Slaves to the Dice

When you roll dice as the game master, you don't ever do it while expecting a certain result. When you call for a roll from your players it is no different. 

Unfortunately this is not a universal policy. I have participated in a convention game where the DM kept calling for skill checks for the group to overcome a certain challenge. There was no consequence for failure, but he kept calling for rolls anyway. After a couple minutes of laughing and joking our way through the repeated failures, boredom set in. A silence fell over us all, filled only by the sound of plastic polygons clattering across the tabletop. It was like some grim ritual as we waited for the dice to provide us with the right numbers to free us to adventure again. It's times like those that remind me why tabletop gaming often gets the short shrift as a mainstream activity. That sort of monotony is unheard of in other media, and misses the basic concept of entertainment as a whole.

Dice rolling doesn't need to impede your progress, and you don't need the dices' permission to advance. Rolling doesn't do anything but create a branching path of outcomes, and if the eventual outcome will be identical regardless of the result, it has no point. 

And then there are the worse cases where a roll is called for when performing a simple action, like ordering a drink from a bartender or tying your horse to a post.

 Remember the message you are sending when you call for a roll. A roll doesn't represent a character's action within the fiction, it represents their risk of failure. It represents danger. At the very least it represents the chance that things won't work out as well as you planned. 

Critical Success and Failure in MY Game? It's More Likely Than You Think.

In many systems, rolling the lowest value has extra serious consequences. Critical failure, botch, whatever you want to call it. But in most systems, it is not that unlikely an event. In a D20 role playing game, that's one in twenty chance. That makes it so much worse if it is applied to basic and everyday actions. 

Don't turn your bold adventurers into this guy.

If every single time you used your car there was a one in twenty chance of being involved in an accident, you'd soon find yourself taking the bus everywhere. So it is with dice rolls to determine success at basic out-of-combat actions like climbing a tree, dancing a jig, or taking their dire badger for a walk. Your players will stop taking decisive actions if they are afraid that the most basic move might result in a negative consequence. It's like being trapped barefoot in a room of broken glass, your players are just going to end up stuck in a corner or tiptoeing around at a glacial pace. Or worse, it becomes a comedy of errors with characters randomly tripping over their own feet and causing mayhem when they attempt to accomplish anything.

Conversely, don't ever tell a player to make a roll and deny them success even if they roll the highest value. It's deliberately misleading the player into thinking they have a chance of success so you can pull the rug from under them, and watch their shock when a critical success is denied. If an action is impossible, it does not need a roll. Your players should always be considered a friend. And you shouldn't play those kinds of tricks on your friends, it just ain't right.

In the heat of combat, of course, things become more difficult. That's when a character is under pressure and will often need to roll for actions that would usually be easy to perform. This principle applies to non-combat scenarios too. If the character is under pressure, and there may be consequences for failure, it is time to start chucking dice. Let's put it this way: making yourself a sandwich is routine, but making a sandwich for the Crown Empress will require a roll, and the player had better hope it's a good one!

There are always those few instances where failure is inevitable.

Routine Skills, Abilities, and Training

If you want a player to know something, then don't require a skill check for it. Instead, look to the earliest writings of Dungeons and Dragons for inspiration on how to handle these things. In some of the early modules, such as the Isle of Dread, there are scenarios in which a player character of the thief class has the ability to navigate certain hard to reach locations regardless of their statistics. Why? By virtue of their basic training as a thief, of course.

Computer programs often have features that work by triggering automatically if the conditions are met. "IF/THEN" statements, or conditional statements. This provides a great framework for how we treat player characters. If they ask to do something that would help to progress the game, don't play dice with it. Instead of rolling the dice on vital information or basic actions, first determine if that player's class has training or specialization in the skill. Then treat it as a 'routine' action, one that doesn't require a roll. The player has passed a 'gate' by having the proper skill. They still get to perform their role in the game, practicing their specialty, and you have encouraged them to use their skills rather than fear them.

This way you can plan adventures and scenarios around the characters in your party. A thief may already know of a local smugglers' guild, and a wizard may notice a spy using a common disguise spell. These things can happen by fate rather than chance, paving the way for the story while showcasing the unique skill sets of the PCs.

How do you know the difference between a skill check that should be routine and a skill check that needs a roll? Here are my general guidelines when making that call:

View this table as an image here.

One Last Note

One of the worst thing any dungeon master can say is "Oops." It makes everyone nervous and damages your own confidence. Though it happens to the best of us, we can prevent a lot of oops moments by remembering not to let sheer chance undermine your game. No DM should feel like they are a slave to the dice. They aren't artifacts of power, or sacred stones of fateful import. They are gaming aids to keep things lively and exciting. Your main tools are still your knowledge of the rules, creativity, and of course your own awareness of your players!

Happy ventures!