First Off, Decide on the Length of Your Company Retreat

The duration of a retreat will vary depending on what the team wants to get done work-wise, the budget available (and how much you're willing to spread it out), and the amount of time you want to set aside for activities and leisure - but there are other factors to consider when figuring out how many nights you want to make your next retreat.

First and foremost the organization must be respectful of each attendee's personal lives, particularly those with families or young children at home. For this reason, we recommend avoiding overlapping into weekends when possible and obviously trying to steer clear of major holidays and/or religious dates. Also worth considering, with the entire team on the retreat, not much work may be getting done in the office so it's best to get to the point and stay focused! This should be balanced with the fact that it takes longer for some than others who are coming in from farther away, and adjusting to the local timezone or schedule will be different for each individual.

How to Structure the Retreat | Creating a Good Balance

After planning these types of trips for years, our experience has taught us the most efficient trips are usually around 5 days in length. This allows for enough time to 'settle in', allocate a reasonable amount to getting work done, and leave enough time to include activities, excursions, and leisure time to give the group ample opportunity to explore the local culture and also get to know each other better without a structured agenda.

Below is a sample 5 day itinerary that we have found the most effective for our clients who have people coming in from further abroad (particularly remote companies) who also want to keep work & meetings as the focus of their retreat:

  • 1 day allocated to travel
  • 3 (full) days of work
  • and 1 day set aside for “fun” activities or leisure time and team bonding

This won’t keep mom or dad away from the family for too long but also isolates the team long enough to really dig in and make meaningful connections with each other. Anything less can feel rushed, while anything more can drag on or begin to interfere with personal commitments, so stick to 5!

Company retreat in Honduras
Working outside of the office can often spark creativity

Day 1 (Arrival Day)

The first day is going to be allocated to scattered arrivals, with not much in the way of structure or planned content outside of a team-wide event in the evening. This also gives everyone the whole day to get to the destination, ample time in the afternoon to catch up with colleagues (or catch a quick nap!), but still brings everyone together with an anchored full-group event that will bring everyone together. Ideally, aim to have nothing formal planned throughout the day until a Welcome Reception to gather everyone in the early evening, and leading right into a full-team dinner. Don't plan too much for after, as some will be jet-lagged and want to get to bed early, and you don't want to create a sense of F.O.M.O for anyone!

Company retreat in Tuscany
Welcome Reception in a Castle Garden in Italy

Days 2-4 (Work Days)

The next 2-3 days should be prioritized for work and strategy and ideally follow a similarly structured schedule to the company's average work-day in terms of start and end times. Kick things off with a Welcome Address by the CEO/Founder after breakfast on the first work day, and make sure to include some Housekeeping to cover expectations and general admin items like wifi passwords, location of washrooms, standards for conduct (particularly with alcohol), addressing cultural differences in regards to humour and personal boundaries, and anything else you think is worth bringing up. Allow some time for questions in a 'town hall' format.

For the rest of the work days, make sure to mix full-team sessions with department/group-specific ones to give organizational teams some dedicated time to tackle ideas or issues they may not often get the chance to talk about face-to-face. Break often, give extra time for lunch (to allow people to call home, or introverts to recharge their batteries) and aim to wrap up in the mid-afternoon on days where no offsite excursions or team-building activities are planned.

Break often, allowing people to call home or for introverts to recharge.

Most groups like to sprinkle in a walking tour earlier in the week to acquaint people to the destination and orientate themselves, and try to offer a company-wide team-building activity in the first couple of days to offer the chance to familiarize everyone with new faces. Save the optional activities where the team split up into smaller groups with more interest-specific activities (cooking classes, history tours, etc.) for the end of the retreat when the heavy lifting has already been done and it's more about savouring the destination than the group experience.

Company retreat in Eastern Canada
Work Sessions at a retreat on the Eastern coast of Canada

Days 5-6 ('Fun' Day & Departure)

The final day (or one wedged towards the end of the week) should be left completely wide open - with either unstructured leisure time or very loosely organized games (e.g. Volleyball Tournament, Settlers of Catan, etc.). Often the organizers or a CEO will feel compelled to try and cram in as much as possible (after all, you're paying for everyone to be there, and its technically a "work day"), however we've found the counter-intuition is usually the best way to go. Having completely open time is often when the best memories and laughs are shared as people will naturally gravitate towards hanging out with coworkers or talking about some side-projects or ideas they have that didn't necessarily fit in earlier in the programme. You'd be surprised how many new products or services (or planned visits) come out of this 'free' day!

It may be counter-intuitive, but keeping the last day completely wide-open with unstructured leisure time is often when the best memories are made!

On departure day, don't plan anything. Save this for saying your goodbyes. Maybe consider doing a "Farewell Address" during breakfast, but the likelihood that some team members will have to depart extra early to catch a morning flight means some might miss out. Better save that farewell for a company-wide e-mail, strategically sent when you've had some time to hone your sentiments and maybe add in a few highlight photos from the week to pull on the nostalgic heart strings as everyone boards their plane home and is already missing the crew.

Company retreat in Colorado
Unstructured time is essential to a successful retreat

A Sample Retreat Itinerary

Below is the itinerary from our own internal Moniker retreat, on our most recent edition in Medellin, Colombia in January 2019. We tried to incorporate the same lessons we've seen and learned from observing dozens of clients programs, and emulate a similar schedule with the best pieces we've observed:

Company retreat schedule
The itinerary from our Moniker Retreat, in Medellin, Colombia

As you can see, we followed a similar formula to leaving the first day relatively open to allow for everyone to arrive, settle in, and relax before getting into a bit of an icebreaker and group dinner. The majority of the rest of the week followed a similar schedule - we encouraged morning workouts for anyone interested, with 'Team Sessions' to start and individual presentations called Workshops that followed. The team sessions were organizational groups that jointly presented on how to optimize or otherwise make their workflow more efficient for the rest of the company. The individual workshops were a 1-2 hour session where each person had to present on a topic or run an exercise that they felt would benefit the team or company going forward. Some examples were a brand audit, a workshop on evaluating what tasks in our current roles we like/loved/wished we could delegate elsewhere, and a deep dive into our administrative systems and processes. We left plenty of time for leisure, and incorporated a few local excursions & tours to get us out and about in the city we called home for a week.

In summary, while every team is going to be a bit different in terms of their ideal length of the retreat - starting the conversation at 5 nights and discussing whether more or less time is needed seems to be the right approach. If you're not as concerned with meetings and work sessions, or exploring the city and doing some activities - it could probably be shorter. If your priority is to get some serious work done, or spend time in the destination not feeling rushed - it could probably be longer. The ultimate decision will come down to your objectives, time available, and budget!