How to succeed as an IT contractor

Last Updated on January 23, 2022 by Dave Farquhar

I met a young IT contractor a little while back. His talent was sky high. So was his potential. And his rawness. It’s not my place to go into great detail about that rawness, but one thing I noticed about him was that he had a very self-defeating attitude about him. It shouldn’t have been hard for him to succeed as an IT contractor, but he was his own worst enemy.

Several times he started a statement with, “If I don’t get fired,” or something to that effect.

It occurs to me that perhaps my experience as a contractor would be helpful.

The most important thing is to know what they expect of you, and do it. Contractors generally come in with a very specific assignment, especially in a large company, so the key to thriving is to know that assignment. In this guy’s case, that assignment was two things. He was very capable of doing those two things. In fact, the assignment was well beneath his abilities.

But that’s fine. They don’t grade a contractor on how much of his or her potential he or she is using. They grade on how well he or she carries out the assignment. Everywhere I’ve been, any time I’ve shown any flashes of unused potential as a contractor, some additional work found its way to me. Sometimes it happened that day and sometimes it happened more slowly, but that’s OK.

Many companies use contractors as a way to try out talent before offering a full-time, permanent gig. That’s called right to hire. Not every shop does it, but many do.

That’s why it’s important to carry out orders. Talent is one thing, but the ability to stay on task and in bounds is also important. A person with run-of-the-mill abilities who follows directions reliably can have a very long career.

That’s why “if I don’t get fired” was a curious statement. He had two easy assignments. Any day he came to work sharp and well-rested, he would have been perfectly capable of crushing those two assignments. He probably could had shown up for work drunk a couple of times a week and still done the work capably, not that I would have recommended that.

I was in a position to know. I’ve done both of those assignments he was getting. When the senior director was walking him around introducing him to people, he introduced me to him as the guy who could help him more than anyone else. Then he temporarily sat him in a cubicle near me. The senior director didn’t tell me to help him. He didn’t need to.

Perhaps not coincidentally, the other two people closest to him got their start in the company as contractors just like I did.

I had a history as a contractor. My worst contacting gig lasted about six months, a very long time ago. To be honest, the corporate culture there wasn’t the best fit for me, certainly not at the time, and the job was a bit beneath my abilities. Not as far as my new acquaintance’s gig was, but it was a step down in responsibility from anything I’d had in a good while.

They terminated my contract after about five months. It was a financial decision. But then they kept me on for almost an extra month because my soon-to-be-former coworkers kept missing work for personal reasons. I didn’t pry; the extra time to find a new gig meant I didn’t have to just take the first opening I could find. Here’s the important thing: They may or may not have liked me, but they trusted me enough to keep me along as a lame duck for a few weeks.

In the meantime I was applying for every internal job opening they had and wasn’t getting callbacks. It frustrated me, but I kept showing up for work and doing my job.

I applied those lessons to my most recent gig as a contractor. This time the work suited me but it was temporary. Again, I applied like crazy for internal openings, and I got interviews this time, but became a perpetual runner-up. Again it frustrated me, but I kept showing up for work and doing my job, and when I interviewed outside the company I was discrete about it. Then one day, someone who wasn’t my boss requested a closed-door meeting with me. The department had an opening for a security architect. He had a threat and vulnerability analyst who wanted to be an architect. He asked if I wanted her job. The more he told me about the job, the more I liked it. A few weeks later, they hired me as a security architect and swapped our job titles.

My first review was stellar. I don’t think it was much of a surprise. After watching me work a few months on their centralized logging project, they knew what they had.

That’s the thing about being a contractor. Being a contractor lets management observe talent in the workplace. You find out a lot more by working with someone for a few months than you do from an hourlong interview.

Sadly, this particular contractor didn’t make it. I wasn’t the only one who told him to stay in scope and on task, do those two things well, and wait for increased responsibility and an eventual job offer.

He made several mistakes but I think the biggest problem was that he tried far too hard. We have a cliche at work about trying to boil the ocean, and that cliche seemed made for him. He jumped in too fast, didn’t put what he was seeing into context, asked far too few questions, and made too many people uncomfortable. It turned into a vicious downward spiral of self-defeating behavior.

And then it was over as quickly as it started. Well, over for him at least.