How to Make the Most of a Contractor Engagement

If you’re an entrepreneur who seeks to be a CEO of their business and not simply trade one full time job for a slew of part time jobs, hiring contractors is a relatively easy way to get help as you grow your business.

With one large looming caveat: how do we make the most of a contractor engagement?

When time is precious (as it always is) and we decide to hire a qualified contractor, we quickly feel a sense of relief because someone will be doing the things that we didn’t make a priority or didn’t know how to do. However, we are faced with the dilemma of making the most of this new relationship that while being transactional in nature, as we talked about here, it’s still a relationship.

And, relationships can easily go awry.

Fortunately, there’s a recipe that will help make sure that your business doesn’t become one of the statistics in the growing number of entrepreneurs facing hiring regret.

The formula is: Ready, Set, Go.

Getting ready to onboard a contractor is the equivalent of getting ready to plan a trip. You have a destination (the agreed upon outcome) and you’ll need to decide what roads are you going to take, what clothes you’ll need and what stops you may make along the way. The plan to get there (the goals and milestones during the engagement) will make or break the relationship.

Those lovers-of-lists who plan a trip may enjoy this part of the recipe. The I-still-need-to-do-laundry and when-are-we-leaving-again travelers may not find as much joy in this part.

The first step of the formula is GO. This is a thorough discovery of what you’ll need for the journey, if you will.

Here’s a list of questions to get your ideas flowing: How much access they will need to you/time during the project will you need to carve out to ensure a successful completion? What systems access will they need? (this can be very time consuming). What passwords or other sensitive information will they need to access? Will they need images from your marketing arsenal? Will they need your brand style guide? And, since there’s an end to the engagement, you may want to limit the level of access they have to your systems and be aware of the sensitive information that they may put on systems that you don’t manage.

The contractor will likely be able to give you an idea of what they’ll need, but it’s useful to do this assessment ahead of time so you aren’t spending valuable contractor time trying to figure out how to get them access to your information/accounts/platforms/programs.

The second step is SET.

Set is the check-in. This may occur right on the heels of ready. But, if you run into a snafu or if there’s a delay before they start working, you want to have a check-in to ensure that nothing has changed and that you’re still on track for the project completion. A lot can happen in just a week for either party. You can avoid any early misses in communication by confirming that everything is set to go.

If the project is relatively simple, this can be brief. If it’s more complex or a long-term engagement, this is where you can confirm your priorities, milestones and end goals. One of the possible struggles with a contractor is that they take on more and more clients and you don’t get the time and attention you thought you would receive.

And, the final step is GO.

Go is when you shift into the most critical aspect of any relationship, communication. This is where you find out if all the questions you asked during the interview gave you the answers you were seeking. This is where you find out if the contractor follows up and follows through on their commitments. And, it goes both ways. I’ll admit, I’ve been the roadblock to getting something done with a contractor. They needed me to make a decision and I was still working through the answer. I didn’t ignore them or assume they’d figure it out, I shared the reason for the delay and we adjusted. Crisis avoided.

I recommend a face-to-face meeting weekly or biweekly as part of the “GO” step. These regularly scheduled meetings prompt a great conversation and help answer lingering questions or brainstorm new ideas. If the contractor finds reasons not to attend these meetings or seems unprepared, you’ll be able to see this red flag and address it quickly.

The beauty of business is that it connects someone who needs something with someone who can help. Hopefully, using this simple formula with a contractor will help you and your business experience the beauty of this exchange.