What Hiring A Writer Taught Me About Being An Effective Boss

Tammy Danan
December 7, 2022

If you’re a full-time freelance writer, there are two things you’ll most likely do next:

  • hire a VA to help with the admin tasks of your growing business
  • or hire another writer a.k.a. another you.

It’s been a long time coming and I decided to hire another me.

Or so I thought..

I knew it wasn’t going to be easy, sifting through application after application. Reading one sample after another. I did prepare myself for that, but I was barely scratching the surface. There are so many things that go into hiring a writer that I did not realize. More importantly, so many lessons learned that I will forever carry.

You’ll have to invest time training this person

For some reason, part of me was thinking there’d be no training involved. Or at least, only little training. I don’t even know where I got this idea but I thought I just have to show this new writer the ropes, so to speak, give them a solid content brief, and it’s all good.

It’s not.

Perhaps this depends on the type of writer you hire, and how long they’ve been in the business, but to me, there will always be a bit of training involved. Especially if this person is going to be writing for you regularly. In my case, I have my own standards and the training part mainly focuses on making sure my new writer will reach those standards and maintain a certain level of quality work. That said, investing time to train this person is something I wish I’d known beforehand. Because that is time I have to take away from my usual business tasks like admin work, writing, and editing. It may or may not be worth it, depending on the capacity of the new writer, but knowing it beforehand could’ve helped me make a better decision.

Being a freelancer and being a boss are two totally different things

This is a big one. Doing things solo for a very long time, I became accustomed to my system. I operate on my own time and my own schedule and I never had to think about anyone else. When I hired someone, I learned to wear another hat—the boss hat. Sure, I keep things casual and light with my writer, but it’s important to set some ground rules and maintain a level of professionalism between us two.

Simply put, this business shift taught me to be a boss. And that setting rules doesn’t mean you’re bossy—I’ve always had that impression on myself whenever I set rules for others. I had to teach myself that in order to be an effective boss, I needed to see myself as a boss, and act like it. I’m not just a freelancer anymore; there’s another role I’m playing and I need to take it seriously. After all, we’re running a business here. We’re not playing around. 

This new writer is a different person and a different creative. Not another you.

I wish someone had told me that hiring a writer means working with another person. For some reason, I didn’t clearly understand this until I was already working with my writer. You may have standards and expectations but if you’re a freelancer going this same route, it’s important to remember that you’re not hiring another you. So don’t expect this other person to be just as good as you or just as dedicated as you or worse, be the exact kind of writer that you are.

Sticking to these expectations will only hurt you, your business, and most definitely, your writer. This is another person, let them be the type of writer they want to be. Just as how your previous editors and clients allowed you to figure out and pursue the kind of writer that you wanted to be. Whether that’s a writer or a VA you’re hiring, when you make the shift from solo freelance to bringing in help, keep in mind that they’re not you. Allow them to be their own person.

Patience and creative boundaries are important

Hiring and working with someone is a test of patience. There will be some adjustments and I was never good with adjustments so this was tough on me. Thankfully, my writer was patient—I learned from her a lot. Patience and creative boundaries are important points to maintain when you hire someone. I had to keep reminding myself that my new writer will easily understand some things and will take time to learn the others. I have my own process of doing things but meeting her halfway and being open to her process isn’t such a bad idea. To me, that’s what a creative boundary looks like—to set rules so standards would be met but at the same time, to give my writer the space to explore her own creativity.

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As a freelancer, you'll get to a point where you have so much going on you can’t do it alone.

Had I not hired someone, I’d be stuck where I was and my business won’t grow. Bringing in a new person, outsourcing some work, having someone to help you out means adjusting and learning and growing. Be open to the lessons this experience will teach you.

It wasn’t a very smooth process for me, hiring a writer, but it’s a business move worth making.

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