Help! I've Hired My First 5 Freelancers - How Do I Manage Them AND My Full Time Team

This week in the Human Cloud #42

Important Updates

  • Self employed people are four times wealthier than employees (holy 💩).

  • 30% of employees under 40 years old considered changing their occupation or field of work.

  • Squarespace see’s record results when their 100 person creative team was forced to be remote. According to Morning Brew, “Over the past year, the company’s in-house team produced some pretty elaborate campaigns, like these Renaissance-themed entrepreneur portraits commissioned from artist Ignasi Monreal, and ads that imagine characters such as Snow White starting their own Squarespace sites”.


Freelancer Highlight: Kemal Avdovic, Brand Design and Strategy

Profile photo of Kemal Avdovic
This past month we’ve seen Kemal kick total ass for a brand packaging project helping a US coffee brand build their next generation espresso product. According to their Head of Design, “We’ve had numerous referrals for New York designers, but nobody has grasped our brand like Kemal.”

Todays Topic: Taking the next step from hiring a freelancer to scaling through hiring freelancers.

TL;DR: Treat freelancers no different than employees. To help, follow these 4 steps.

  1. Ensure and maintain a clear company vision

  2. Measure through outcomes (output or KPI)

  3. Create a remote first environment

  4. Trust


In the end of the day, freelancers are no different than employees. Just really, really good employees. In fact so good that they can choose each client they work with instead of needing one employer.

But the working relationship is different. They don’t need to answer your emails. They don’t need your benefits or perks.

So let’s discuss 4 steps you can take today to start building a strong relationship.

Step 1: Establish and maintain a clear company vision

You own strategy. Freelancers own execution. And without an explicit vision you’ll execute efficiently in the wrong direction.

Why is this SO important? Because freelancers will think about you in their sleep. They’ll think of new ideas. Challenge old traditions. BUT if you give them the wrong vision those ideas will be in the wrong direction.

Step 2: Measure performance through outcomes

Freelance relationships are the ultimate win-win.

  • No interview warriors.

  • No org drifters.

  • Just performers.

When done right, freelancers start with a small project, show value, and if both sides see fit you keep working together.

To best shape your chances for success, align hiring and performance with outcomes.

There are two types of freelancer outcomes:

  • Output Outcome: What asset did you produce? Example: Success = Designing a deck.

  • KPI Outcome: What goal did you exceed? Example: Success = Designing a deck until $10m is raised.

Step 3: Create a remote first environment

Working in person with a freelancer is like following the speed limit in a Tesla. You can do it, but you’re capturing not even 10% of the potential value.

Instead, default to remote, with the goal of in-person interactions being relationship based, not performance based.

Example: Feedback

  • Instead of walking down the hall to voice your feedback, write down the collective feedback in a Google Doc, present the Google Doc before the meeting, then use the meeting to discuss the context behind feedback.

Step 4: Trust

Remember the strategy-execution relationship in step 1? Carry this over to everything from hiring to project planning to quality assurance.

Example: Hiring

  • Instead of spending 10 hrs writing a beautiful job description with 10+ requirements that you found from a comparable post online, write your objective, describe the problem, and trust the freelancer to teach you the price/timeline.


Want To Scale To More Than 15 Freelancers?

Chapters 8 and 9 of The Human Cloud teach you how leading enterprises create freelance programs.