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A Contractor Playbook For Companies That Are Small By Design

Now more than ever, the value your company creates is not dependent on your size, and the clutter of conventional growth often crowds out actual impact. In my experience, it’s far better to assemble only the truly essential resources and learn how to apply them well, all while staying deliberately, proudly small by design.

My agency has generated tens of millions of dollars in revenue growth for clients, transformed communities and helped address the largest public health crisis in a century. We did it all while staying intentionally small, and even choosing to get smaller. 

As you might expect, we do this in part through working with contractors, but we do so with care and a clear sense of purpose. We follow a playbook — which I’ve written about in more detail in my forthcoming book — that transforms contractors into high-performing members of my team.

Here’s how we do it.

1. Evaluate What Must Be Handled In-House

Not everything can be outsourced, or at least not everything should be. There’s you, of course, as the holder of the company vision. (Don’t outsource yourself.) Beyond that, conventional wisdom says to keep core competencies in-house, but I don’t think that’s always right.

My company has built a reputation as a creative agency with the technical chops to integrate complex systems into seamless digital experience platforms. My core team of employees and I do all the work of understanding our clients’ needs, articulating their goals and clarifying their visions. We see and suggest opportunities for integration, and then map out how they will function and interact. We determine how we’ll measure success with data.Why Jobs For The Future Is Leaning Into Outcomes

But as projects scale, we augment our team with high-performing contract developers to build what we’ve designed.

2. Choose Contractors Who Are Invested in Their Businesses

Contractors become contractors for many different reasons that may change over the course of their careers. For any contractor you consider, evaluate where they are in their business journey.

• Experience and exposure contractors are taking on contract work as a step along the way to something else.

• Fallback contractors are working as contractors because they lost or couldn’t find a job.

• Side hustle contractors have other jobs, so they may give most of their time and attention to something else.

• Career contractors choose the contractor lifestyle and invest in it as a business. 

I think career contractors are the only kind you should invest in. They typically want to grow and will put in the effort to grow with you as long as you make it worth their while.

3. Plug Them Into Your Systems (Never Plug Yourself Into Theirs)

Your company is the nexus where client goals and contractor value come together. You are the organizing principal — not anyone else.

Adapting your systems to the eccentricities of every contractor is wildly inefficient. Standardize your systems for working with contractors. Design them to be efficient and scalable. Where you can, build in a degree of flexibility. But then insist that all your contractors plug into your system. It’s usually more efficient for everyone, and, crucially, it’s more effective. You’ll deliver better value to your clients. That will likely lead to better opportunities for your contractors too.

4. Be Generous and Celebrate Their (Other) Successes

Transactional relationships are typically bad for business and worse for the soul. I think most people who choose to keep their business small understand this. We’re not doing this just for overflowing bank accounts. We want our work to be meaningful, and we want the same in our relationships.

So don’t treat your contractors like vending machines where you just put in your money and take out what you need. Build a real relationship, and give them more than just their fees. Support their growth with referrals, advice and glowing reviews. And celebrate their successes.

If they call you to share their excitement when they land a big new client, you’re doing something right. (If they hide it, it’s time for some self-reflection.)

5. Work With Them Exclusively

Once you find the right contractor for a particular capability, work with them exclusively. My contractors all know they have the right of first refusal on any job I have that matches their capabilities. (To this day, I haven’t had one turn any work away.)

Different capabilities may require different contractors, but wherever possible, seek to broaden their exclusive domain as you deepen the relationship. It’s more efficient for you and better supports your mutual success. So give them exclusivity for all that they can ably provide.

6. Be Transparent About Your Business (Within Reason)

Your business shouldn’t be a black box to your contractors. Within reason, let them see what’s going on inside. (If you don’t trust them enough to do this, you may need to reevaluate the contractors you’re choosing.) By showing them what’s behind the curtain at your company, you’ll also reinforce the norm that they can give you the same transparency into their business.

Contractors, if you choose the right ones, are business owners like you. You actually have a lot in common, and these conversations may be beneficial for you both.

7. Get Them Invested in Your Shared Success

Never ask a contractor to do free work that only benefits you. You can, however, ask them to invest in shared opportunities for success.

This must not be merely a semantic shift. Ensure that their investment has the real potential for a payoff that makes the invested time worth their while and make that payoff explicit along with any ask.

Pitching to a big potential client? Within a trusting relationship between you and your contractors, it’s reasonable to ask them whether they’re willing to contribute a little time and thinking to the proposal you’re writing. You may be surprised by how often some contractors don’t charge for that work.

If they know you’re invested in their success, they’ll also be invested in yours.

Contractors Can Make You Mighty

Integrate contractors thoughtfully into your high-performing teams. They can amplify your impact well beyond your company’s weight, while you adapt with the agility that comes from staying small by design.