Group logistics: the unglamorous part that determines everything
A retreat has a headcount problem that conferences do not. By the time merchandise is packed, the list has changed. Someone added a partner, someone dropped out, someone who was optional has turned out to be essential, and the intern nobody mentioned is now on the programme. The standard failure is one per confirmed attendee, delivered in advance, with no spares and no way to add someone on the day.
Collect sizes and names in writing, early. Ask for a name, a garment size where relevant, and anything the person has told you they would actually use. This is the only way to avoid a wrong-fit garment at an event where the recipient cannot return it and does not want to hand it on. Set a deadline for the list and treat it as fixed, because the production window closes well before the retreat does.
Order spares deliberately. A small number of extra sizes, including at least one of each of the common sizes and one above the largest on the list, absorbs the dropped meal, the extended stay, the colleague who brings a partner and the damaged-in-transit item. The cost of a spare is trivial; the cost of a participant arriving and finding nothing is not, particularly at a residential event where everyone is watching.
Plan the delivery point. Items distributed at a table in a common area are fine for identical giveaways and wrong for personal gifts. For gifts, the practical options are delivery into rooms before arrival, or holding everything and presenting at a scheduled moment. Both need a named owner, a place to store the items and a method for knowing which ones are left, because an unlabelled box in a corridor at a residential venue is how a well-run retreat ends up with gifts delivered to the wrong rooms.
Label by person, not by size. If items are delivered into rooms, each must carry the name of the person it belongs to. Labelling by garment size or by group guarantees a distribution problem when people of the same size are in different rooms.
Decide the last-minute solution. Someone will not be on the list. Decide in advance whether the answer is a spare from the buffer, a small second run held locally, or nothing. Doing this during the retreat, at a distance, with a deadline the next morning, is how a small logistics gap becomes an expensive one.