An NPC Becomes a Henchman
There is no set time at which a player character acquires a henchman. Running
a player character and a henchman together is more difficult than just a player
character alone. Not every player will be ready for this at the same time, so
the DM should control which players get henchmen and when. Wait until the
player has demonstrated the ability to role play his own character before burdening
him with another. If the player does not assume at least some of the
responsibility for role-playing the henchman, the value is lost.
Neither is there a set way to acquire a henchman. The DM must use his own
judgment. Since a henchman is a friend, consider those things that bind friends
together. Being treated as equals, helping without expecting reward, trust,
kindness, sharing secrets, and standing by each other in times of trouble are all
parts of it.
When a character does these things for an NPC, a bond will develop between
them. The DM can allow the player to have more and more control over the NPC,
deciding actions, role-playing reactions, and developing a personality. As the
player does this, he begins to think of the NPC almost as another player character.
When the player is as concerned about the welfare of the NPC as he would be
for a normal player character, that NPC can be treated as a henchman.
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