the person.

You still need to ask yourself: Why should this person actually work for you?

Chances are their talent has provided them other opportunities, either as a freelancer or at a much more established or well-known company. It’s one of those questions you never really think about, until you’ve been turned down by potential employees.

This is your opportunity to differentiate yourself.

For instance, let’s say that you need to hire a software developer. Unlike a freelancer who has to get involved in marketing, taxes, invoicing and a whole host of other administrative work, you can promise your software developer that he doesn’t need to worry about any of those tasks because you’ll do it for him.

And unlike in a larger company where bureaucracy governs, your software developer can work in a stress free environment continuously pushing code and using his imagination to create new features for your product.


Hiring the first employee is going to be one of the most important decisions you can make. So before you rush into anything, make sure you’re able to answer these five questions.

Now, break out that drink and raise toast to yourself. You’ve made it this far, and with a little bit of strategic thinking, you’ll create the company of your dreams.

And complete your quest of world domination.

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