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Building a Team From a Freelance Business

Today, Ana Reisdorf, of Reisdorf Writing Services, and I are going to talk about something that many freelancers dream about, but can’t quite figure out how to achieve; expanding your business with a team. While we’ll be talking about it from a freelance writer’s perspective, I think anything we talk about here would apply to any freelancer who’s looking to scale their business by adding team members. 

At What Point Did You Decide to Hire Other Writers?

Ruthie: It does seem a bit like a “chicken before the egg” type of problem, because when do you know that you can add writers? Some people think they have to be overwhelmed, and that they don’t have enough work to hire more writers. Where were you at when you said to yourself, “You know what? I can add teammates.”

Ana: It was actually a personal thing. I had just had a baby, we were moving across the country. My business was just picking up. I was consistently making $4,000 – $7,000 a month.

I couldn’t be the mother of a newborn, a toddler, and a two-year-old, move across the country and do this business. My salary as a dietician was $5,000 a month, and now I was earning that much with writing. I couldn’t let that go. I worked so hard to get here.

building a team from a freelance business

One day, I got 3 – 4 requests from clients and I was like, “I need help.” So I went into my group and I said, “Who wants to help me?” Then, I think I got 35 requests. 

Finding the Right Writers

Ruthie: It was perfect because you had built this community full of people with similar qualifications and experience to your own, so you just had this pool ready to pick from. 

Ana: There they were. I ended up giving them all a paid trial article and having interviews. I interviewed around 20. After that, they carried the business for 3 months. 

Learn more about how to hire great freelancers here.

Ruthie: So how many people did you bring on your team at that time? 

Ana: I brought on 5 people.  They did everything. I legit moved across the country, took care of my baby, and just had to check in on emails and things like that. One day, I was at Legoland with my kids and there were just articles popping up in my inbox. 

Ruthie: The advantage you had was that you already had a network full of people who would be suitable to help you. For me as a content writer in the B2B business space, that can be harder because I don’t know too many writers who focus on my particular specialty. I know plenty of great writers, but not too many people who focus where I focus. 

What Were You Looking for in a Writer?

Ruthie: What were you looking for when you built your team? You managed to take 35 people who volunteered and narrow it down to 5. What attracted you to those 5?  

Ana: It was actually really easy. What attracted me was the quality of their writing. It was pretty easy to eliminate a lot of them. A lot of dieticians want to be writers because it seems cool and you don’t have to work in the hospital, but they’re not trained in writing. 

Writing Isn’t As Easy As Many Think

Ruthie: A lot of people think it’s easy. 

Ana: After that, I just gave them a phone call to see how we got along, and it’s been great. I have not had one problem with these people. 

Ruthie: That’s awesome. That’s great. I could see why you’d want them to be excellent writers. Again, we talked about how dieticians don’t want to hire somebody that they have to clean up after. 

That’s always what I’ve looked for when I’ve brought writers on too. I don’t mind some editing or tweaking. Since I’m more experienced, I can tell if they’re just stylistic tweaks, which I don’t get mad at. But to go back and try to clean up bad writing is just not worth it at all. You also get frustrated, whereas I’m not frustrated when I’m writing and creating.  

Ana: For the most part, they don’t need any huge edits. Every once in a while, one of them will be rushing something, but that’s just a human mistake. I’m sure that not every article that I’ve ever written has been the best thing I’ve written in my life. 

How Did You Establish the Workflow?

Ruthie: It comes and goes. So how did you establish your workflow? That means going from your clients’ requests down to your writers, and then from the writers’ article back to the client. What do those workflows look like? 

Project Management Tools

Ana: For a long time, we used Trello. 

Ruthie: Yes! Trello should pay me because you’re the second person who’s been on my podcast who’s mentioned Trello, and I’ve said, “Yay, Trello! I love Trello!”. I’m making sure I tag them when this episode goes live. I would die by Trello. 

Ana: It’s easy to use and it’s free. I would put in the title of the article, any details in the card, assign the writer, and we’d move it along in the process. I also created a form for our top clients and little nitpicky things that they like, like links, referencing, etc. And that was helpful for them.  

Ruthie: Like a kind of style guide or source of truth for your main clients. That’s a good idea. 

Ana: I wouldn’t do anything super extensive, because I personally hate those 40-page style guides. 

Ruthie: I’ve made a few and mine are usually 2-3 pages long with a lot of white space. 

Moving to Dubsado

Ana: It’s pretty straightforward stuff. My writers do all the 500-word articles because I just don’t want to do them anymore. In January we switched to Dubsado. 

Ruthie: You’re not the first person I’ve heard mentioning it. That’s the platform for creatives, right? 

Ana: Yes. It allows me to get a bigger picture of what everybody’s doing and what’s going on in the business. It also lets you send contracts, invoicing, and all of that stuff.

It’s been working ok, but I was thinking about going back to Trello. I’m paying for Dubsado, and it’d save me $25 if I didn’t use it. It seems more labor-intensive because I can’t copy things as easily, so I have to input each little thing. 

Ruthie: Well, that’s certainly feedback for Dubsado! You guys need to make it easier to duplicate content across cards/boards. That’s really important for me too, especially when you have repeated processes. 

I have a blog post checklist and a podcast editing checklist because there’s more than one person involved in that effort too. If I couldn’t copy those checklists between cards, I probably wouldn’t have them. I’d just say, “Look, y’all are just gonna have to know your parts. Just tag the next person in line in the comments. I’m not not doing this.” 

Ana: Yeah, it’s just a bit labor-intensive. 

How Did You Change Your Online Positioning After Hiring a Team?

Ruthie: So when you went for the team, how did you change your positioning online? That includes your marketing, website, social media, etc. If you change them extensively, how did you go about that? I think that’s another barrier for freelancers who may be excellent project managers and may want to build more of an agency model. How did you do that with your current assets? 

Ana: I was scared. I’ll be honest. I was really scared at the beginning to send my clients an email and say, “It’s not me anymore, it’s the team now.” And I thought they were all going to write back and be like, “We’re done.”

And that didn’t happen at alt. They were like, “Congratulations, your business is growing!” 

There’s been a handful of times that people have rejected me because I have a team, but that’s been maybe twice. The change has been gradual. I started by always mentioning the team in emails.

Right now, I’m going to call myself an agency more often on my website. I’ve been growing into this over the last 1 – 2 years. On Instagram, I promote the team and their individual skills more. 

Ruthie: Yeah, I’ve seen that. I like it.

Making Changes Over Time

Ana: It’s been evolving a little bit over time. I haven’t really had a specific method, but I do want to go more into really being an agency and not doing much of the writing myself. I just want to be the one who’s growing the business. 

Ruthie: That makes sense, especially with clients you’ve built a trusting relationship with. And anybody who dismisses it out of hand could already have what they think a team looks like in mind.

In many cases – especially people who have been burned in the past – will be thinking, “Oh, so here’s Anna in Tennessee, but her team is over in India. They may or may not be the best writers, and I’m not going to get great stuff.” 

[I was speaking to a general sentiment. I’ve worked with great professionals all over the world.]

I think that’s particularly important with writing. With some other types of creative work, like graphic design, it’s less of a barrier as long as ideas can be communicated effectively.

As long as everybody’s on the same page with whatever the intended design is, then they can get it done. But it’s much harder to do the sophisticated writing that your clients are expecting with somebody who’s a non-native speaker. 

Ana: Right. Like I said, there have been maybe 2 – 3 who didn’t like it and didn’t hire me. 

Ruthie: And you know what? It is what it is. You can’t please everyone. So thank you for sharing that. That’s really valuable information, and I know more than one person in both of our networks will be listening avidly when this episode goes live. 

building a team from a freelance business