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Start with the fiction first.
Determine difficulty based on the fiction and circumstance.
For example:
It is a stormy night, and the duke's daughter has invited Valeros (Level 1 Fighter) to a secret tryst in her room.
Player 1: I'm going to look for a way into the lady's window.
It's a dark and stormy night, and Valeros has no darkvision or low-light vision. The GM looks at her notes (or improvises on the spot), there's a tree near the Princess' window. A tree is a fairly obvious thing to find so it's a Trivial Level 0 task (DC 9). It's dark (+1 severity), and it's raining (+1 severity).
GM: Give me a Perception check DC 12 (High Level 0 check)
Player 1:
GM: Great job Valeros! There's a brief flash of lightning, revealing an overgrown tree growing near the Princess' window.
Player 1: I'm going to try climbing the tree!
The GM knows that climbing a tree is a High Level 0 task, again the darkness and rain works against the PC (Severity increases twice to Extreme).
GM: Okay give me an Athletics check, DC 17.
Player 1:
GM: You fail to find any purchase this time. Fortunately the rain and the storm hides the sounds of your frustration, though you know the guard patrol is likely to pass this way soon. You can either try to climb again or find a place to hide before the guards patrol the area.
Player 1: I'll try again.
GM: Okay, a pair of guards approach your position. You recognize them as the ones you met earlier who ushered you into the Duke's feasthall.
"Who goes there?" Says the chubby one.
Player 1: "Oh hello there, it's me! Valeros, that guy the Duke hired to slay those goblins earlier. I thought I saw a goblin enter the keep grounds."
This sounds like a Deception check, definitely not one of Valeros' strengths. These are level 1 guards who are trained in Perception. It's not elaborate or particularly unbelievable (there were goblins in the town earlier after all).
GM: Give me a Deception check, DC 12.
Player 1:
GM: The guards look at you, look up at the window and the tree next to it. One of them rolls their eyes at the other.
"You're not the first adventurer to catch the princess' eye. Get out of here now adventurer and the duke won't have to hear about this, and I won't have to deal with the paperwork of transferring you to the militia cell."
Player 1: I count my lucky stars, and agree to leave.
GM: For sure, you head back to town alone. Thwarted. The princess' attitude towards you will worsen one step, she doesn't take kindly to being stood up.