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Tech Business Hiring Horror Stories (and How to Avoid Them)

Tech Business Hiring Horror Stories (and How to Avoid Them)

Thursday, August 18, 2016/Categories: hiring-and-human-resources

When you find a tech contractor who is a good fit for your IT business, they can be worth their weight in gold. Okay, maybe not literally, but the right contractor can be pretty darn useful in helping you get the job done faster than you could yourself.

But when you hire a contractor who doesn’t work out because they don’t have the appropriate technical skills or they are a bad fit, it can be a disaster. Two IT business owners share their personal tech contractor hiring horror stories with us and tips so you can avoid the same fate.

The Case of the Under-Qualified Web Developer

Nathan O’Leary (@oleary), founder and CEO of (@MainelySEO), says he brought on a contractor to help his business with a website development bottleneck. However, O'Leary soon discovered the person he hired to code the sites didn’t have the technical skills they had claimed to possess.

“Coding websites is a lot of work, so this person was brought on to help get through some projects that we were on deadline for,” says O’Leary. “They misrepresented the skills they said they had. It took me several weeks to figure that out because I was not reviewing their work as closely as I should have. Because I trusted them, I just was hoping that they would be able to hit the ground running. Instead, it ended up creating more work for everybody because they were breaking things and they weren’t able to complete the projects in a timely manner.”

O’Leary says he typically hires contractors based on referrals from friends or other business associates, or by posting ads on Craigslist or freelancer websites like Upwork. In this case, he hired the relative of an employee based solely on their recommendation – something he says he won’t do again in the future.

The lesson learned: “If I had checked their references or checked their work, then I probably wouldn’t have been in this situation. I probably wouldn’t have hired them to begin with,” says O’Leary. “The learning experience from this is: don’t hire someone’s friend or family member.”

The Mystery of the Developer More Interested in Solving a Rubik’s Cube than Customer Problems

Bryan Clayton (@bryanMclayton), CEO of (@YourGreenPal), a website and mobile app that connects homeowners with lawn care experts, needed help creating his business’s app back in 2013. Clayton says he and his partners put in significant time interviewing and vetting potential developers.

“We finally landed on a guy that had a nice-looking website featuring mobile apps he had built for other people in town,” says Clayton. “He came recommended and his price was in our budget, but in the end, it didn’t work out.”

The problem? The developer created an app that was functional, but clearly not designed with the end user in mind.

“It worked, but it was just so damn hard to use,” says Clayton. “We got a system that literally would take you half an hour to figure out how to use. If you had 100 people use it, only five would get through it.”

Unfortunately when he and his team tried to provide feedback to the developer, they got nowhere.

“It was just so painful to get him to make tweaks and changes because he was so close to the way he had designed the system,” says Clayton. “Any changes, any deviation from the way he laid it out, he would get very defensive about. He was just was not open to feedback.”

Clayton says he can point to one particular meeting when he knew it was time to walk away.

“I knew the relationship had reached the point of no return when we were in a meeting with him about some changes to the user interface and while we were talking, he was solving a Rubik’s Cube,” says Clayton. “That’s when I realized, ‘We messed up.’ In the end we had to scrap the whole thing. It was a total waste of six months and $70,000. It was a nightmare.”

The solution? “The second time around, we built it ourselves,” says Clayton. “We literally taught ourselves programming as we built it.”

The lesson learned: Clayton said he realized from his bad experience with the contractor that what they should have done in the first place was hire one person with the skills to design the look and feel of the app and a second contractor with the skills to handle the back-end coding. 

“My advice is to work with a user experience designer first and create a prototype for your product before engaging a developer to build it,” says Clayton. “This was a lesson we had to learn the hard way.”

4 IT Contractor Red Flags

Even if you carefully vet your contractors, you never know exactly what you're going to get until the project starts. However, these red flags may be a good indication that you should run far, far away. Be wary if a tech contractor…

  • Is late for an interview or misses it altogether.
  • Won't provide any references.
  • Gets the details of an assignment wrong.
  • Responds to feedback with arguments.

For more tips on hiring contractors you actually want to work with, read “Hiring Freelancers / Contractors? Do These 5 Things First.”

About the Contributors

Bryan Clayton

Bryan Clayton is a serial entrepreneur. He founded a landscape construction company Peach Tree Landscaping in Nashville, Tennessee, and grew it to more than 125 employees before being acquired.  Currently, he is CEO of GreenPal, an online marketplace connecting homeowners with lawn care professionals in their town via the web and a mobile app – kind of like Uber for lawn care.

Nathan O'Leary

Nathan O’Leary started Mainely SEO in 2010, and has been helping local Maine businesses utilize search engine marketing and social media to reach new customers for over six years. He is also the founder of, a website and social media channel that has over 40,000 followers to date. Being an entrepreneur and digital marketing expert, he understands the ins and outs of running a business and how to strategically market a company's particular strengths online.

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