5 Questions to Ask When Hiring A Contractor

When I propose to people and business owners as a Marketing Advisor for RT Consulting, I ask a lot of questions. I have hired a handful of contractors to help me with client projects. Hiring a contractor can be beneficial to both parties to reach the goal in mind. Success does not happen overnight, but asking the right questions can get an idea if this partnership can get you there.


1. How can you help me?

Ask open-ended questions so the contractor can talk about what he or she has observed during the meeting. If the two of you just met, be weary of the answer to this question. If he or she has done research on you beforehand, listen carefully; otherwise let them ask you questions to help them accurately answer you.

2. What experience do you have working in [fill in the blank] industry?

In a perfect world, everything would be simple. In a perfect world, every industry would be marketed and advertised flawlessly. The reality is not every industry is the same. Each industry may have similarities but it stops there. Advertising for a personal trainer is far different from advertising for a finance advisor.

A contractor with direct experience in your specific field is beneficial. If you (the prospective client) are willing to spend time and coach the in’s and out’s of your industry it will cost you at your own expense.

3. How are your communication skills? Give me an example of how we would communicate before, during, and follow-up for meetings?

A contractor is excellent at telling you about his or her communication skills, but the proof is in the pudding. If he or she says they are available anytime and doesn’t pick up the phone at 10am, 4pm, or 7pm, then something isn’t right.

4. How many other projects do you have going on now?

A contractor should never reveal how much “work” he or she is doing at the same time. Your project and business is important. Make sure you receive the answer you want to hear. If you are looking for work to be completed per week or bi-monthly communicate it.

5. What is your biggest success? Biggest failure?

Contractors can talk about their successes all day long. The experience doesn’t come without failures along the way. If the contractor can show you his or her failures, do you see his or her character? Did he or she take responsibility? How was the situation turned around?

There are plenty of question that can be asked when hiring a contractor. These are the top five I have found useful when considering to hire someone. What are some of the questions you asked when hiring a contactor?