A Solopreneur’s Guide to Delegating Freelancers

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🖊 This article was last updated on June 12, 2019

If you’re just about to hire your first freelancer you may be a little worried about delegating tasks. Or, perhaps you already work with freelancers but the process isn’t going as smoothly as you’d hoped. Either way, delegating is a valuable skill to have if you want to grow your business.

Many solopreneurs struggle to delegate for various reasons. Some don’t wish to appear ‘bossy’, or they don’t really know how to ask for what they want, others find it hard to hand over responsibility of their ‘baby’ to another person they have never met. The trick to delegating successfully is to have a system and structure in place.

Here are the 9 steps you can follow to ensure a happy delegation process!

1. Hire the Right Freelancer

Even though this takes place before you can actually delegate anything, it really is the first step in getting delegating right! If you don’t have the right person for the job, then nothing else will matter.

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One important thing to keep in mind when hiring freelancers… If you need help for multiple tasks, you may be tempted to hire just one freelancer to cover all areas— I see so many job ads looking for ‘all-rounders’. While this can work, it can also backfire.

Throwing the net too wide in terms of skills and expertise, you may end up with someone who knows how to do all of these things on a basic level, but may not be an expert in any of them. It makes more sense and will be much more effective and productive to split your tasks and hire an expert in that area. Finding the right freelancer with the right skills will make delegating those tasks a better experience for everyone involved!

2. Treat Freelancers Like a Business

Freelancers are basically a fellow solopreneur and they are their own businesses. Instead of viewing them as your ‘employee’, start seeing them as a business/partner you are collaborating with. This instantly changes the dynamics. You wouldn’t tell a partner how, when, and where to do their work. Freelancers have their own systems and ways of doing things, and you should respect that.

3. Build a Relationship First

Of course, it is tough to trust someone you’ve never met. That’s why building a relationship with a freelancer is important from the very first contact. Get on FaceTime, do a Skype chat, Google Hangouts, whatever works.

Make use of video as well, as seeing someone while you talk to them helps establish a connection and you get a better ‘feel’ for that person. It also helps them get a sense of you and your project.

4. Communicate Schedules and Expectations

Communication is key! Especially when it comes to schedules, deadlines and setting expectations. It’s not just about YOUR expectations. Ask your freelancer what they expect and need from you to complete the tasks.

Freelancers usually work with multiple clients, and the more information they have from you, the better they can manage their time and your project.

5. Got Priority Tasks? Communicate them!

Connected to the above tip but I’m always surprised how often this step is forgotten. Your freelancers can seem superhuman sometimes but they aren’t mind-readers!

If you have time sensitive tasks but don’t communicate that, then you can’t get your knickers in a twist when your freelancer doesn’t deliver them to you first. Delegating isn’t just about maximising your own time and productivity, it’s also about enabling your freelancer to do the same.

6. Be Available

A common frustration for freelancers is that they can sometimes feel abandoned with a task. If they have a question, they can’t just knock on your door and ask. Let your freelancer know that you are available to answer any questions they may have, especially in the beginning when everything is new.

You can set up a response policy that works both ways. For example, with the freelancers I work with, we have a 1-day response window. When they email me, I try to respond within 1 day and vice versa. This way, no one is waiting around for answers, which can help keep your projects on track.

7. Use Collaboration Tools

Email is a great but there are other options out there to keep the lines of communication open. Collaboration tools and online shared work spaces can be a really effective way to share documents, thoughts, ideas and quick questions.

Popular tools include:

  • Google Drive: a cloud-based platform great for sharing and editing documents
  • Asana: A project management tool great for tracking progress, deadlines and deliverables
  • Trello: Another project management tool for tracking project progress
  • Google Hangouts/Skype: A video conferencing app for one-on-one calls or group meetings
  • Slack: Communication tool, great for remote teams


Ask the freelancer which platforms they use/prefer. Chances are, they already have other clients on that same platform and they can work more effectively if their attention isn’t being ‘pinged’ in multiple directions by constant notifications.

You may also wish to add this to your response policy. Dedicate a time of the day where you check in, send or deal with notifications.

If you work with multiple freelancers across different projects, only add the freelancer to the appropriate project boards. I think we can all agree that there is nothing more annoying (and counter-productive) than having to scroll through hundreds of messages just to see if there is anything relevant or actionable.

8. Don’t Micromanage

Speaking to the perfectionists and control freaks in the room! We can all experience a little anxiety when giving a stranger responsibility for any part of the business we have strived long and hard to build. But, the fact that you are now in the position to do so, is in itself a success!

Learning to let go is essential to successful delegation. You can’t hold on to the reigns and ask someone else to ride the horse! Micromanaging is never productive. You hired a freelancer for a reason, so let them do what you hired them to do!

By following the steps above, especially building a relationship, communication and setting expectations, you will get to know your freelancer better, feel more comfortable, and trust will come.

9. Have Guidelines for Specific Tasks

If you like things done a particular way… Communicate them! Expect to spend some time in the beginning training your new freelancer, especially if you have certain tasks that require specific knowledge. It’s a good idea to have guidelines for such tasks that your freelancer can read before they begin or refer back to as and when they need.


Delegating isn’t a natural process for everyone but it is something you can get better at. By learning to delegate effectively, you free up your time which makes you more productive as well as the freelancers you rely on. Handing over responsibility can be tough but it’ll be worth it!

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