Hiring Your First Employee For Your Service Business

Firstly, congratulations. You’re busting out of the single person box, and you’re taking the first steps towards a much larger and more sustainable business.

Hiring employees is something that gets easier over time. It’s a skill that needs to be practised. Don’t expect to get everything right your first time around.

I’ll try to give you some guidelines to help you along your way.

Vision Over Job Description

You need to write out a basic job description, but it’s better to spend more time describing and discussing your company vision. For your potential team member, it’s interesting to hear something like:

“Our goal is affordable legal advice for people being sued by large corporations. We want to be the lifeline for people who have no options left.”

Compared to:

“You’ll be doing word processing, running errands, and filling out expense reports.”

Since your first employee’s job description will inevitably change or move beyond what you will initially wrote down, it’s more effective for them to feel a part of a larger vision and goal. Because as the first employee of your company, they are a vital part of the vision and goal.

This also serves to eliminate the “thats not my job,” mode of thinking, which is the kiss of death within a small company.

Go With Your Gut

Even if all the boxes are ticked, their experience is perfect, and they seem perfect for the job, do a gut-check. If something feels a little bit off, or weird: do not hire.

At the very, very least, put them on an hourly contract for a few weeks so you can see them in action before you offer a full-time employment contract.

You have a library of subconscious indicators detailing habits, body language and facial ticks that untrustworthy people exhibit. You may not even be aware of these indicators, however it will manifest as a subtle feeling of unease about the candidate.

If something is setting off your ‘spidey sense’, proceed with extreme caution. Without exception, every time I deviated from this path, it’s ended up costing me tens of thousands of dollars, and I ended up regretting it.

Always do a gut check, and always listen to your gut.

Personality/Cultural Fit

Personality clashes are a very real issue in small teams. You’re going to be working together closely for extended periods of time, often under pressure. You need to make sure any personality conflicts are discovered during the interview process, rather than 2 months into the job. This is in both of your interests.

It’s a good idea to consider the ‘Drink Test’. Which is, simply, if you had a free night, would you choose to have a coffee/drink with this person?

Now, any job-hunter worth their salt is going to come prepared with stock answers to stock questions, and that is going to cause interference with your personality evaluation mechanisms.

The tricky part, is talking with the candidate enough to get an answer to the Drink Test. This is why you need to get off script, and ask a range of questions where people will not have prepared answers so you can get a better understanding of their personality.

Cheat Sheet – Tried and Tested Interview Questions

At the risk of making my own interviews harder, here is a list of questions that have been very helpful and successful for me.

  • Please describe a time you were angry at work, and how you dealt with it.
    • This question gives you a wide range of information about what makes someone angry, and how they deal with and resolve conflict.
  • What would your last boss say are your strengths?
    • “What are your strengths?” is a typical, standard question. However this question flips the script and encourages people critically examine themselves from someone else’s perspective.
  • What would your last boss say are your weaknesses?
  • What was the biggest problem at your last job?
  • Could you tell me about a time you had a serious argument with someone at work, and how it was resolved?
  • What books are you reading right now?
  • Can you tell me about a time you went above and beyond the call of duty at work?
  • Could you tell me about your experience in customer service?
    • Intentionally broad to allow someone to give you their concept of customer service, and allow you to compare it to your own.
  • Can you tell me about a situation where you had a difficult moral decision at work, and how you handled it?

These questions are designed to help you get a feel for someones personality and conflict resolution skills.

All Systems Are Go

If you’ve gone through these questions and you’re smiling and nodding your head at the answers, you’d be happy to go for a drink with them, and your gut is clear, then you’re ready to make your first hire. Good luck!

What were your challenges in making your first hires?

Jay Winder

Jay Winder is the Australian Co-Founder of MakeLeaps. Jason came to Japan in 2001 to study martial arts, set up his first business called Webnet IT in 2003, and set up MakeLeaps in 2010 with the vision of unlocking the potential of freelancers and businesses in Japan with clean and powerful software. If you like, follow me on Twitter.

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This article has 2 comments

  1. I found my first employee by asking myself 'Where would I look for work if I was on the market?' The job I was advertising was junior but fairly technical, so I ended up placing a local advert on Craigslist and had an informal Starbucks interview with a guy who responded. He has now worked for us for nearly 2 years and has fitted right in to the role.

    I offered a basic salary plus 10% of any income generated by the employee. This has worked out well for us both as he is actively seeking work for the company as he is rewarded.

  2. Wonderful stuff. I always adopt “spidey sense” myself, and (when I've listened to it) it's never lead me astray.