THE HUMAN SIDE OF SUBCONTRACTING

For freelancers, hiring your first subcontractor is a business milestone. You've built enough momentum to need another set of hands, but the challenge is that those hands will be attached to another human being with their own habits, preferences, and needs. 

When you start working with subs, you're entering somewhat uncharted territory. There's a good chance it's been a while since you've worked closely with other people, and even if you have an agency background, relationship management was likely someone else's department. HR handled awkward conversations. Project managers chased deadlines. You just...did your work.

Folding other people into your business means planning for all the things that can happen when humans start human-ing. While you can’t always prevent life’s speed bumps, here’s our best roadmap for expecting the unexpected. 

1. Differing Communication Styles

Some people respond to email notifications as they come in. Others check theirs twice a day. Some people write novel-worthy project updates. Others send the thumbs up emoji. Neither approach is inherently wrong, but mismatched communication styles can create unnecessary stress if you don't talk about them upfront. 

Before you onboard a subcontractor, make time to speak face-to-face (or at least over Zoom). A low-pressure interview and a good conversation can help you see where you’re aligned and where you may need to manage expectations.

If the vibes are good, it’s always wise to put things in writing. A thorough subcontractor agreement should outline how and when you expect to touch base so no one is left hanging. 

2. Deadline Problems 

Life happens, and the more people you have involved in a project, the greater the likelihood that things will occasionally go wrong. Kids get sick, internet providers go AWOL, and sometimes subs just underestimate how long a job will take. 

None of those situations automatically mean you've hired the wrong person, but they do mean you need to build some breathing room into your schedule. One of the biggest mistakes freelancers make is giving their subcontractor the same deadline they've promised their client.

Create a buffer zone that allows for emergencies. The amount of wiggle room you need will depend on the size of the deliverable, but the goal is to give yourself a realistic amount of time to make revisions, find outside help, or take a project across the finish line yourself if need be. 

3. Feedback Anxiety

One of the trickiest parts of subcontracting is discovering that different people have different definitions of "finished." Especially when the relationship is new, your subcontractor may sincerely believe that they’ve delivered exactly what was in your scope, and you may still have some notes. 

Criticizing another person’s work can be awkward, but it’s important to find a kind way to help your subs deliver what your clients are looking for. The best way to do this is by keeping feedback focused on the work, not the person.

Simply saying, “This isn’t what I wanted,” will frustrate your sub without getting you any closer to quality work. Instead, be specific about the changes you’re hoping to see, and provide examples when possible. 

Don’t forget the power of positive feedback, as well. If your sub nailed the tone, solved a tricky problem, or made your life easier, say so. People tend to repeat the things they know you value.

4. Mismatched Work Rhythms

Procrastinators have been making "do it immediately" people nervous since the dawn of time.

Some subcontractors prefer to start knocking out projects the day they receive them, and others may wait until a few days before the deadline. Both can produce excellent work — the problems come when you have no visibility into what's happening.

If you don’t establish project checkpoints, you may start assuming the worst when you go a while without hearing from your sub. 

Without micromanaging, determine what you need to see to feel confident that a job is on track. Especially for larger projects, building small deadlines and status meetings into your scope will save you from worrying that your sub has forgotten about you anytime they get quiet. 

5. Changes in Capacity

Freelance businesses deal with a lot of ebb and flow. Subcontractors make it possible to take on more work when you have a surplus, but that is rarely guaranteed from one month to the next.

On top of it all, your sub’s bandwidth may not always be consistent. Subcontractor relationships require you to constantly check in with each other and reassess what you’re able to commit to, and that’s ok — as long as everyone shares that understanding. 

Be realistic about the fact that workloads fluctuate. Don't promise consistent hours if you can't guarantee them, and don't assume your subs will always be available when you need them.

Build your working relationship on honest conversations, and you’ll have a lot fewer awkward surprises.

6. Worst-Case Scenarios 

Sometimes, things just don’t work out. 

You don't need to spend a lot of time worrying about what will happen if your subcontractor disappears or your work styles are hopelessly misaligned, but you do need a plan. 

Use your network to build a shortlist of qualified people you could approach for last-minute assistance if you’re faced with having to tag in a new sub. Having a contingency plan may seem pessimistic, but it can actually save you from wasting mental energy on hypothetical disasters. 

Know your dealbreakers, decide who you will call if things go wrong, and move forward fully expecting good things. 

Working with subcontractors isn't about finding people who never miss deadlines, never misunderstand feedback, and never experience real life (largely because those people don’t exist). The goal is finding professionals who communicate honestly and solve problems with you. 

Subcontractor relationships are human relationships. When you make room for humans to be human with clear expectations, good communication, and a little grace, you can do so much more than you ever could alone.