Leading Freelancers Effectively: A Guide for Small Business Owners
As a proud member of Amanda Hughes’ inspiring community of small business owners, I’ve been fortunate to witness, up close, the heart, energy, and ambition that drive so many of us. Each person here is dreaming, building, stretching, and trying to make something meaningful. In that spirit, I wanted to give back in a way that feels authentic, useful, and connected to what so many of us experience behind the scenes.
So I contributed a guest blog to Amanda’s site: “Leading Well When You’re Working with Freelancers or Employees, Without Losing Yourself in the Process.” In it, I unpack some of the tensions and opportunities that emerge when you move from simply outsourcing tasks to stepping into a leadership role, especially in small, creative, growing businesses.
Below is a glimpse of what you’ll find in the blog:
Why leadership is a “pivot point”
When you first hire someone - whether a VA, freelance marketer, or contractor - you lean on their expertise, trusting them to do what you don’t have time or skills to do. But as your business grows, that role shifts: you gradually hold more of the vision, direction, and alignment. That shift doesn’t demand perfection, but it does ask for intention and clarity.
Leading with clarity (not chaos)
Working with freelancers is a dance. On one hand, they bring their own ideas, autonomy, and specialty. On the other, you need to frame vision, set expectations, and communicate priorities. In the blog, I share concrete suggestions, like how and when to check in, how to frame feedback, how to resist micromanaging while still providing guidance, and how to honour both their expertise and your goals.
Staying yourself (without burning out)
Leadership can feel heavy, especially when you're already carrying your own business, client work, and life responsibilities. So I also explore how to lead sustainably: how to set boundaries, protect your headspace, be honest with your freelancers about where you are, and acknowledge that imperfect leadership is still leadership. Your energy and wellbeing matter too.
Whether you’re just dipping your toes into hiring help or you’re navigating the growing pains of managing a small team, I hope this blog gives you insights, encouragement, and a few practical moves you can try right away.
If any part of it resonates - or raises more questions - please feel free to share your thoughts.
I’d love to keep the conversation going.
Click image to go straight to Amanda’s blog page.
