How to be the Manager that Freelance TTRPG Writers Love Working With

There’s a lot of advice out there for how to be a ttrpg freelancer that companies love to work with. Hell, maybe I’ll write a post about that later. But there is less guidance for how to hold up the other end of that collaboration. As the industry grows, I’m seeing a lot of new companies of all different sizes enter the space, and expectations vary across each contract. In this blog post I provide some anecdotal experience that might help people in management positions understand what it’s like to be a career freelancer and how to best support freelancers to both facilitate that relationship and improve the product.

Why should you listen to me?

My name is Leon Barillaro. I’ve been freelancing in the ttrpg space for the last six years. For the last three years, freelance game design and writing has made up most of my income. I’ve worked with MCDM, Beedle & Grimm’s, Brotherwise Games, Kobold Press, Ghostfire Gaming, Renegade, and a bunch more.

I have managed several projects in this time as well. I managed and produced the solo game O Captain and its Crew Expansion, which had a team of amazing writers on it. I was also the managing editor of the first three issues of Unbound Magazine, an everything-but-5e zine from alumni of the Uncaged collection.

Disclaimers

First, this post is primarily about working with freelance ttrpg writers, because that’s where the bulk of my experience lies. Some of these pointers might be transferable to other areas—say, to hiring ttrpg artists, or to working with freelance video game writers—but I don’t make guarantees that they are universal.

Second, I will not be using specific examples of my time working with other companies in this post. This isn’t a post “about” a specific company or process. This is the culmination of me thinking out loud about how I like to manage and be managed.

Let’s get into it.

What it’s like to be a career freelancer

The first thing you can do is understand what it’s like to be on the other end. If you have never had a freelance contract, or you haven’t had one in a long time, the best thing you can do is go work on one (if your non-compete allows). But I know it’s not that easy, so here is the best explanation I can give of the challenges of being a full-time freelancer: I’m not working one job; I’m working 0-6 jobs at a time.

To make what I make now, which is enough to cover my expenses but little else, I have to write about 2700 words a week. 2700 words a week isn’t bad. It’s totally doable. But the problem is all that invisible work that comes with those words:

• Research and brainstorming
• Communicating to ensure both expectations and deadlines are both met
• An often-unpaid outline or pitching process
• An often-unpaid requirement to be active in the peer review and asynchronous collaboration process on a Discord server
• System, style, and IP mastery
• Administrative work, like searching for new jobs, managing and chasing down invoices, and accounting

…to name a few.

Information Flow

Answer is at the end of this blog post.¹ While you’re working it out, I think this is a great segue into the first topic:

Jokes aside, I think this question really illustrates how detail-oriented of a job TTRPG freelance writers and editors have. This is especially true when you work in a specific niche or genre, like D&D-inspired RPGs. There is so much to internalize, so much to remember, and most of it is so similar you might miss the differences if you’re not looking—or if you’re running up on deadline.

This is a reality of the trade. As a manager, you can’t download this knowledge into the brains of your freelancers, and it’s on us to remember it and use it effectively. But you can make this information as easy to find as possible.

There are three types of information that we need from you:

• Project and Workflow documentation — Timelines, Standards and Practices, Creative Briefs and Instruction
• System Information — Any information you can provide on how your game is designed, including but not limited to style guides and templates
• IP Information — What is canon to your setting, what toys are we allowed to play with, what do you know internally that the wikis do not?

Constructing documentation that allows us to access this information with as little friction as possible will make us able to perform our jobs easier and faster.

Building a Repository

I’m really passionate about information repositories and pipelines. I did a lot of designing and iterating on them while I was working at Future Proof. Sometimes, knowing where information can be found is way more important than knowing the information in the first place. Designing an information flow is so important because it empowers freelancers to find the things they need instead of constantly asking you for them. When you have people working across all time zones, including the ones that work while you sleep, this becomes especially important.

So, here are some tips for building documentation your freelancers will want to use:

Give Them a Starting Point

Give your freelancers a starting point, a place that they can come to when they need to find any piece of documentation. A Google Drive or Notion Page are good places to start. The idea is that if they start at this page, they should be able to access anything they need to complete the project.

You can give your freelancers all the information in an email, but watch out. If you see your project evolving over time, or styles changing, or the project scope expanding, then you need to add more documentation. Which means you need to send more emails. All of a sudden, there are so many emails. And every other client your freelancer is working for is also sending emails. Your client searches [PROJECT NAME] [CLIENT] and comes up with a swathe of emails. Which template did they want me to use again? Where is the original creative brief? It’s swimming around here somewhere. This is how headaches happen.

Shouldn’t The Freelancers Be More Organized? You might be reading all this and saying “maybe the freelancers should set up email filters.” And sure, maybe we should. I do. But this is also about removing the potential for error. Having all your information in one place where it can be updated easily is paramount for long-term complex projects. One time I was working out of an old template, because no one had bothered to email me the new one. A lot of wasted time and effort came out of that!

The Three Click Rule

Once you’ve set up your starting point, the next thing is to make it intuitive to search through. This can be subjective, but I think there’s one rule of thumb you can rely on:

In web design, there’s an idea that a visitor to your site should be able to find what they’re looking for within three clicks. They call it the Three-Click Rule. It’s helpful in information design, too.

How many clicks does it take to go from your onboarding document to the style guide? How many clicks does it take to go from your onboarding document to the creative brief? To the playtesting protocol? To the project timeline? For really obscure things (”In what year did John Smorgle take the Cursed Sword of Provinia”) you can ease up on the rule a little bit. It’s okay if people have to go digging for obscure lore or older concept documents.

BUT I find this to be a helpful rule of thumb for all the important pieces — keep them as close to the surface of your directory as you can.

Figure Out What’s Important

How do you know what’s important or not? One thing you can try is taking a stab at the assignment before giving it out to a freelancer. Open up a word document and start writing (or imagine that you are). What questions come to mind? What documents must you keep open while you write? Those are the important things. Usually for me it’s these three things:

• Template and Style Guide
• Assignment or Brief
• System Documentation (Like a core rule book)

Other things I find important:

• Tasks and Project Timelines
• Invoice Instructions
• Concept and vision documents

Please Don’t Talk Where You Document

Above all else, please make sure that your place of communication is separate from your documentation repository. If you post a document in a Discord channel where people are discussing the project, it will get lost. Even if you pin it, it can be hard to tell when there are new pins, and the notification that something even was pinned will get lost in the chatter!

Timelines

Life gets in the way of work all the time. This has always been true, but it’s especially true now. More often than not, something will go wrong: illness, death, or worst of all: scope creep.² You should always make sure you are building in some padding in your production timelines.

It’s also really important that whatever expectations you put on your team, you also adhere to. If you tell your team, “We really don’t have a lot of extra time, so meeting your deadlines is important,” then you gotta hold your end of the bargain, too. Make sure you’re strict about meeting your own deadlines—getting out briefs, returning draft feedback, etc.

If you have to change a deadline for any reason (your team couldn’t get feedback in time, or there was an issue with approving the brief for the next assignment), you have to allow the freelancer the option to negotiate the new deadline. After all, there’s a 99% chance that you are not their only client, and even a few days’ worth of timeline change can upset the balance they’ve worked out for themselves.

Holding yourself to the same standards as your freelancers shows them that you are valuing them and their time. It builds trust.

Clearly Define Project Stages

If you’re doing a project where you expect a lot of iteration to be happening, make sure it’s defined enough that the team actually has time to collect and draw conclusions on feedback before they start iterating again.

Don’t let people start writing before their outline or proposal has been approved. Don’t let people start iterating until they’ve received feedback. Don’t ask people to draw conclusions from playtesting feedback until the survey window has closed. Try not to put the cart before the horse!

RPG book making is fast-paced, and wrangling a large number of freelancers can be tough when you also have a million other things to worry about during production. We want people to get writing as soon as possible, because deadlines have been set and money isn’t finite. But as a manager, one of your responsibilities is to advocate for your freelancers, and make sure they have the resources they need. Time and Information are two of those resources. And with a little bit of the former, you can get the latter.

Growing the Relationship

Freelancers want to feel like they’re collaborators, not word machines. They want to feel like their creative input matters, and that the time they spent brainstorming these cool ideas for your project was not time wasted.

This can be difficult when you have very specific requirements for a project, or a really restrictive IP or brief. And some freelancers can be more skilled than others at fitting those requirements first try. But the more time you put in to growing your relationship with a freelancer, the more effective they’ll be in future projects. And the better it will be to work together.

Find Solutions Together

The best experiences I had on projects were ones where the lead developer wanted to know what my intent was for a certain moment or design, and we came up with solutions together that satisfied the requirements while honoring my intent. Most freelancers are happy to get on a call and hash things out or send a few discord messages back and forth.

Remember—you hired that freelancer for their unique perspective. This is doubly true if your freelancer has a marginalization and you’re asking them to write about that particular topic (e.g. a queer writer submitting a draft for a queer romance supplement). While freelance work obviously must fit the voice of the overall product, part of a director’s job is to respect their perspective and help them find a way to make it fit.

I know that it can be more cost-effective to quietly take our work and rewrite it for publication, but when you do this you rob us of a chance to grow—and yourself of a better freelancer on future projects.

Point Out Easy Things

If someone isn’t writing to word count, or using the style guide correctly, or missed an important part of the brief, TELL THEM. Tell them as early as you can manage it. Explain to us what we’re doing wrong, because it might be an easy fix!

There’s no standard expectations for freelancers, although I think there should be. Some companies are more lax about word count, where others are strict about meeting it. Sometimes a company can be both lax and strict, depending on the project. Word count is just one example, but there are others.

For my first few freelance gigs, I was working in google docs and using my own templates because the clients didn’t have them. The first time I had to use Microsoft Styles, I was in for a rude awakening. I wasn’t using them correctly, and my document was a mess, and my client gently explained to me what styles were and sent me a youtube video on how to use them. If they hadn’t done that, I might have continued to embarrass myself with more and more clients, and never been called back again.

Knowing how to use styles is absolutely something a freelance writer should know how to do! But you never know how much experience a freelancer has, so it’s always best to assume a lack of knowledge than carelessness or incompetence.

Positive Reinforcement

When you’re a freelancer, you live and die by the last job you did. When you do work for a company, you are creating a lasting impression on the people you work with. The work you do will define whether or not you get called back for another job, and whether or not your client will recommend you to other clients and help you expand your network.

TTRPG writing is very much a “what have you done for me lately” kind of gig.

Knowing this fact makes you wonder constantly: did they like my work? Did I do what they asked? Did I impress them? Enough to work with me again? There’s a really easy way to get us to stop wondering: tell us!

If you liked something about what we wrote, or were impressed with our ideas, our ability to stay on style guide, or thought we were communicative—TELL US. This will do a lot to put our mind at ease, especially during dry spells. It’s not just an ego thing (although for me it absolutely is); it’s also for our peace of mind!

Positive reinforcement can also be acknowledging your freelancers publicly. When you talk about a product, shout out the people who worked on it! This is also really good for marketing, because we love reposting stuff with our names in it.

Compensation

I’m saving the most important for last: if you want your freelancers to feel valued, you need to pay them what they’re worth. We’ve done this topic to death, but my personal rates at the time of writing (December 2025) are this:

Floor: 0.16/w

”Competitive” rate: 0.25/w

Maximum I’ve been paid: 0.35/w + $50/hr for meetings

When I say Competitive, I mean a rate that will make a freelancer choose your project over another one they might be considering. A rate that will make them clear their schedule to work on this thing. If you want to attract the best talent to your team, that’s the rate you should be looking at.

There are lots of places online where they’re talking about pay. I made a thread earlier this year. You can also read the EN World survey from a few years ago. There are a few more floating out there. Personally, I don’t think any company should be offering less than 0.10/w, and most should be paying way more.

You should also provide a contributor copy for your writers, and for the love of God please make sure your contributors’ names are spelled correctly before you go to print.

Conclusion

I have had some really, really good experiences freelancing. I have also had some painful experiences freelancing. I would say the best experiences are the ones where I felt like I grew as a designer and my voice mattered. The worst ones were the ones where I spent 20 minutes each day trying to find an answer to one question before I could start writing, or I felt like I was just padding out a word count or filling a quota.

It can be very difficult to write a post like this without sounding like a vent. I hope I straddled the line well and this was helpful for anyone looking to hire freelancers, or even just think about what they could do better as a manager of freelancers. Truly, the big secret is putting yourself in our shoes and trying to reduce the friction as much as possible.

I have loved freelancing in the TTRPG industry. Books would not get made without freelancers!

1. ANSWER: These are all terms for a game’s core dice-rolling mechanic for resolving an action your character wants to accomplish take. Typically called for by the facilitator. The player rolls 1+ dice and adds any applicable modifiers, and then the facilitator compares that to a number you’re trying to roll above to succeed, and uses that number to interpret the result. D&D 5e uses Ability Check, The Cosmere RPG uses Skill Test. Draw Steel! uses Test. The AGE system uses Ability Test. ↩︎
2. All three happened to me while working on the same project so I’m allowed to make this joke ↩︎