Team building planning timeline

A workshop for twenty people can be booked in three weeks. An offsite for two hundred is a four-month project. The timeline below is for a typical half-day for 30 to 80 people; shrink or stretch it to fit, and generate a dated version with the timeline generator.

8–12 weeks out (4–6 months for 100+ or an offsite)

• Agree the objective in one sentence: mixing new people, breaking silos, or a reward. Then the headcount, the date options, and the budget per head. Check the budget against the CRA rule: a social event open to all employees at $150 or less per person including taxes stays a non-taxable benefit; above that, the whole amount is taxable.
• Pick three dates and check them against company deadlines, school holidays, religious observances and the long weekends. Tuesday to Thursday afternoons get the best attendance; Friday afternoons get the best mood and the worst attendance.
• Decide the format by team size using the activities page, and shortlist two or three venues or providers. For June and September dates, book now; activity venues and breweries fill their weekday afternoons weeks ahead in those months.
• If outdoors in a Toronto park or ravine, apply for the Parks special event permit; summer weekend permits need months of lead time, and even a weekday group activity needs a permit if it involves equipment, catering or amplified sound.

6–8 weeks out

• Confirm the venue and the provider in writing with the headcount range, the start and end times, the activity, the room set, what is included and the cancellation terms. Ask for a certificate of insurance from any outside instructor or performer.
• Book the host or facilitator for groups over 25. Send them the objective and a draft team list; mixed teams assigned in advance work better than self-selection on the day.
• Decide the meal: in the venue, catered in, or a restaurant afterwards. Book the private dining room now if it is a restaurant.
• Draft the alcohol policy. Licensed venue: choose a drinks package or a ticket system. Unlicensed space with your own bar: apply for the Special Occasion Permit at least ten days before, and arrange Smart Serve-certified servers.

4 weeks out

• Send the invitation with the date, place, start and end times, dress and footwear, what the activity involves, and a form that asks about dietary needs, accessibility, sensory needs and whether the person prefers to sit out physical elements. Make opting out of a physical element easy and private.
• Arrange transport if the venue is outside walking or transit distance from the office; a coach for 50 is cheaper per head than reimbursing taxis and gets everyone there at the same time.
• Confirm the run of show with the venue and the provider: arrival, welcome, activity blocks, meal, close. Use the run of show template.

2 weeks out

• RSVP cut-off. Give the venue and caterer the number and the dietary list, coded by person for a seated meal.
• Finalize the teams and the team names. Brief managers on their role: participate, do not run it, do not judge.
• Order any branded items, prizes or materials. Prizes should be small and funny rather than valuable; a trophy that lives on a desk outlasts a gift card.
• Walk the venue if you have not seen it. Check the step-free route, the washrooms, the quiet space and the sound level of the room.

The week of

• Confirm every vendor by phone. Print the vendor contact sheet and the run of show.
• Send a reminder with the address, the transit directions, what to wear and the start time. Remind people that the activity is optional and that the meal is the point.
• Pack the day-of kit: name tags, team lists, a first-aid kit, phone chargers, spare water, the survey QR code.

The day

• Arrive an hour early. Set the welcome table, test the host’s microphone, confirm the dietary plates with the kitchen.
• Start on time, even if people are still arriving. End on time, especially if people have childcare.
• Take photos only with notice: a line on the invitation and a sign at the door, and honour anyone who opts out.

After

• Within 48 hours: thank-you note with three photos and the two-question survey. Pay the balances; tip the host and instructors where gratuity is not already on the invoice.
• Within a week: read the survey. Above 70% yes on both questions means repeat the format; below that, change the format before the venue.
• Within a month: record the cost per head and the attendance in the ROI calculator for the next budget conversation, and book the next one; teams that do something every quarter get more from each one than teams that do an annual blow-out.