December is when teams look back, and January is when they commit to what comes next. A year-end planning retreat does both in one trip: a day on what the year actually delivered, a morning on the three or four things next year is for, and a dinner in between that doubles as the holiday party. This is the format we see work, whether it is a leadership team of five or a company of forty.
Before you go: bring the year with you
The review day only works if the facts arrive with the team. Two weeks out, ask everyone the same three questions in writing: what went well, what didn’t, and what we should stop doing. Collect the answers in one document and read them before you leave, so the room spends its time deciding instead of discovering.
- This year’s numbers against this year’s plan, on one page
- Last January’s priorities, word for word
- Everyone’s three written answers, gathered in one document
- The decisions that stayed open all year, listed
- Who owns next year’s budget, and whether they are coming
Day one: what the year actually did
Spend the whole first day looking back, and resist the urge to start planning before lunch. The great room stays set up for the entire stay, so the scorecard you put on the wall in the morning is still there when you need it on day two.
- 9:00 — The scorecard: plan against result, read out without commentary
- 10:30 — What worked, and why. Name the people behind it
- 12:15 — Working lunch at the dining table, which seats fourteen
- 1:15 — What didn’t work, said plainly
- 2:45 — What to stop: the projects, meetings and reports nobody would miss
- 4:00 — Done for the day: the hot tub, the games room, or the ten-minute walk into the Village before dinner
Stop at four even if the list is not finished; the gap before dinner is where the day settles. Some people head for the hot tub, some for the ping pong table in the games room, and some walk into Blue Mountain Village for a coffee and the shops. The conversations that start then tend to be the ones that fix tomorrow morning.
The evening: the year-end dinner
The night between the two days is the holiday party. A private chef cooks in the chalet, or the team walks ten minutes to the restaurants in Blue Mountain Village; there is no per-plate minimum, and you pay the chef or the restaurant directly. Chefs and caterers, with their phone numbers, are listed under private chef and dining. Toasts at the table, then the hot tub or the games room for whoever is still up, and nobody drives home. If the party is the main event, see a year-end party at the chalets.
Through the holidays Blue Mountain Village is lit up for its Holiday Magic season, this year from November 20 to January 3, which makes for a good walk after dinner.
Day two: choose what next year is for
The second morning is short and has one job. Choose three or four priorities, not ten, and give each one an owner and a first step.
- 8:30 — Breakfast in the chalet kitchen
- 9:00 — Next year’s three or four priorities, chosen from yesterday’s lists
- 10:30 — An owner for each, and what happens in the first 90 days
- 11:30 — What we are not doing next year, said out loud
- 12:00 — Lunch, then the rest of the day is yours
The retreat does not have to end the moment the last decision is written down. Checkout is agreed when you book, so lunch can be a long one, and the afternoon can go to the area: Blue Mountain Village is a ten-minute walk for coffee and the shops, the Scandinave Spa and the Scenic Caves are a short drive, and Collingwood and Thornbury are fifteen minutes away for a late lunch or the harbour. In ski season the hill is 500 metres from the door. Not everyone is heading back to Toronto, so let people wind down and leave when it suits them; see things to do for the full list by season.
December or January?
December closes the year while it is fresh and lets the dinner double as the holiday party. January works better if you want final numbers in the room, and the same two days become a kickoff; see a sales kickoff venue. Either way, midweek dates are the easiest to secure, and the holiday weeks go first.
In winter the ski hill is 500 metres from the door, so a third night turns the afternoon of day two into a few runs. Blue Mountain plans to open for the season in mid-December, weather permitting.
Sizing it
- Five to fourteen people: one chalet, every session in the great room and everyone at one dinner table
- Fifteen to twenty-eight: two chalets side by side, a working room in each and two long tables for dinner
- Up to forty-two: all three chalets, with a great room in each for parallel sessions
- Colleagues who can’t travel: the wifi holds a full day of video calls, so they can join the scorecard session
The planning checklist covers the logistics, and the two-night agenda is the same shape for a general offsite.