A Dungeon Master's Guide to Roleplays

This guide is for those who long to write collaborative stories that see completion. If you or a friend has a story idea but no idea where to start or how to lead a group of writers, this guide is to provide practical ways to create an enjoyable experience for you and the writers who join your journey, hopefully until the story's end.

Storybooks and roleplays do not exist without an initiator. Those stories do not see an end without strong leadership. Fortunately for you, leadership isn't merely an innate ability: it's a skill to grow in, and you're not figuring everything out alone! You will be recruiting a team of writers with their own strengths. You will learn to grow and lean on each other.

Let's define some terms real quick so that you know what I mean when I'm talking about the following.

Defining the Terms

- Roleplay: A collaborative story written with other writers, short or long form, with varied levels of story structure and depth.
- Storybook: A collaborative, structured long-form story written with other writers comparable to a novel in scope/length.

Obligatory Qualifier
My way is not the highway! I am just here to help. Some things I suggest may not work for you, your frame, your preferences, or your writing style. I am, however, trying to give generalized advice less about the subject matter of your stories and more about group management and leadership, which is a broader subject. This is how to develop those skills in this specific, niche context. IE: roleplaying.

My "Resume"
Everything I've learned has been through the fire tunnel of failure! I learned many things the hard way and took notes. Now, after many years, I have several completed storybooks under my belt (viewable under "Roleplays" in my bio) and plenty of roleplays that saw conclusions to their stories. I've also been a GM for several D&D campaigns!

THE HEARTBEAT OF ROLEPLAYING
Let's be real: storybooks are voluntary group projects. Because there is no academic evaluation or monetary compensation, you need to understand that those who are doing this are doing it for the love of the game. If they are not loving the game, they will be discouraged from continuing. At the end of the day, roleplays are meant to be fun!

WHY DO PEOPLE DISENGAGE?

Personal Reasons

- Life happens. Conditions for commitment change. Asking someone to sign up for a big story is a big ask. Be it life crises, unexpected opportunities, unexpected responsibilities, or new passions, sometimes it just gets busy, and people's capacities change.

Incompatibility

- Sometimes you can communicate everything clearly, and people will still misunderstand what they're signing up for. Sometimes they will think they know what they're signing up for until they experience it. Sometimes people realize it's just not working. They want something else out of the experience/story that they can't get from you. And that's life!

Weak Leadership

- Loss of vision. If you don't have clarity on what you want and where you're going, neither will the people you're inviting on the journey. That, or it's become a vacuum for everyone's ideas. If you can't commit and point them in a direction, everyone will flounder, and you won't go anywhere. Unless the journey is the goal, many people find floundering unfulfilling and tiresome. Most people want to read stories that have a purpose, which means you need purpose.
- Your writers feel unappreciated. Nothing kills camaraderie faster than when people feel overlooked, unheard, and unimportant. If there are no outlets for people to meaningfully contribute, people don't feel like they're needed, or their ideas are only ever shot down, it could be a sign that they're incompatible -- or that you're being too inflexible. Every situation is different, but groups fall apart when people don't feel wanted.
- You have overwhelmed your crew. Be it infodumping more than they can process, or delegating more than they can handle, if you've made it feel like you're unreachable and/or setting unreachable standards, no one's going to want to stick around for all of that labor if you're not helping carry the weight.

There's nothing you can do about the first two categories except recieve and release those writers with grace. The latter category is what we're here to address, as that's something you can actively reflect on for growth!

So, how can you foster a positive, engaging, and welcoming environment? How can you prepare a story everyone is excited to commit to? How can you find people who are compatible with you?

WHAT HELPS PEOPLE ENGAGE?

Clear Expectations

- The pantsers and the wing-it folks are going to hate me for this, but clear expectations set the stage for success. Why? Because people will know what they're saying yes to. Clarity builds confidence. Think of it this way: you are inviting people into your home for the evening, and creating clear expectations is turning the lights on. If you invite them into a dark house, they're unlikely to feel welcome. It will be more confusing than anything.
- What do I need to set expectations for? Here are some things you may want to think about:

- Yourself: What are your expectations for yourself as a leader and what do you intend to uphold regarding your own behavior?
- Communication: Where/how you will communicate (platforms), frequency, availability, respecting one another's time and commitments as well as individual lives, etc.
- Standards: Behavior, conflict resolution, reading/writing level, the culture/tone you want to set
- Preferences: Story length, post length, formatting, POV, writing style, boundaries for subject matter, etc.
- Time Commitment: How long do you expect the story to take (if estimatable)? Do you want to see it through to the end?
- Collaboration: What will it look like on the scale from independent to dependent?
- The above list is not exhaustive, but there are many things to take into consideration. The tone you set sets the tone for all of your future interactions with the writers who sign up, or the writers you recruit.

Vision

- Have a clear vision for the story you want to tell. What are you inviting them into?
- What kind of story do you want to tell? What are the boundaries and limitations? What are you comfortable or not comfortable writing? What is the end goal of the story and its arc? What themes are you wanting to explore?
- How much do you need/want help fleshing out the story re: worldbuilding, plot, and characters/character roles? Is the world already built? How much say will your collaborators have in the world, the plot, etc?

Treating People Like People

- The rules bend when people need them to soften. Rules are not there to never be broken. They are there to give stability and consistency. They are the solid ground to land on. The goal is stability with kindness, with the latter being the most important. The writers you're working with are not a means to an end. They are people, and hopefully ones you will grow in friendship with as you work on this project together.
- Be humble. You may be the leader, but leaders are not there to boss people around: ultimately, they are there to serve the needs of others. So if you're signing up to lead, you're signing up to serve.
- Be human. Yes, treat yourself like a person, too. Ask for help when you need it. Don't feel like you have to do everything yourself, and welcome ideas and strengths that others have to offer.

THE PRACTICALS

PLANNING
I know. I know. Unfortunately, even though things never go exactly according to plan, things will always happen more smoothly with a plan. Planning does not guarantee what will happen, but it creates the foundation for success. As the leader you will be the primary coordinator unless you choose to delegate that task to someone else, but I recommend being the one to initiate.

When You Write

You will need to pull out a calendar. Find out when everyone is free. Work with different timezones. Schedule differences. Find something consistent: weekly, biweekly, monthly, that you all can commit to.

Where You Write

You will need to meet together somewhere you can all talk, brainstorm, and write at the same time. On YWS, the best resource is our writerfeedpad. Outside of YWS, there are several live pads that are free to use that don't require an account, like pad.riseup.net.

What about the story? That's right, you'll also need to plan for the story! Sure, you have a premise, you have a world (maybe), and you have a stacked deck of writers and character ideas. What now? What's the story?

Plan the Plot

Make an outline. Treat it like a real story, because it is one! You're basically writing a novel together! It will save you so much pain further down the line if you have a clear beginning, middle, and end. You can flesh out the details as you go, but if you all commit to the big story beats beforehand, then everyone knows what to anticipate, what to be excited for, and what to mentally prepare for. It makes everything so much easier emotionally and far less stressful, because then you're not having to figure out how things end in the last chapter, and you're not getting lost along the way!

HOW TO SHOW UP AS A DM
While there are many leadership styles, there are some unifying qualities. Part of being a good leader is understanding people and what they need, even in something for fun, like a roleplay. So here's some guiding tenets.

Be Consistent

Show up even when others don't. Be welcoming and kind even when you don't feel like it. Follow through on what you say you'll do. If you are committed to the project, it inspires others to be the same.

Support Your Writers

- Be willing to hold people's hands, especially at the start. Be prepared to answer questions, to seek understanding, to provide understanding, and to be patient until it is found. Make sure writers have everything they need to succeed: be that information, context, or someone to bounce ideas off of.
- Give feedback. Encourage people in the areas they can grow. If someone's struggling, be attentive, available, and work through the story/writing/character kink with them as much as you can.
- Encourage! Notice what people are good at and point it out. Pay attention to where people shine and encourage them in those areas.
- Celebrate together. Celebrate successes together, geek over the story together. One person’s win — for the story or in life — is everyone’s win!
- In the same way, one person’s struggle is everyone’s struggle. If someone in the crew is having a hard time, encourage everyone to build them up and be there to lean on.
- Ask people if they need help! And be specific! If you notice someone struggling, it never hurts to ask.

Build Confidence

- Value your writers. Treat each one as necessary. They are all important and bring something invaluable and unique to the project.
- Encourage! Yes, x2! Tell writers when they do a good job. If they write something you adore, tell them, and tell them why. Foster an environment where you do this for each other.
- Ownership. Encourage your writers to own the story by creating opportunities for them to speak into the world, the plot, the characters. Let them be truly involved. Hear their ideas and incorporate them! Let them weigh in on decisions!
- Ask for help. You cannot possibly do everything all the time. Sometimes, asking for help doesn't make you look weak -- it makes people feel like they're needed and a part of the team. When the team can help support you in the way you support them, it strengthens the group.

MAKING IT LOOK PRETTY
Hear what I'm saying and not what I'm not saying. A roleplay with pretty graphics will draw people in, but a roleplay with strong leadership as detailed above is what causes people to stay. For this reason, visuals are on the lowest priority bar despite my deep love and respect for them.

That said, having an eye-catching header, sidebar image, and/or moodboard to set the tone can engage people's interest and spark inspiration. There are often resources in the YWS Trading Post for the less artistically inclined to trade for graphics and visuals you can use for roleplays!

IN CONCLUSION

When it comes to making the roleplay, there are plenty of resources in the Roleplay tab for How to Make a Roleplay on YWS. I'm not here to give you a guide on making one - this is about running one, and hopefully, running it successfully.

Now, you may be saying: sound, you're taking this way too seriously! Storybooks and roleplays are just for fun! To which I say: of course! But why only just? Sometimes fun is found in the full-send. Sometimes fun is found in taking it seriously, and aiming to do it with excellence! If that sounds like you, then maybe you'd be a good DM. Or, maybe you're just the writer a DM is looking for.

Yes, sometimes things don't work out. Your friends (said writers) are human beings with their own lives. Life will always take priority over voluntary group storytelling. But there are people out there who will prioritize storytelling because they love it. Some people will make storytelling a part of their life because they have an unending itch to write that will not leave them if it is not scratched. Those are the friends I, at least, try to find.

I hope you find them too, and I hope you find the courage to DM a story you've been itching to write.

Still Have Questions?
Ask them here. I don't have all the answers, but I'm down for the hard, the cutting, the practical, the sincere. I'll do my best with what I have to offer!