September 9, 2016

Tips for Hiring Your First Employee and Growing Your Team

BY John Paul Narowski IN Small Business, Small Business Learning 0 Comment

Growing Your Team

The early stages of growth in a company can feel a lot like riding a bike blind – you’re going fast, need help steering, and might faceplant into a pole at any point.

Going from a solo operation to a team is infinitely more complex than going from 100 to 101. Hiring slouches early on is downright ruinous, while getting it right … (singing) the clouds part as light pours onto your paper-steeped desk.

Your first new hire is an integral “can’t-live-without” cog in your growth machine, your #2. (The same goes for #3 and #4.) Your very sanity depends on it. It’s VERY expensive to get this wrong. Trust me, I have.

I’m not going to lie, hiring is tough. The entire process is lengthy, and you never really know if you’ve found “the one.” Even knowing when the right time to hire is a challenge.

Here are a few things to consider.

When is the right time

It’s easy to look at your revenue and think “I can’t afford anyone else.” Early expansion can be painful, but it’s like starting a family – once you’ve done it, you can’t imagine how you lived without them.

Many entrepreneurs make the mistake of trying to do everything themselves. I mean EVERYTHING. You are actually losing money by doing this, no question. Sure, as the owner of a small company, you’ll wear a lot of hats. But you don’t have to wear every hat. Balancing 30,000 things on your head might be a cool Cirque du Soleil trick, but it’s a major drawback in running a small business.

Side note: If you ever want to consider selling your company, the superhero “nobody-can-do-it-better” founder is a huge deal breaker. You need to show robustness and distributed dependence on more than one person.

How I decide to hire (and whom)

To decide if I need to hire someone, I start by valuing my time at an hourly rate, based on what I could get working for someone else. Then, I look at all of the tasks that I consider outside of my core competency. Since I’m a developer, I look at things like how much time I’m spending on admin, bookkeeping, and customer support.

Then, I consider the potential upside. If I was able to focus more on the thing I do best – coding – could I positively affect growth? If the answer is yes, then I hire.

The single most important hire I’ve ever made was my customer success person, Shirley Robinson. She has a magical knack for solving problems and a deep, genuine care for our customers. She has a patience and disposition that I could only dream of.

I started karmaCRM doing both development and support, but quickly realized that by focusing on one the other suffered. Shirley solved that and has quickly become a cornerstone of my company’s foundation.

Think what would have happened if I had tried to save money and keep doing it myself. I’d be swamp wading through support requests, doing a mediocre job, while watching my product slowly die.

Before you hop over to post a job on Craigslist, take some time to really think about what type of person you want. Not their skills but their essence. Are you hiring a superstar “ninja” with an ego the size of a hot air balloon, or do you want someone with humility, energy, and hunger to learn?

At this stage, experience matters a whole lot less than essence and raw talent.

Hiring for experience or talent

The first step is deciding what you’re looking for – raw talent or specific skills. They both have a place, but personally I’ve had much better luck hiring for raw talent instead of a specific skillset.

What I mean when I say “raw talent” is that the person you are hiring is intelligent, capable of learning fast, and is hungry to learn. They might not have done the specific job before, but because they have talent, they can learn fast.

They’re clay, waiting to be sculpted (and excited about it).

I’ve hired “seasoned” employees before, and let me tell ya, they come with a lot of baggage. I once hired a 100k senior project manager who professed his “cold lunch” project management style. This meant he kept people so busy that they didn’t have time to eat their lunch warm.

The first week, he took two-hour lunches every day and was caught reading a magazine at his desk multiple times.

He came with a jaded, enterprise-entrenched sense of work ethic. While this may have worked at Acme Corp X with a billion employees, it certainly wasn’t going to cut it in my team of 5.

Sometimes the seasoning is too strong and the food is best with just a little salt and pepper.

People with raw talent are hungry and moldable. They are also inherently versatile and can help fill a lot of cracks. I typically seek out people who are comfortable being “thrown in the fire” instead of those who expect manuals and procedures.

Let’s be honest, if you’re anything like I was, you have no employee handbook, your processes are scribbled on napkins, and you need a firefighter, not a gas station attendant for your #2 hire.

Know thyself

With every new hire, we have everyone on our team do a personality test. This helps us understand our current dynamic and how the new hire might fit in. Culture cannot be an afterthought while growing your team, and investing in understanding what makes each person tick can be paramount to getting stuff done.

We took the free version of the Myers-Briggs test (but there are plenty of other options out there) and analyzed the results. Then we discussed our results as a team. We were sure to highlight aspects of the results that were accurate, and others that were not.

These tests have some very useful insights, but it’s important not to put yourself in a box. Personality tests can help you understand the current dynamics powering your decisions, but since you’re dynamic, so are your results. My long-term team members and I have taken the test multiple times, and our results have changed over time.

How powerful it is to work, change, and grow with others.

Ok, so now you know what you’re looking for and you have a solid understanding of your team’s genetic makeup. Now it’s time to decide what this new hire looks like. Is it an individual, a group of people, or a robot? Are they sitting next to you, or across the ocean?

These days, you’ve got options!

Consider contracting instead of hiring

As a bootstrapped small business owner, you learn to think outside of the box. Does it need to be a real-deal W-2 employee, or could it be a 1099 contractor? Does it even need to be one person, or would the job be done better by a few part-time people.

Don’t pigeonhole yourself when making this huge hiring leap. I’ve had businesses run entirely on a crew of contractors, hired mostly from sites like It’s affordable, and you can hire much better talent when location isn’t as important.

This can’t work for every company, but it’s important to at least consider a contractor instead of an employee, especially to start. They are less expensive from a tax perspective, and you can do a contract-to-hire, giving you a trial period with the person.

Please consult your lawyer and HR person before pulling the trigger. The contractor vs. employee lines can be quite blurry.

Once you make this determination, you’re off to the races to write your shiny new job posting. DON’T SKIMP on this part. If you write a zombie-inspired job description, you’re going to get zombie applicants. Spend the time and write a zingy job application that has personality. You’re fighting for the smartest, most versatile people. Show them why they should pick you.

So with the post up, how do you actually go about the hiring process. Everyone probably has their own opinions here, but we’ve shared a peek into our process for your enjoyment.


Hiring is a daunting, yet rewarding, process, but don’t rush it! Budget some time for a little introspection. What do things look like right now, what’s your culture like, what are you like? Each hire will make a resounding and definitive stamp on your company’s culture, so it’s best to be intentional. Otherwise, your culture will grow wild like weeds.

It’s almost a guarantee that while growing, the vision you have for your company will get foggy. I’ve found it a very healthy practice to do a personal retreat at least once a year and make sure my “why” is secret-island-mountain-spring clear.

Continuously revisit your passion, and course correct when necessary. If you do, it will be easier to identify who you need alongside you to actualize your vision.

I’ve been hacking at various business ideas since I was 16. I’m a full stack developer and love crafting user experiences. I’ve been nose deep in code since I put the legos down, and built several successful businesses in the process. I’ve lost some hair, gained some experience and throughly enjoyed the journey.

Schedule a demo today... Find out why so many customers love us !

Schedule a demo
  Get expert sales tips straight to your inbox, and become a better salesperson. Subscribe to the Sales Blog below.