Tech & Work

Need extra help on projects? Follow these rules when interviewing contractors

The success of a project often hinges on your ability to bring in good contractors to perform some of the work. Use these tips when you're interviewing candidates to ensure that you're getting the best talent for your money.


The goal of any interview is for the interviewer and the applicant to engage in a two-way information exchange to assure each other that the job will get done properly at a fair price. But if you’re bringing on contractors to help complete a project, interviewing them requires a different approach than interviewing a candidate for a permanent job.

In this article, I’ll offer tips on conducting successful interviews to help you hire the most qualified contractor for your project.

Figure out what you want
Although it sounds obvious, before you can hire the right contractor, you must first figure out what you want done: What is the project goal and how should it be completed? Many of the clients I’ve interviewed with either didn’t have a clear idea what they needed or told me they thought they needed one thing, when the actual project ended up being completely different.

Write a detailed job description that you’ll be able to present to the contractor. In the process, you’ll figure out what critical experience the contractor must have and an appropriate pay range for those skills. For example, in addition to computer know-how, does the job you need accomplished require:
  • A permanent employee or a contractor?
  • A generalist or a specialist?
  • Someone who can manage people, work as part of a team, or work alone?
  • A creative thinker—someone who can take the project in new directions—or someone more suited for following directions?
  • Someone who can deliver on a fixed timeline or be flexible enough to accommodate changing deadlines?
  • A person who can switch between tasks or who can focus on one subject for a long time?

Streamline the interview process
Don’t subject a contractor candidate to interviews with everyone from new hires to upper management, a process that can drag on for several weeks. If it takes you weeks to deliberate, you might end up losing a great candidate for the position.

Limit your interviews to two per candidate. And make an offer as soon as you can. Not many contractors can afford to wait weeks and weeks while you make up your mind.

Keep in mind that just as you judge a candidate on an interview, he or she is also deciding whether to take on your company. A disorganized or haphazard approach to interviewing will raise red flags for an experienced contractor. As for multiple interviews, I’ve heard of some contractors who, after being pumped for information again and again, have put their foot down and said, “Sure, I’ll come in again. But I’ll be charging by the hour from now on.”

Make those one or two interviews count
Having only one or two interviews with a candidate makes it all the more important to make the most of that time and take every opportunity to find out more about them.

First, make sure to ask contractors to bring samples of their work to the interview (a prepared candidate will do so without prompting). Also, consider presenting a brief and simple test for the work the contractor will be doing. Make sure that it’s fair, though—don’t spring something entirely new on the candidate. And you shouldn’t ask them to produce something you’ll use—anyone would take offense at being asked to work for free. If you must use anything produced in an interview, notify the candidate up front and make arrangements for compensation.

Listen to the contractor’s vocabulary: Does he or she know and use the terms used in your business? Does he or she use acronyms or give other indicators of familiarity? Here are some questions you can ask to dig deeper into a contractor’s qualifications:
  • If you must have someone with experience in a specific tool, describe a task and ask the contractor to describe how he or she would use the tool to accomplish it.
  • If you’re looking for a generalist, ask about a similar project the candidate has completed. Listen carefully for signs that the contractor was interested in helping the company succeed, not merely churning out the work.

Choose experienced contractors who will learn new tools quickly
Usually, contractors are both highly skilled and jacks-of-all-trades. Contractors who’ve been working in your field for a while are likely to have a lot of experience solving problems and performing tasks similar to what you need, but they may not be an expert with the exact tool used at your company. Unless you’re using highly specialized tools, don’t worry so much about whether the contractor has experience with the exact tool—just make sure he or she has experience on similar projects.

Contractors do a lot of self-teaching and are usually quick about learning new software and other skills. Sometimes, software programs from different companies are quite similar in how they’re used, so ask contractors what tools they do know and how quickly they’ve learned new tools in the past. If a contractor knows one or two similar tools and possesses the general skills for which the tool is used, it’s likely that he or she can successfully perform with a new tool.

Meredith Little wears many hats as a self-employed technical and travel writer, documentation consultant, trainer, business analyst, and photographer.

What’s the best way to find good contractors? Does your firm work with a pass-through agency or hire individual contractors? Post a comment below or send us a note.

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