For one of my campaigns I have a characters who is the leader of his own mercenary company. The problem is every time he tries to perform leadership, he winds up rolling against his followers discipline which they have a skill in meaning he has to roll against a challenge die relatively often and has lead to several hilarious moments when he despaired and succeeded but leads him to be upset that he still winds up suffering for rolling a check on friendly NPCs. I kinda though adding boost die to show that they are willing to be lead. I don't want him to just do the ability without a roll as he invested in the skill specifically so he could act in charge

I guess my problem is do I treat trying to perform leadership on an ally as an opposed check or just treat it as a regular check and determine difficulty without accounting for the NPC's willpower or ranks?

Why not use the challenge or odds that the company is facing as the difficulty instead? That way the mercs will be less likely to be inspired if they are about to go up against a massive force rather than just another merc crew.

You might find the fear table helpful.

Highly-disciplined followers should be *better* at following orders, not worse. Leadership vs Discipline seems like it should be used when you're trying to take charge of a ship when the captain's just fallen sick, or you're trying to raise a mob in a frontier town.

Yeah - Leadership v. Discipline seems to be the roll for taking command of a group, not the roll for leading a group you are already in command of. I agree with Fang that rolling against the difficulties listed in the Fear column might be the best, to represent inspiring them to overcome their hesitation, or act against their first instincts.

I also wouldn't ask for a roll unless it's something out of the ordinary for the company.

Highly-disciplined followers should be *better* at following orders, not worse. Leadership vs Discipline seems like it should be used when you're trying to take charge of a ship when the captain's just fallen sick, or you're trying to raise a mob in a frontier town.

I don't disagree at all, but I had to comment anyway just from reading your nick...

I don't want a croissant, bagel, toast, crumpet, rolls, or anything else even remotely bread related.

I love that show.

If its plain stuff that the group would be used to, just handwave that they follow the order, no check required, thats what I would say. Otherwise, the fear table is your friend! Use it