Group bookings go wrong for one of two reasons almost every time: dates confirmed too late, or a single point of contact who isn’t actually reachable when a question comes up mid-planning.
Where Most Problems Actually Start
Locking in dates early matters more for a group than for an individual traveller — a hotel can usually accommodate one late change, but ten or twenty rooms shifting at once is a much harder ask, and one that’s far easier to avoid than to fix after the fact.

A single named coordinator, on both sides, resolves more problems before they happen than any amount of paperwork. When a question comes up — a dietary requirement, a room-sharing change, a late addition to the group — it needs one clear person to answer it quickly, not a group email thread.
What to Confirm Early

Payment structure is worth settling upfront: one invoice to a single organiser, or individual payments from each guest. Sorting this out at the start avoids an awkward conversation at check-out when it turns out nobody actually confirmed who was paying for what.
Room type mix is another easy thing to get wrong by assumption. Confirming exactly how many singles, doubles, and any special requests are needed — rather than assuming the hotel will sort it out on the day — is the difference between a smooth arrival and twenty people waiting in a lobby while the front desk tries to rearrange room assignments on the spot.