Leading Well When You’re Working with Freelancers or Employees, Without Losing Yourself in the Process

Written my Sharon Smith a leadership coach and founder of Own Your Leadership and awesome member of our mentor group Get Seen Get Sales! Leading Well When You’re Working with Freelancers or Employees, Without Losing Yourself in the Process 

Running your own business can be a whirlwind – exciting and challenging in equal measure. When you bring someone on board, whether it's a VA, a freelance marketer, or an accountant, it’s a huge relief. You can finally offload some of the workload – yay! You’re desperate to seek their advice, trust their expertise, and appreciate their help. 

But then something shifts. 

You stop just listening to them and start realising that you need to give direction.

You’re not just the one asking for help anymore.  

You’re leading.  

Whether it’s with an employee or a freelancer, that change can feel daunting at first. 

So, how do you lead well without losing balance in the process? How do you stay true to yourself while stepping up to lead? 

The Moment When You Have to Step Up 

At the beginning, it’s all about asking for help. You rely on their knowledge and skills to guide you. But soon, you realise you’re the one holding the reins. You're the one setting the vision, and that's when the leadership shift starts. 

This doesn’t mean you need to have everything figured out or start micromanaging. It just means getting clear about what you want and communicating that effectively. Being a leader doesn’t require you to be perfect, but it does need intention. 

So, how do you make that transition? How do you lead in a way that feels natural and true to you?

Just Like Your Content Needs a Strategy, So Does Your Leadership 

If you’ve read Amanda’s post on Instagram strategy vs random posting, you’ll know that winging it doesn’t lead to sustainable growth.

The same applies when you’re working with freelancers or employees. 

You can't just throw tasks at them without a clear plan. At some point, you need to set goals, share your vision, hopes and aspirations, and be clear about what you want to achieve. The more intentional and strategic you are about your leadership, the better results you’ll get from your team or freelancers. 

Strategy is key – and it’s not just for marketing. It’s for leading too!

Working with Freelancers: Lead with Clarity, Not Chaos

When you're working with freelancers, the beauty is that they bring their own expertise. They know what they’re doing, and they’ll often give you great advice. But just because they’re the experts in their field doesn’t mean you should take a backseat.

You are the one who understands the bigger picture of your business. You are the one who needs to communicate your goals and expectations.

Here’s how to lead well when working with freelancers: 

• Share your vision and priorities upfront – don’t just send tasks 

• Be clear about timelines, updates, and expectations 

• Provide feedback early and often, but always with kindness – and celebrate their successes and the impact their offering will bring to your business! 

• Respect their expertise, but make sure your voice is heard too 

• Know when to let them lead, but also when to step in with direction. 

  
  

When you lead with clarity, you give your freelancers the space they need to excel while staying aligned with your goals. Ultimately, they too will want to do a great job for you, as you are their client. To ensure that happens, you should check in regularly and help shape the mutual project so both parties feel successful, and your working relationship grows.  

Leadership Doesn’t Have to Be Complicated 

Leadership often feels intimidating, especially if you’ve never held that role before. Many women in business shy away from taking charge because they don’t want to come across as bossy. But leadership isn’t about being in charge, it’s about setting direction and creating an environment where everyone can thrive, including yourself. 

Here are a few thoughts to help you step into leadership with confidence: 

• Know what you want and communicate it clearly 

• Don’t wait until you feel “ready” – just start leading 

• Trust your instincts – your leadership style is unique to you 

• Lead with both compassion and authority – if you’re bossy, unkind and authoritarian, you’ll soon learn freelancers won’t work for you.

  
  

Leadership isn’t a one-size-fits-all approach. You get to decide how it looks for you, as long as you’re stepping into that role with intention and self-trust. 

Leading with Balance – You Matter Too 

We all know how easy it is to get caught up in the busyness of running a business. You’re juggling client work, managing your team (or freelancers), and handling everything else. But the truth is, your business can only thrive if you’re thriving, too. 

So, how do you lead without burning out? 

• Set boundaries and stick to them 

• Make time for yourself – for thinking, for reflecting, for recovery 

• Be honest with your team or freelancers about what’s going on in your business 

• Focus on your leadership skills – not just your tasks 

• Acknowledge your growth as a leader, even if it doesn’t feel perfect yet 

  
  

Taking care of yourself means you’ll show up as a stronger, more focused leader – and your business will feel the benefits, too.

Want to Get Clear on Your Leadership?  

If any of this resonates with you, then the Your Own Leadership Audit could be exactly what you need. It’s a free, quick self-assessment designed to help you reflect on where you’re at with your leadership, identify areas where you might need support, and take actionable steps to grow in a way that works for you. Whether you’re working with your first freelancer or leading a small team, this audit will help you gain clarity, stop second-guessing yourself, and feel confident in your role. 

👉 Your Own Leadership Audit 

About the Author 

Sharon Smith is a leadership coach and founder of Own Your Leadership. She supports business owners and leaders at all stages – whether you're hiring your first freelancer or leading a growing team – to build clarity, confidence, and leadership skills that feel authentic and sustainable. With a background in people management and coaching, Sharon blends practical tools with emotional intelligence to help you lead in a way that works for you. 

👉 Find out more at Own Your Leadership.