Interviewing Your First Employee

Interviewing your first employee can be both as exciting as it is nerve-racking.

As the interviewer it is important to be calm and collected, more often than not your interviewee is going to be nervous; nothing is more awkward than both sides being noticeably nervous! I still remember hiring my first employee, it was awkward, I didn’t know what to ask, and I didn’t know what to look for. Fast forward a few years and now I have some experience under my belt and learned from my mistakes. Now, I don’t have to hire as much because the people I do hire tend to work well in the position, proving that the interview process is working.

After all, the whole point of the interview is to make sure that, not only the person will fit the position well, but that the position will fit the person just as well. A happy worker is a good worker, and good workers tend to stick around longer.

Now, we could go with the standard, run-of-the-mill interview questions, you know the ones..

  1. How Did You Hear About This Position?
  2. Why Do You Want to Work at This Company?
  3. Why Should We Hire You?
  4. What Are Your Greatest Strengths?
  5. What Do You Consider to Be Your Weaknesses?
  6. Tell Me About a Challenge or Conflict You’ve Faced at Work.
  7. Tell Me About a Time You Demonstrated Leadership Skills.
  8. What’s a Time You Disagreed With a Decision That Was Made at Work?
  9. Tell Me About a Time You Made a Mistake.
  10. How Would Your Coworkers Describe You?

Don’t be this type of interviewer, especially when Interviewing your first employee.

Honestly, these questions won’t help as much as you might think they will. When you interview multiple people with these questions you start hearing very similar answers, and chances of someone really sticking out among the crowd decrease. On top of it, chances are they went online and looked up how to answer these questions while sounding the best.

Rather than being this generic, get them really talking. It is always best to think of your interviews as less of an “interview” and more of a 1-1 conversation with a complete stranger. You just want to know them more; I don’t really care that they made “top customer service at Company ABC” because I don’t know what Company ABC’s standards are.

The immediate goal should be to ease their nerves and get them comfortable talking to you,  if they are nervous they will still have their walls up. Just like in sales, you have to break down that initial defensive barrier to really see the prospect. People love talking about themselves, if you can get them talking about a hobby or interest they enjoy, you got your way in. This is why I personally don’t follow any specific “list” of questions. Study your prospect, can you see any tattoos, are they wearing any unique jewelry or fashion items? Point them out and see if they open up about it.

More importantly, it’s not what their answers are, but rather how they answered the question.

Once again, I want them comfortable talking to me. If their eyes brighten up, the chin is held high, talking with confidence they are in their comfort zone. From there you can dig in deeper, and start talking shop. That’s when you start describing the position, responsibilities, company structure, etc.. While you’re doing this, you are still keeping a keen eye on body language. If they stay confident and comfortable you know they can handle everything you’re describing. If they start to shut down and shell back up, something got to them. That subtle change in nature can tell you a lot about their future at the company.


If I know that I will be their immediate manager I need to make sure that the interviewee and myself will get along above all else. If there is chemistry, then I can mold them to be the employee they need to be to fill the position. However, if I sense that I am going to be butting heads at every turn, I already know it won’t work in the long run.   This brings me to another good point, if you are not going to be their immediate manager, you should not be the primary interviewer. Always make sure the person spending the most time overseeing that prospective employee is the one taking the lead.

To sum up, When your Interviewing your first employee, just have a simple conversation.

Just have a simple conversation,  not an interview. Aim to leave an interview making a new friend, if I feel like I haven’t done that I know the prospect probably won’t be the right choice. This is especially true for businesses with small teams; odds are you will be a very close-knit group and with time, may even feel like family. This is the type of employee culture that pulls customers in and enhances the customer experience.

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