As we begin to emerge from COVID, plenty of companies have started to consider hosting a corporate retreat again, or those companies who have never organized one, have begun thinking about it for the first time. This is due to a number of reasons; transitioning from an office environment to working fully remote, moving to a hybrid setup, and hiring teammates in far away places among many other reasons. In any of these scenarios, a corporate retreat offers the perfect opportunity to gather the team together to meet face-to-face for the first time, or reconnect after years of being apart in an effort to build stronger relationships and connections within the team.

We understand planning a corporate retreat schedule can seem like a huge undertaking filled with many important decisions; the most significant being deciding whether this is a “work” gathering or mainly a “social” gathering, and understanding the implications that this will have on your schedule. In this article, we will discuss how to plan accordingly for both options, with templates of several corporate retreat schedules covering both styles of retreat and various lengths. However, depending on which framework you believe is best suited for your team, feel free to skip ahead to the relevant section.

Mostly Meetings/Work Focused Corporate Retreat Schedule Templates

For some companies, the biggest value of a corporate retreat comes from getting people together for the exchange of ideas or sharing of new ideas, as many studies have proven this is more effective and long-lasting in person rather than over Zoom. A meeting-focused corporate retreat schedule allows teams to come together and spend time with each other in a setting that prioritizes ‘work time’ over leisure and activities, and generally has a mix of all-hands type sessions and smaller breakout groups with departmental or task-based teams. 

Typically this style of retreat schedule features meetings from after breakfast until mid-afternoon, with less time allocated for team building and group activities, but usually with some evening events with receptions and group dinners to bring everyone together in a more social environment.

Some best practices to consider:

  • Hosting your corporate retreat in a central urban location; a city center or downtown location.  During leisure time between meetings and meals, attendees often appreciate being able to quickly explore or go out for a walk after having spent the majority of their day in a stuffy meeting room with no natural light. Being further removed from the city means free time will be spent on property as there is nowhere to go and this offers less of a mental break from work, as everything revolves around the same space
  • Switching up speakers and presentation format; incorporate both lectures and workshops each day to avoid listening to a rotating cast of speakers talk at the group. This could mean having a morning session where the founder/CEO speaks to the group followed by splitting off into smaller teams and working in breakout rooms to solve challenges the company is currently facing, and then bringing them back to a ballroom for a ‘fireside chat’ or townhall style session. Mix it up! 
  • Provide more than enough breaks; While most hotels will suggest hosting meetings from 9AM-1PM with a 15 minute coffee break, 4 hours with only a 15 minutes off is bonkers! Try to space out sessions with adequate breaks, but do your best to keep the content on schedule and make it clear that you will be starting on time back from the breaks to avoid the schedule stretching on while you wait for the room to fill up again after every break.
  • Host some sessions outdoors (weather permitting) or at least outside of the meeting room. If possible, the addition of natural light goes a long way to improve the headspace and creative capacities of your attendees. Better ideas will come from inspiring settings!
  • Keep things light; encourage your presenters to incorporate some fun elements into their presentations (GIFs, memes, etc.), as 60 minutes straight of slides full of walls of text can weigh down even the most focused and engaged employee. 

Below are some examples of meeting/work focused corporate retreat schedules that we often see in use with the retreats we run. You’ll notice in either scenario the first day always begins much later in the evening (~6PM) with a welcome reception and simple dinner to accommodate the scattered arrivals happening throughout the day. For those who are coming from afar and possibly jet-lagged, avoid hosting too much on the first evening to eliminate any potential FOMO from attendees who want to stick around, but are tired. 

We’d also recommend hosting this first evening on property so those who are tired and wanting to head to bed early have a simple elevator ride or walk back to their room, rather than having to wait around for a transfer back to the host hotel.

[Option 1] 4-Night Retreat Schedule Template

If it’s been a while since your team has gathered or if there are many new faces since your last retreat, we highly recommend hosting a team building or icebreaker activity early in the retreat schedule to help the new faces meet/integrate with the rest of the team. 

This will help ensure  newer team members have an opportunity to meet and connect with others early on and give them a sense of comfort when spotting some familiar faces at upcoming sessions or someone to sit next to at lunches or dinners - helpful when trying to avoid the usual pitfalls of ‘cliquing up’ for teammates who’ve worked together for longer periods together

[Option 2] 4-Night Retreat Schedule:

Consider leaving 1 night free or at leisure so your attendees have an opportunity to explore the destination on their own or if they prefer, stay in and recharge their batteries.

[Option 3] 3-Night Retreat Schedule: 

We highly recommend the second night to be team dine arounds on-site or in town where departments/organizational units have an opportunity to sit down and break bread with their immediate colleagues only–something they may not get the chance to do in a larger, full company dinner

Other things to consider: 

  • Host a full team dinner on the first night and be intentional about seating arrangements. Those who have worked together for a long time will often clique up on retreats and sit with their “buddies”, however, encouraging thoughtful seating charts or going so far as to place name cards on particular seats, will spur new relationships and conversations from the get-go. 
  • Offer activities not centered around drinking (particularly on Night 1). Things like trivia and karaoke can be a fun way to let loose without turning the event into a “pub night” where booze is the focus. Encouraging people to bring their favourite board games from home and hosting a Games Night, or even having an outdoor movie night are some other ideas.
  • Consider bringing in an outside speaker/workshop facilitator; though we understand this may not be in line with your budget as often quality speakers come with a cost of at least $10,000-$20,000, offering a presentation to tie the theme of the week together or to invigorate the audience is a great ‘takeaway’ that ensures people will go home feeling inspired
  • Last full day; we suggest leaving this day relatively light in terms of content and giving attendees a range of options to choose from for optional activities or excursions off site. This offers them the opportunity to explore the destination and local culture or leisure time for those who wish to relax and enjoy the property 

Departure day; don’t plan anything! It is inevitable you will have some employees who will need to leave early in the morning to catch their flights, so you risk excluding them if there is programming. For those with later departures, let them use a day off to enjoy the destination or squeeze in some last minute sights or shopping!

Leisure/Social Oriented Corporate Retreat Schedule Templates

Some companies decide that the purpose of their corporate retreat is less about gathering to work and strategize, but rather more focused on building relationships and a sense of camaraderie which is more easily achieved in person than online. In this case, the retreat schedule will often skew toward team building, group activities, and social events, with only minimal time allocated toward presentations or work.

Best practices: 

  • A good mix of full-team team building activities and down time for people to chill out in their room and recharge or gather in the lobby with their colleagues is a good framework for these types of corporate retreats. It might seem counter-intuitive to most Founders & CEOs hosting the retreat, but in our experience lots of the culture-building and new ideas/initiatives around work actually come out of the ‘free time’, contrary to what you might think! Below are examples of 3 night and 4 night retreat schedule templates that work well to use as a baseline when planning a corporate retreat.
  • Consider introducing a theme or competition for the week that will allow you to divide the group up into teams and bring in a little competitive spirit to the retreat! In our experience, we have found that it’s easier to build relationships in the smaller team setting than in the larger group setting with a cast of 100+ rotating faces. After your kick-off address, start off the day with some sort of team building activity that will introduce colleagues early on. The relationships they start on day one will make the following days a lot easier to network out of their typical work bubble!
  • Be mindful about the level of energy you put into each day. For example, people are usually very excited or charged up on the first day or two which is a great opportunity to host high-energy events like team-building. On nights three-four it’s best to have more low-key events so people can re-charge before the final farewell, which is usually when teams go all out!

As with the more meeting-focused retreats, avoid scheduling anything until ~6PM on the first day to allow everyone to arrive on property without missing out on anything and to give those who arrive early an opportunity to thaw out and explore the property before the festivities begin. Keep this night rather light with a standing reception as opposed to a formal sit-down dinner. Consider hosting on a rooftop to dazzle guests and encourage them to mingle. Plus who doesn’t love a rooftop! 

Center the first morning around having a kick-off session led by the Founder/CEO to formally welcome everyone and jazz them all up for the days ahead. Take the opportunity to celebrate some successes and set clear guidelines on expectations of behavior and participation for the week. Make sure to avoid any gray area about how inappropriate behavior  will be addressed. Remind folks that this is still a work function and should be treated as such in terms of employee conduct. Remember, there are no promotions on offsites, only demotions! 

[Option 1] 4-Night Retreat Schedule:

Host a full-team activity early in the week to familiarize everyone with new faces and to kick things off in spirit! Then later in the week, offer a variety of optional activities in a choose-your-adventure style approach on one day for people to hone in on their personal preferences and passions and connect with others who share their interests. 

Allowing people to tap into their personal interests will bring them together more than forcing them to do an activity that may not be their cup of tea. It is amazing how many times we’ve seen foodies bond around a cooking class table , as they  share their favorite recipes or talk about where they learned to cook! Offering activities that will allow participants to connect with those they have things in common with will give them so much more to talk about.

[Option 2] 3-Night Retreat Schedule:

You’ll notice in both templates one of the middle nights should be reserved for smaller team dine-arounds. Just as it is with the meeting groups, an opportunity for organizational units to spend an evening together without the rest of the company is an opportunity for them to connect with colleagues outside of work and surprisingly, a lot of great ideas have come out of these types of settings. 

In addition to the tips for meeting focused corporate retreat schedules (which also apply here), here are a few more insights we can share after planning 200+ corporate retreats:

  • Leave plenty of leisure time in the afternoons before dinner for people to relax, recharge, or take advantage of the property with friends (old or new). Be mindful that many teams (in particular tech/IT companies) have a lot of introverts on their team, so scheduling down time for them to recharge their batteries or optional events that are less intense (board game night, trivia vs. karaoke party) will go a long way.
  • Stay away from cliché team building events like trustfalls and drum circles (not joking, this is actually a thing we’ve seen). Try to tap into the local scene with things like Amazing Race style events that get the team exploring the town or outdoor activities (Beach Olympics, Highland Games, and Tournaments) where possible.
  • Costume Parties! Most teams enjoy a good reason to get dressed up and having a themed/costume oriented event will get a lot of people excited as it is an opportunity to express themselves and flex their creative side. We’ve thrown everything from paint parties to 90s après ski themed events, to full moon bashes! 

Whether this is the first corporate retreat your company is ever hosting, or if you are bringing your team back together after some time apart, the above retreat schedule templates can help guide you to a successful team event. Start by deciding whether your event will be meeting or fun focused then following the appropriate best practices to help ensure a smooth event. Ultimately, the length and structure of your corporate retreat will come down to your team’s objectives and ideal budget!