Tell Me About a Job that Went Bad

“Tell me about a job that went bad.”

That’s one of the tips I got recently for how to screen independent contractors pre-hire.

I’ve been hiring independent contractors for over two decades in business. Sometimes it has been a good experience. Sometimes … well … let’s just say that I’ve learned from my mistakes.

So I decided to ask 8 small business CEOs and entrepreneurs for their single best tip in hiring independent contractors. I got 8 different viewpoints, including the above tip for what to ask prospective contractors which came from Jonathan Fields of Awake at the Wheel.

The rest of the advice was just as interesting. All of it was wise and spoken from the voice of experience. Many thanks also to Tim Berry, George Langan, Jonathan Fleming, Yvonne Divita, Barry Moltz, Ramon Ray and Robert Rutkowski for the tips!

The full post, including the tips from the experienced business people, is a guest post I wrote over at the Elance blog. Check out: Tips From The Trenches for Outsourcing to Independent Contractors.

Then share your best tip. What single piece of advice would you give for hiring great contractors to staff a project?


Anita Campbell Anita Campbell is the Founder, CEO and Publisher of Small Business Trends and has been following trends in small businesses since 2003. She is the owner of BizSugar, a social media site for small businesses.

10 Reactions
  1. Hi Beth,

    Good post. I would advise making sure that the contractors are dedicated to the project and not spread to thin with other work. If they are working full time on my project, then I should should be their only client at the time. Since I’ve learned to ask “how many other assignments do you have”, I’ve gotten much better service.


  2. Find the right fit between the contractor and the job. Ask “have you ever done this kind of project before”? Then ask for examples. You’d be surprised how many freelancers and contractors say they know how to do something but don’t have a clue! Your in for a miserable frustrating time if that happens!!!

  3. I’d include a question about their current workload as well. Many take on too much work and they then have trouble focusing on each individual project, then something slips through the cracks or possibly takes months to finish. And in some cases, “Are you insured?” doesn’t hurt either.

  4. I would have to ask them how much time can they devote to my project. A clear understanding about the hours that will be worked is needed.

  5. Very informative and useful. Thanks.

  6. Great additional questions! So, so far, we have reader comments suggesting:

    – how many other assignments do you have?
    – have you ever done this kind of project before?
    – are you insured?
    – how much time can you devote to my project?

    What other questions are there?


  7. Here’s a pretty funny one that I came across on the net for “on site” contractors – “Will I hear loud music, objectionable language or find cigarette butts laying around?”

  8. Here’s one –

    What do you hate about working with clients who hire you?

    The answer could be revealing in many ways. If the contractor starts going on and on with a laundry list of things he or she hates, it would be a red flag. Who needs a complainer.

  9. Martin Lindeskog

    One solution to get rid of lots of paper work is to “rent” your own employer. Have you heard about this in America? It has become pretty popular here in Sweden.

  10. I would have to say “do you have any other work obligations going on at the same time?” I’m with Chris, I think some people think of only the money only. Once they get the assignment, then they realize they don’t have enough time.