What to Ask a Contractor BEFORE You Hire Them

This seems like a straightforward question, but it has a few layers to it.  Let’s take a look at each layer, one at a time.

Hiring someone, in any capacity, requires a plan.  A hiring plan must fit into your business strategy.  This doesn’t have to be a long, drawn-out process like those hefty business plans MBA students write.  But it does have to be specific to your business.  It can be answered with just a few key questions and simple guidelines.  And, fortunately, it can evolve with you as your business evolves.

The first layer is a question to ask yourself: Do I need to build, borrow, or buy?

This isn’t intended to make people akin to products sitting on a shelf.  Rather, it’s to help quantify a hiring need.  By quantifying a hiring need, we start to remove the debilitating emotions of fear and frustration that hamper our ability to make an informed decision.

When it comes to hiring, build indicates that you are going to train someone currently on your team.  The upside is that you already have confidence and trust in their capabilities, they just need to learn something new.  The downside is that it will take time for them to build their knowledge and develop a degree of expertise.

Buy indicates a decision to hire an employee.  The parameters can vary, it can be full or part time; temporary or regular (I don’t use the word permanent since most employment falls into the at-will category).  The upside is that you gain an immediate injection of their experience, skills, and abilities into your business and they quickly add value to your team.  The downside is that it can be difficult to find, assess and hire someone with all the skills and qualities we seek.  A “bad” hire is a costly mistake. Some studies put this cost at $15K per hire.

Borrow is when we temporarily engage a contractor to do work on our behalf.  The upside is that we can make a decision quickly and with little effort.  The downside is that we don’t always know what to ask in order to make an informed decision.

This leads us to the next layer of our hiring plan: understanding the nature of a contractual relationship.

Contractors are highly specialized experts in their field.  They are often hired for a specific outcome and yet, it can be difficult to assess the skills of one contractor to another.  In part, because they market their offerings in different ways.  And, in speaking with my clients, they sometimes hesitate because they don’t want to make a mistake.  This is where I remind them of the next reality of the nature of hiring a contractor…

The truest contractor relationships are transactional in nature.  We hire someone to create a website, for example.  They are a specialist who has the expertise and we only need them to do this one thing.  The specifics of the engagement can be determined through a discussion, but the end goal is clear, in this case, to create a website.   Consider another example.  If I saw my neighbor power wash her house using a high-powered washer, I may ask her to borrow it. I wouldn’t use it to wash my car or water my lawn, but I will use it for the specialized thing I need it to do, power wash my house.  This transaction exists regardless of my relationship with my neighbor.  She could say yes or no and they’d still be my lovely neighbor.  If they were kind enough to agree, I would use it carefully and provide the appropriate neighborly payment for their generosity.  The transaction would be defined during our discussion: when I wanted to use it, what type of soap to purchase, how long it might take, and other questions related to the transaction so I can get the result I want.

This leads us to the third layer and another question: What do I ask a contractor?

This is where the “rubber meets the road”.  If we’ve done our homework and considered the first two layers, they are most useful when we are face to face or Zoom (as the case may be) with someone we are considering hiring as a contractor.

Sticking with the website example, it’s plain to see that on any given platform, like Fiverr or Upwork, there are dozens of potential contractors and it would be easy to feel a little overwhelmed.  Contracting isn’t new and it’s only gaining popularity.  Sometimes, it seems like everyone is getting in on it as a “side-hustle” or full-time gig.  Or, if we just toss the proverbial, who do you know, question out to friends and family, there’s a good chance that someone knows someone who thinks they have the perfect person for the job.

The first key to having a productive conversation is to well, decide to have a conversation.  It’s not likely that making a decision based on their marketing or their references (as good as they may be) will provide us the most benefit without an interview.  An interview is a critical step in this process and should not be overlooked in the name of expediency.   Here’s a brief overview of a productive interview:

  1. Make them comfortable. Comfortable conversations are productive conversations. Steer clear of any personal questions, but you can ask other get-to-know-you questions such as how they got started or what they enjoy most about the work they do.
  1. Ask everyone the same outcomes-focused questions. Outside of my work as a recruiter for my entrepreneur clients, I’ve interviewed contractors for my business.  Recently, I was looking for a Facebook ads specialist.  Even with all the Facebook ads specialists out there, it was easy to zero in on a handful because I knew the outcome I was seeking.  I asked the same set of questions in all 5 interviews.  In the first 4 discussions, it was clear early in the conversation that they weren’t going to be a good match for me.  The 5th conversation was great in both skills and communication.  Hiring was a cinch at that point.

Outcomes-focused questions are different than task-focused questions.  I didn’t ask them to list for me the things they did (I’m not a Facebook ads specialist, I assume they know how to do their job), rather I asked about the types of outcomes they got for their clients.  We discussed project specifics, timeframe, industry, results, and communication preferences.  By asking simple, outcomes-focused questions, I was able to silence all the marketing speak and ask the questions I really wanted to be answered in order to gain the clarity I needed.

  1. Finally, don’t hesitate to ask questions that get down to the nitty-gritty. How many clients do they have?  What is their preferred method of communication?  How often do updates occur?  Is there an option to contact them after hours?  What type of guarantee do they offer?  What will they need from me in order to be successful? What additional costs may come up in the project? What steps can be taken if there’s a change in the project?

All of these questions help uncover potential issues before they become a problem.  Thus, increasing the confidence in a decision.