Dungeons & Dragons (4ed): Dungeon Master’s Guide - Tips & Strategies

When running skill challenges, it is important to keep an open mind to how skills may apply to a given situation. As with many RPGS, players tend to specialize their PCs, which can lead to PCs that are very good in one thing and very bad in another, or to skill sets – especially the social skills – that are only really used by a minority of PCs.
Skill challenges that use a specific set of skills may not be fun for everyone – as they may exclude players who do not wish to be the one that ‘loses’ a challenge.
There are a few ways to circumvent this.

1. Be flexible how you apply skills. I.e. making people aware of real risks can well be done with an Intimidate check without being threatening (‘if you folks stay here in the village an avalanche is going to come down on your heads when the snow falls’), and a Thievery check may be used to perform an entertaining trick (legerdemain). Put the intiative with the players, so it allows them to play to their PCs to their strengths.

2. Allow a minor bonus on clever use of a skill or good roleplay. This lowers the risks players may feel when using untrained skills.

3. Allow supporting roles (seconday skills) that do not cause failures but may aid other PCs earning a success, either by a minor bonus or a small in-game benefit. This draws in players whose PCs are poor in a skill.

4. Failure is not bad, as long as losing is spectacular or at least entertaining enough. If a failure leads to another adventure or a side quest, it can add to the fun, and it will reduce the aversion of players for risky situations.

5. Do not make the challenges too easy. If all skill challenges can easily be won, especially by the same highly skilled PCs, they are no fun either. There generally has to be some risk in a challenge even if a PC has his skills maxed out. Losing the challenge should be an option.

6. Fit the challenge to your players and their PCs. Use NPCs they love (or love to hate), situations that intrigue them or offer rewards that they actually want. Make sure they do not see the encounter as a numbers game.

If you use a ready-to-go skill challenge from a published adventure, these may not take the above into account (especially older ones, which were written when the idea of challenges was new). In those cases especially, do not fear to deviate from written text and apply the tips above.