Hiring Your First Employee: 4 Factors to Consider

I had just walked the candidate to the door, as he said goodbye to the rest of the team. As I sat back into my chair, I looked at everyone else. Should he be our next hire? Two people gave a resounding yes. One other gave an equally forceful no. And suddenly, we had a heated discussion on our hands.

How could you not like this guy? He’s the best person we’re going to find!

I couldn’t help but add in my two cents as well to the discussion. But honestly, I couldn’t help but notice that for some reason, I was also having doubts…

One of the hardest things to do as a manager is hire the right employees. I would even say it’s more difficult than even finding funds to pay for the employees. This is because suddenly you are required to possess all of these new skills: how to be a manager; how to discern culture; how to ask the right questions; and finally, how to be a cheerleader about your company to someone you’re not convinced you want yet. On top of all of these things, you must also continue to run your new, young business.

There has been a great deal written about hiring great employees. Much of it is likely spot on. However, I’ve found that much of it is also not grounded in the reality of a bootstrapping startup. You may have heard the same type of advice:

“Only hire people who are smarter than you!”

“Hire slow and fire fast!”

This type of advice may be good for Facebook, but it’s not particularly well-suited for you. If your potential employees are good, they are just as wary of choosing you as you are choosing them. After all, at this point you are likely not profitable, you probably can’t pay much, and you could still be in the phase where it’s undetermined if you are going to be successful. So taking an extended period of time with a prospective is an almost sure-fire way to keep them from working for you.

Here are my tips for hiring new employees as a bootstrapped startup:

(1) Determine the 5-year plan for this applicant – Do you even need an employee right now, or would a contractor suffice? It may be simple to consider that there is a ton of work at the moment, but what happens 6months to 1 year down the line? Plan out this potential employee’s role, and make sure that there is a long-term strategy for that person.

(2) Make sure the applicant is passionate about your company – you will be requiring him/her to work long hours for pay that probably isn’t that impressive. You don’t just want someone searching for any job. You want someone who strongly believes in what you are doing and wants to contribute to that greater goal.

(3) Find a go-getter – Of course it is important for your applicant to have a great skillset. But remember there are a lot of things that can be taught. What I’ve noticed cannot be taught is how to be ferocious. You want someone who doesn’t tire easily, someone who will constantly look for new pathways, someone who doesn’t need to be hand-held and someone who makes it their personal mission to get the job done. These characteristics are much more important. Why? Because more likely than not, they will be doing many things not in the original job description, and you will likely not be doing the best job of managing them to start with. So you want someone who will take their role and run with it.

(4) Suggest a 30-day “cool-off” period – Startups aren’t for everyone. Sometimes it is you who find that out, and sometimes it is your employee. The worst thing you want is someone who is detrimental to your culture, because it turns out that they hate working here. So suggest a 30-day period to assess how things are going. After that, you will feel more confident about a full-on contract.

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