hiring experience


Hiring is such an important part of running a business.  Getting the much-needed people and skills to help you grow your business is crucial in meeting your business’ goals.

While most of us would love to have a high batting average, the reality is, things don’t always turn out the way we expect them.  Whether you like it or not, you’re going to have your share of bad hires.

This is, of course, part of an entrepreneur’s life. Even the most successful companies have experienced hiring the wrong people.  As long as you learn from these mistakes, getting the right talent shouldn’t be far behind.

This is exactly what FreeeUp co-founders Connor Gillivan and Nathan Hirsch went through before they started FreeeUp.  After several bad hires, they’re now running one of the most sought-after freelance markets today.


Their Story

worst hiring experience

Connor and Nathan’s partnership go far back.  From college buddies, they became business partners after starting their own Amazon business in 2008.

At a time when courses, gurus, and software weren’t a thing yet, they were pretty much doing everything manually back then.  From product sourcing and repricing to listing optimization, they definitely had their hands full.

Like any other business owner, however, there comes a time when changes need to be made.  Doing everything manually was just becoming too overwhelming, not to mention their desire to take the business to the next level.

With all of these considerations in mind, they decided to begin automating tasks.  To make this happen, however, they’ll be needing the help of a competent developer.

This would have been easier if they had knowledge of automation and development.  Unfortunately, they didn’t know much about it at that time so they did weeks of research to get it right.

Along with this tedious task of doing research, Nate and Connor also began looking for the answers to the following questions:

  • How much would hiring a developer cost?
  • What programming language should the software be built on?
  • Where can we find a good developer?


The Hiring Process

worst hiring experience

After weeks of brainstorming, Nate and Connor decided to use Python as their programming language of choice.  They also began posting projects on freelance market sites and received hundreds of applications in return.

It was an exciting yet exhausting time, to say the least.  They reviewed countless resumes and interviewed one freelancer after another.  Despite all their efforts, however, they were still not sure who to hire after spending weeks interviewing people.

It was a disappointing time as one may think.  Just when all hope is lost though, they finally got the break they were looking for when a freelancer they worked with sent a referral.

The candidate was someone this freelancer worked with previously in another platform and from all indications, he seemed to be a good fit. He had great spoken English, understood Amazon and his rate was affordable.

The freelancer basically had everything they needed based on his credentials.  He looked even more perfect for the role after they had the chance to interview him which went pretty well.

From all indications, this was their guy.  He was the one they were looking for after weeks of searching so they formally hired him so the project can finally commence.


The Project Kicks Off 

worst hiring experience

Having found the right freelancer for the role after weeks of searching, Nate and Connor have finally got the project started.  Though they are, at that time, already months behind, they still took the time to get everything organized.

The group spent an entire week putting together an outline of all the things they needed the developer to build.  It’s important to be clear about everything before jumping in the water so the extra week was completely necessary.

After a week of creating an outline, they spent another week talking it through with the freelance developer.  They wanted to make sure that they set the expectations right and that they can answer any question the developer may have before they begin.

With everything ironed out, they took a much needed weekend break and scheduled project kickoff the following Monday, 9 AM. They can finally begin the software development project…or so they thought.


Missing in Action

worst hiring experience

As can be expected, everyone was excited when Monday came around and who can blame them?  They’ve been talking about building a software for years.  After spending months preparing and finding the right person, their vision is now within reach.

As 9 AM came, however, the freelancer was nowhere to be found. They waited till noon but the freelance developer never showed up.  He totally went MIA (Missing in Action) to everyone’s utter disappointment.

They tried reaching out to the person who referred this freelancer but he too was nowhere to be found.  Sadly, they’ve never heard from either freelancer again.

Disappointed doesn’t even begin to describe what everyone felt after this giant mess.  Thinking about the months they spent planning everything and finding the right person is just too upsetting.

What’s great about Nate and Connor is that they understood that it’s part of running a business.  There were definitely a lot of lessons learned from this experience and below are some of them:


Begin with smaller projects

worst hiring experience

One of the biggest takeaways from this hiring experience is the importance of taking baby steps.  Hiring a developer to create software and automate is quite a huge step.

There’s a lot that hangs in the balance when you designate something as big as this to a freelancer.  One of the first adjustments they made to avoid the same mistake is to outsource smaller projects instead.

They hired freelancers to do their product listings and customer service on their behalf thereby lightening their respective loads.  Doing this allowed them to stick to their manual approach with getting overwhelmed now that they have extra hands on deck.

This move also gave them peace of mind because there was less impact on the business even if the freelancer didn’t show up.  They’d still be there should the same hiring experience happen again only this time, they’re not overly reliant on one person.

As a business owner, you’d like everything to still be in place should a similar incident happen again.  It’s critical for the business to continue its operations despite possible disruptions.  Outsourcing small projects, in the beginning, will definitely give you that leverage.


Build Trust

worst hiring experience

One of the things Nate felt they failed to do that led to the unfortunate hiring experience was that they didn’t take the time to build trust.

While they did spend time talking to the freelancer about the details of the project, they weren’t really able to build trust the way they were supposed to.  They relied on the recommendation of a freelancer they worked with and on the resume of the person being referred.

What they failed to accomplish was to really get to know the person first and establish rapport.  Let’s face it, the guy was completely unknown but his credentials were too good to pass up.  He was technically hired for his skills and there was less focus on his attitude.

A lot of business owners tend to commit that mistake too.  It’s hard to pass up talent when you see one especially if they fit your requirements to a tee.  The best way to avoid falling into this trap is to give the freelancer a test project.  A rather small one just so you can get a feel of what his or her process is and how committed he or she is in completing the project on time.

Doing this will give you a better idea if the freelancer you hired possesses the work ethic you would love to have on your fold.  If he or she manages to meet your expectations on this small project, chances are, he will be able to do it with bigger ones.


Organize the interview process

worst hiring experience

Communication played a huge role in Nate and Connor’s bad hiring experience.  Looking back, they felt that they focused too much on skills during the interviews.  They didn’t pay much attention to attitude and communication which are equally important when working with freelancers.


As a business owner, it’s natural to focus on skills because you want someone who can deliver what you require but paying attention to attitude is also essential.  What good would it be to have someone competent if that individual doesn’t know how to follow the rules?

A good attitude goes a long way because it makes working together much easier.  There’s no better way for a group to function as a unit than through harmony and teamwork.  If you really want to take your business to the next level, hiring for attitude is something you should practice.


worst hiring experience

Getting a feel of how good a freelancer communicates reduces the chances of a bad hiring experience.  Is he or she easily reachable?  Does he or she only work on a specific time of the day?  How long do they respond to emails or chat messages?

It’s important to get the answers to these questions as early as possible because a lot of things depend on it.  You have to remember that you’re dealing with a remote freelancer who may not share the same timezone and availability.

Since your means of communication are all online, you want to make sure that this will not present any problems.  Any breakdown in communication can be catastrophic for any business.  You stand to lose a lot of money and time if you can’t establish this right from the beginning.

By asking these questions and emphasizing their importance during the interview, you would at least get a picture of how it would be like to work with them.  If you have to compromise a lot just to get in touch with them, then it may not be worth hiring them in the first place.



worst hiring experience

It’s always good to have a Plan B in case Plan A fizzles which is exactly why you should diversify freelancers across your business.  Leaving everything up to one person may be more affordable but if that person bolts or decides not to show up, you’re doomed.  It’s a bad hiring experience waiting to happen.

Just like what we mentioned earlier about starting with small projects, having more freelancers gives you a great safety net.  By distributing the work among a number of people, you’re keeping your business protected because you have backups in place.

It may cost you a bit more to hire more people but it won’t cost you as much if someone leaves and no one’s there to take over.  You have to think in advance and anticipate possible scenarios.

What if the freelancer gets sick or goes AWOL?  Do you have other people who can take over?  What happens if the work is left undone?  How much do you stand to lose if work is left unattended?

You wouldn’t have to worry about these things if you have enough freelancers on your roster who knows what each other does.  While there may be a few exceptions because of the specificity of the skill, it would be in your best interest to always get backups for everyone.


Final Thoughts

Failure may be a difficult pill to swallow but the lessons they leave us with will continue to serve us for years to come.  A bad hiring experience is inevitable.  Every business has had its share of hiring horror stories.  What separates the successful ones is their ability to adjust and learn from those hiring experiences.

If you are in the same boat as Nate and Connor, then congratulations!  You can now retrace your steps and identify what went wrong so you can make it right the next time.  You now have the luxury of making adjustments to avoid a similar hiring experience in the future.

If you belong to the lucky ones who hasn’t had a bad hiring experience, then kudos to you.  Keep doing what you’ve been doing but take note of the suggestions we provided above.  You’ll never know when you might need them.

If you loved the suggestions provided in this article and find them useful, please don’t forget to share them on social media.  We’d really appreciate it.


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