Teamwork makes the dream work

How to scale up with subcontractors without screwing up your business

Hire well. Have a system. Avoid the traps.

By Shea Lord |
February 25th, 2023
Teamwork makes the dream work

How to scale up with subcontractors without screwing up your business

Hire well. Have a system. Avoid the traps.

By Shea Lord |
February 25th, 2023

Read time: 4 minutes

Scale is the key to more profit and, if you do it right, more ease in your business.

But the first few times I tried to “scale up” and hire help from a subcontractor, it always went horribly wrong.

  • I ended up with more work and more stress.
  • I put my client relationships at risk.
  • I’ve been ghosted, lied to, and had people cancel last second
  • Sometimes I worked late nights correcting work.

Scaling up is easy to screw up. Especially if you don’t have systems in place to support the effort.

  • First note: “scaling” can refer to several areas of your business: people, hardware, locations, volume, funnel, marketing…

Here’s a quick guide (1,000 word limit!) on how to scale with subcontractors.

What is a subcontractor?

Subcontractors are other independent freelancers who you can team up with to get more/better work done. The client contracts you for a job. You contract someone else to help fulfill your contract.

  • They are not your employees on payroll.
  • From a US tax perspective, you need to collect their W-9.
  • Later you must issue them a 1099-NEC. It’s easy to do online.

“Does the client need to know I’m subcontracting someone?”
This really depends on your relationship with the client. Generally

  • Studios hire you for your portfolio. They will probably feel cheated if you hire someone else without informing them.
  • Direct clients don’t care who does the work or how. They may expect you to hire help.
  • Use your best judgment and protect your client relationship.

Hiring Well

Entire books and blogs are written on this topic. Here’s what I’ve learned.

  • Recommendations are the best. If someone you trust will vouch for their work, that person is less likely to leave you hanging.
  • Portfolios are often misleading— but you might not have time to dig in with a whole interview series. Look for testimonials and case studies.
  • Make room in the budget. If the payout wouldn’t get you excited, it won’t do it for them.
  • Only hire juniors for truly junior work. I don’t mind someone learning on-the-job, but they need to be experienced in learning on-the-job. If they’re stressed, you’ll be 10x as stressed.
  • Check their online attitude. We’ve all got critiques for the industry. That’s different from complaining and negativity. Look for people who actually enjoy the process.
  • Be VERY careful working with friends if you haven’t been on their team before.

Systems for scaling

Sometimes projects go haywire, but in a perfect world this is the system I aim for.

1. Smooth onboarding

  • The project scope and deliverables are clearly defined in writing
  • Payment terms are explicitly written
  • Any contracts or NDAs are signed
  • Assets are handed over
  • Get confirmation of understanding

Define the relationship and provide a big-picture view of how their role fits into the project. It helps to know how much responsibility they’re actually carrying.

  • Are you delegating a repetitive task to free up your time?
  • Is it a hand-off to a specialist for a specific part of the project?
  • Are you tag-teaming the work?
  • Are you building a team that needs to work together?

❗️1.2 Training (if applicable, part of onboarding)

When delegating a repetitive or simple task create a training video.
Case study: 
I do a lot of paid ads. At this point I’ve created specific presets and animated assets for some of my clients.

  • I can provide a .zip folder of these presets and assets along with a 15min demo video on how/when to use them for the specific client.
  • Now it’s nothing to hand off batches of ads to a junior looking for experience, cash, and feedback.

2. Clear timeline with deliverables

  • Break down the phases. Start with the deadline and reverse-engineer milestones on the calendar.
  • Cushion the milestones wherever possible. Aim for 1-2 days earlier than needed to allow time for course correction.
  • Track milestones somewhere: Notion, Asana, your Outlook calendar…whatever.

3. Kickoff

Hold a kickoff meeting the day the work is set to begin.

  • Ask them to glance over the assets before this meeting
  • Confirm that they have what they need.
  • Address questions that arise

4. Check-ins

If it’s your first time working with someone, and you want to make sure your project isn’t stuffed into an all-nighter before the deadline, have check-ins.

  • Define your method of communication. Email? Slack? Is the phone off-limits or expected?
  • Define how often you need updates, or how often your client will want them.

As a freelancer, I usually appreciate these. But it can cross over into hovering and micromanaging if you’re not careful.

  • New relationships have to build this trust. First-timers have more check-ins.
  • If you don’t trust your subcontractor to do the work, why keep hiring them?

5. Debriefing

I need to be better about debriefings. They’re very valuable when I do them.

  • It’s a chance to examine what worked and what didn’t in the project.
  • You can provide feedback to your contractors.
  • They can provide feedback to you. Win-win.

Freelancers (we) kinda suck sometimes

Ok. Sh*t happens. We all have horror stories.

(like the time my email server decided my own outbound emails were spam, but only the ones I sent to my client, so it blocked them without notice and the client didn’t get the deliverable…which I’m sure sounded like a lie to them.)

Sometimes subcontractors suck. And sometimes people have bad days.

If you’ve never dropped the ball, you haven’t been working long enough.

If you keep dropping the ball, you won’t be working long.