1) So I'm a new DM and I feel ok about mostly everything (my players always have feedback about what did and didn't work for them and I take that seriously if it's within my ability to fix) My big issue is 2 of my players have to be hounded to get to participate. We've all agreed to meet once a month, but these two won't help find dates and won't confirm dates that others have proposed unless I ride their ass. They don't participate in our group chat or our group calendar
“2) I told everybody to have a backup character last session in case they died, and to email me the details a week before the session so I would have them. By the day before, I had everybody’s but these two. I’ve tried bribing/rewarding, penalties and the only thing that seems to work is just riding their ass butI have enough work getting these sessions together, y'know? Is it ok to sit them down and tell them they either step up their game or leave the group? Or is that too harsh a response?”
I’ve personally never had this problem (I am very lucky in this regard), but my heart goes out to you. It’s a fairly common experience among gaming groups. I talked to my friend who is running a once a month game, and it’s had these problems in the past. This is what he told me:
“This game comes with homework. To really get into it, you need to do some preparation outside of the game-day itself. A common misconception is that it’s the DM’s job to organize everything, but if everyone wants to participate, they should contribute some effort. If you have the balls to tell those players to shape up or leave, then you should do it.”
He’s also had some luck with delegating certain tasks to his players. A couple players are currently in charge of coordinating the schedule, and another coordinates food. This leaves him free to focus on planning the session without getting overwhelmed.
Putting gendered language aside, I largely agree with his advise. The only thing I might recommend is starting that uncomfortable conversation by pointing out to them that it seems like they don’t really want to play your game. They need to understand that you want them to be a part of your group, but not if that means constantly having to nag them to get things done.
Thanks for the question, and good luck!