Tricking Your Players Into Making Great Characters
I love a great story.
It's why I love being a dungeon master and running games.
So why do I always get to a point in every campaign where I get bored? A point where I don't have any drive to keep writing adventures?
I realized my problem: I stopped caring about the characters. Don't get me wrong, my players are awesome: this wasn't their fault at all. The characters become stale to me because I never encouraged them to change and grow—the very essence of great storytelling. I didn't even tell them that I wanted their characters to change and grow.
But being a player shouldn't require you to be a talented writer. I'm not going to start doing presentations for them on three-act structure. Being a player should be easy and fun. I needed a way to get them to make characters I cared about, but I didn't want to lecture them.
So I decided—I needed to start tricking my players into making great characters. And it was the best decision I ever made. (Hopefully my players will forgive me one day.)
What Are "Great Characters" and Why Do I Need Them In My Game?
Let me be clear: most characters are good. "Tony III", the barbarian that speaks in grunts and axes anything that moves is a good character. If he wasn't good, no one would play him.
But good characters aren't good enough for me. I need great characters.
I need turmoil; inner demons; adversity. I need characters that I lose sleep over. I need to be dying to know what happens to them. I need to be on the edge of my seat wondering what they'll do next.
I need to care about them.
And remember, I don’t want to make anyone feel like they are doing something wrong. I need to communicate this with subtlety. I need to get them to do a few things without me issuing arbitrary commands.
The problem reminds about learning to conduct a band when I was in university. It's a unique situation where you need to relay a ton of information with very little effort. You can't stop and tell every player and section exactly how loud they should be how slow they should play. So you learn little ways of tricking people into doing these things using small gestures and body language.
I wanted to find the right tricks for encouraging character development. I’ve discovered that some very simple prompts can create an endless amount of ideas. And that's what being a dungeon master is all about: doing the least amount of work for the biggest payoff. I'm already busy. I don't have time to read through five-page backstories, and my players don't have time to write them.
So here are the best ways I’ve tricked players into creating complex, awesome, gritty characters:
I'm clear about what I want.
I ask the right questions during character creation.
I make the game incredibly challenging.
I make rests work overtime.
I force them to come to terms with character death.
Sound weird? Great. Let’s dig in.
Tell Them What You Want
It's been said a thousand times, but here it is again: dungeon masters are players, too. We should have fun. Even though we have a little more work to do, it's still a game.
When I get my players together to make characters, I always ask them, "What do you want this game to be?" Then I write down all their ideas. Someone wants a lot of mysteries to solve. Someone else wants to fight a dragon one day. It all goes into my notes.
I do it because when we're all sharing an imaginary world, it’s important that everyone cares about it. Everyone should get something out of it that makes them want to come back every session.
But how often do you tell your players what you, as a DM, want?
I know this one's simple, but some of us are prone to putting the needs of others on a pedestal. It can feel like the players are doing you a favour, indulging you in your little make-believe world, so you make everything about them and their desires.
But your opinion is important. We put in tons of work, and players see all the effort you go through: planning games, writing stories, picking up snacks. So don't be afraid to ask for something in return.
No matter what they want, I'm crystal clear about what I want, too. I tell them that I don't care if they want to play loners or drunks or secretly-evil characters. But their characters have to be interesting, and to me, that means they need the potential for change. Their characters have to develop over the campaign.
When I tell them this, it gets them thinking beyond who their character is: they start thinking about who their character could be. If they have an awesome, powerful idea for their character, they might start thinking about where their character starts off. Then they can play to find out how they reach that potential.
Again, it's simple, but most players never get that far without a prompt. And there’s a good reason why.
Characters level up, and when they do, they get new spells and abilities. Mechanically, they have to change. It’s in the rules. But there is nothing in the rules that says characters have to change as people. I have to ask for that. There's no backup. No page to reference. Just me.
The first step to getting players making great characters isn't even a trick—it's being direct and honest with them. If you try anything in this post, try this first.
Three Simple Questions
Many role-playing games are about telling engaging stories, in some way. But they tend to assume great stories just happen.
Storytelling isn’t natural and intuitive. If it was, everyone would be a best-selling author.
So I add to character creation a bit. I ask questions that give their characters more potential for growth. Because personality traits and bonds and ideals (what's the difference between all these again) won't cut it. They are static, unmoving. And often, they’re forgotten the moment they’re written down. That’s what happens when you add something that has no mechanical relevance to a game that’s already overwhelmingly complex. It gets ignored.
For the characters I want, they need more. If a character is going to change over the campaign, they need a few things. They need to be a part of the world around them. They need some emotional levers I can pull. They need a little bit of history. And they need to be a bit incomplete so they have somewhere to go.
You might come up with your own questions, but these three cover what I need. After I'm done, I'm left with a bunch of ammunition. The rulebooks give you the ammo to make the game mechanically challenging, like monsters and traps. I'm gathering ammo to make the game emotionally challenging. For the characters, at least. You'll see why this info is so important further down.
Question 1: Who are the people they care about the most?
A lot of story-focused role-playing games have begun to use a character's friends and enemies in the very mechanics of the game. D&D doesn't. Which is fine, it’s still a great game, I’m still playing it. Unfortunately, this leads to a lot of orphans and loners who have "trusts no one" scrawled on their sheet somewhere—characters with no chance of developing and because they don’t care about anything enough to change.
A great character needs to be connected to the world around them, and the best way to create that connection is through people. Asking about who they would risk their lives for reveals a lot about them.
I don’t let them answer, “no one”. If they only care about one or two people, that’s fine, but I like to remind them that people with very few friends tend to be incredibly dependant on them. When all that connects you to the world is one person, that person will mean the world to you.
When you write down their answers, you’re given a list of NPCs you can threaten to raise the stakes. When I introduce them in the game, I say something like, “How have you changed since you last saw them?” and have the characters react to that. Sometimes the loss of a loved one—or even the betrayal of one—is enough to change a character forever.
Question 2: What was the first book in your series?
I learned this one from running a game of Fate Core and it always catches players by surprise. Most players think they need to make characters that suddenly wake up and find out they’re an adventurer. They assume everyone's meeting in a tavern for the first time, ready to fight their first goblin.
I push them to think about their characters as people who have already learned some lessons and lived a little.
When I ask this, it makes them think of their characters as people who have gone through some kind of change already. This means they are much more likely to continue to change, which is exactly what I want.
It also gives them permission to be a little badass. Sure, it’s fun playing the chosen one that was a simple farm boy until he uncovered an ancient sword last week. But I find this starts characters off feeling weak. Even 1st-level adventurers are above and beyond the average characters: they should already have a bit of experience by now.
For bonus points, I ask them how they met the other player characters: who saved whose life, who's got a score to settle. It's hard to start a good story with a bunch of strangers. You can even ask these questions in the middle of games to add some flashbacks and drama.
Question 3: What’s a weakness your character isn’t aware of yet?
This is one of my favourites. Flaws are fine, but many truly great stories are about a character discovering their flaw before having to face it. This question forces players to think of their characters as incomplete.
It also has a secret benefit many don't realize: it puts a wall between the player and the character. You might think that sounds negative. But often the culprit of a flat character is a player that rarely considers their character as a separate entity. People tend to change very slowly. If their character is just a mirror of themselves, the character will take years to develop.
When you ask this question, you’re really asking, what do you know about your character that they don’t? It gets them thinking about the differences between them and their character. And it gets them thinking about how they’ll discover this flaw—a point in the story where that character’s guaranteed to grow.
It's only one question, but it does so much work for me. It sets up a lot of drama in the future, and it puts the player in the passenger seat, so to speak. For great characters to develop, the player needs to be a puppet master—watching the character from a distance, pulling the right strings at the right time.
Make Them Sweat
Here's a confession: I only run hard or deadly encounters. No easy ones.
As a dungeon master who leans into narrative more than combat, this surprises people. But good stories need challenges, and I make those challenges difficult.
Why? Because the best games we play are where the characters are all proud of what they've accomplished. When players are saying, "I can't believe we survived!", they're always grinning ear to ear.
If you’re worried about not having enough variety, remember that your campaign doesn't have to include every little thing the characters do. Great serial TV shows don't include every day of someone's life. When you watch Star Trek, you see the highlights. You see the times where they almost didn't make it. If you're only playing 2-4 sessions a month, make them count. Make every game an episode you want to watch.
Remember when I talked about the ammunition I was gathering earlier? The rules give you every tool you need to make combat and exploration challenging. But if you want to make the narrative challenging, you need to gather your own ammo and raise stakes.
Use everything you can. Do they have loved ones? Put them in danger. Do they serve a knightly order? Threaten to kick them out. Do they come from a sacred forest glade? Start a fire.
It's cruel, yes. But these are the challenges that change your life. And the more intense the challenge, the more effective the next tip will be.
Putting Rests to Work
I have a technique I like to call “gathering by the fire”. This gets into story pacing a little bit, but I don’t want to get carried away. Here's what you need to know: great stories have climaxes and rising action, where things get more intense, interspersed with calmer moments where the action slows. Like a rollercoaster, the most intense moments are sometimes the slowest, right before you plummet.
D&D is great at creating rising action. But what mechanics slow things down? Rests! Often resting involves tending to wounds and deciding how to split up treasure, but I like to add a little more to them. It's simple and low effort, and it can go along way.
I go around the table and ask each player to describe how their character unwinds and reflects on what’s happened recently. If they’ve overcome a tough combat, are they proud? Exhausted? Are they retelling the story around their campsite even though it just happened? Are they adding a notch to their blade?
If they went through an ordeal that brought up their beliefs or revealed a weakness, I’ll ask them about that too. Sometimes a rest can turn into a full-blown scene in itself. Sometimes it might be the best scene of the entire session.
So take a moment and let them roleplay a bit. They might interact with each other, or they might do something on their own. Make sure everyone participates. It's like a warm-up or practice session: if they get used to thinking in character during these calm moments, they'll have an easier time doing it during more intense scenes. These moments might be the only chance for the other players to see the growth that makes each character so interesting.
Very important note: sometimes rests are not safe. If you are planning a surprise ambush or dangerous event to occur, don't trick them into acting in character then punish them for it. I flat-out tell them: you're safe for a bit, nothing will happen. They need to feel comfortable. If you must include some kind of danger, separate it from the roleplaying part. Tell them it's safe while they act things out, then give them a chance to return to their tents or get back to camp before the action starts. Don't betray their trust.
No One Lives Forever
I make a habit of asking how players think their character’s stories might end. Many players fear character death like it’s some kind of failure or game over screen. I like to get them used to the idea that characters retiring can be a positive thing.
It makes them think about what their character has to go through to get to the end of their story, and might give you a lot of material for adventure writing. They don't need to decide what's going to happen and write it in stone. But it's good to think about the possibilities.
Some of the best advice I've read about running games is from Dungeon World, which is: play to find out what happens. When everyone's doing this in unison, you can make some really incredible stories.
You don’t need to know if the elven wizard is going to sacrifice their talents to save their people or be driven mad with power. But you might figure out that they’ll be confronted with that choice. Don’t decide the outcome, but ask them what they want their character to face. Discovering how it all plays out is the best part.
But Isn’t Death Part of the Rules?
Some people like to use death as a punishment. That's fair, it's in the rules, and it happens in my games too.
But resurrection is also in the rules, so the choice of when to stop playing a character is entirely up to the player. Want proof? Watch a player make four generations of Bob the Fighter after getting killed every couple of sessions.
I let them know death isn’t a failure: it can be part of a great story. I also tell them their character doesn't have to die for them to stop playing them. It seems like common sense, but most players never consider it. Characters can retire, lose their mind to madness, or sail off on a journey of their own.
This can spur everyone to think about new characters. Everyone goes through a learning phase—especially new players. Sometimes a character is great for five levels, but then you realize what you would like to do differently next time if you had only known better. Let them know new characters are welcome. They often add a lot of new story potential for the other characters, too.
Here are the tips laid out again, short and simple:
Be clear and honest about what you want.
Ask the right questions during character creation.
Make the game challenging.
Use rests to prompt role-play.
Make them think about how their story ends.
This advice isn't for everyone. If you're like me and have a burning desire for complex characters and satisfying story arcs, then sure, use it all.
Maybe you found a few bits and pieces you like. That's okay too. Most of it works well on its own to add a little something to your game that it might be missing.
If you’re looking for games that help inspire great character moments, I recommend you take a look at Dungeon World (specifically the rules about bonds and the GM moves), character creation in Fate Core, and beliefs in Mouse Guard RPG.
What do you do to help players make great characters? Have you tried anything here before? Let me know in the comments!