Everything and More That You Need to Know about Company Retreat Planning

While we’re usually busy planning other companies’ retreats, Moniker has been hosting our own internal annual retreat for three years now. Over time, as the team has grown, they’ve become increasingly more complex — yet exponentially more meaningful and necessary as we scale the company.

Here’s how (and why) an actual Corporate Retreat Planning Agency goes about organizing their own retreat. Check out our retreat video of the week before diving into the details!

Why Plan a Retreat?

Every company is going to have their unique reasons both for and against hosting a retreat. There’s a number of factors to take into consideration like size, distribution (where everyone is based), timing, and obviously the finances. The benefits may or may not outweigh the time and resources involved in hosting one, however figuring that out and having clear objectives upfront helps make the decision easier.

In our case, the general purpose of our retreat is two-fold:

1. Business Introspection

Things can get pretty busy throughout the year and travel schedules often overlap. Carving out a moment to step-back as a full group and pry out a magnifying glass to assess the company is paramount to our progress. We focus on evaluating the state of our business (performance), how we do things (processes), and give every member of the team the opportunity to share any ideas they feel would benefit us as a company and culture overall (progress). I can’t stress enough how valuable this can be to getting everyone aligned on the same page and moving forward in the same direction together.

2. Double-Down on Building Culture

As lucky as we are to travel often throughout the year guiding our client’s programs, its rare we get the chance to travel all together and spend time abroad just hanging out without the responsibility of overseeing a client’s program. The retreat offers us the opportunity to learn more about each other outside the office environment, share a few laughs, and enjoy each others company while exploring a new destination. It’s also a chance to sit back and toast ourselves in celebration of the small wins and successes of the past year, which can serve as an important reminder of how far we’ve come and really get people fired up for the road ahead.

Think about what your top 2 or 3 business goals might be, and what tangible results you’d ideally want coming out of a retreat. If your gut feel is that dedicating a time to focusing everyone’s attention on those goals might help achieve them — Do it, and don’t think twice.

In the first few years of the business when we were only 3 or 4 people, the reality was that we couldn’t justify spending the money to throw a proper retreat and doing something half-assed just isn’t in our DNA, so we didn’t do them.

The first edition, January 2018 in Puerto Vallarta, Mexico was actually held at my parent’s vacation home and didn’t involve too much planning or scheduling to be honest. Don’t get me wrong, It wasn’t completely wide open — we had a rough agenda of some topics and issues we wanted to discuss and tackle, but for the most part we carried on as if it was any other week back at our office in Toronto, except with plenty more sunshine in the day (and margaritas in the evenings).

The second edition (January 2019) in Medellin, Colombia involved 6 people and was much different - our first real foray into planning a well thought-out itinerary that clearly felt like something different than a remote working week, similar to what we’ve been helping our clients do for years.

“So how did you do it?”

Great question.

Setting Up a Structure

The most important piece of advice I can offer is to first create a framework and hold everyone accountable to a set schedule, setting aside specific times each day for work, activities, and free time while clearly outlining the agenda people can anticipate.

Share it with the team far in advance, communicating exactly what everyone’s contributions are expected to be and giving them plenty of time to prepare.

Our itinerary from MoniKon 2020 in Morocco. Want to know more? Check out our blog post on Company Retreat Agendas

We’ve established this structure to give everyone the opportunity to touch on their respective team functions as well as any other topic they feel should be shared. It gets everyone presenting in front of the team at least twice, and could easily be adapted to whatever industry you’re in.

1. Business Unit Presentations

Each organizational ‘department’ in our company (e.g. Operations, Trip Planning, Sales & Marketing, Media, etc.) is tasked with joint-presenting a 60 to 90 minute session on a topic directly related to their area of expertise that will help us either make improvements to our current processes, or otherwise re-evaluate whether what we already have in place is still the best approach/system available.

In our most recent retreats, this portion has been responsible for us introducing Asana as our project management tool, rolling out Slack as our core communication platform, and utilizing new software like Brojure to streamline our research & proposal processes. Typically, these are the most impactful sessions we’ll see to our business

2. Individual Workshops

In addition to the above team presentations, we also task each person to choose a topic (literally, it can be anything) they feel would be beneficial for the team to learn about and teach us or lead a workshop on it.

Past examples have included the OCEAN Personality Type evaluations and how to leverage our personality styles to better work together, culture exercises, and a lengthy tutorial on how to leverage our presence on social media into more growth. These sessions tend to be the most eye-opening and interesting from a people point of view.

Our screen got stuck in customs at Casablanca, so we improvised!

In terms of the leadership team and what our contributions are, every year I kick things off with the “State of the Union”my presentation. It’s a very thorough deep dive that’s split into three sections:

  1. The Year Prior (Reflection)
  2. Our Current State, Where We Are Today (Assessment)
  3. The Year Ahead (Roadmap)
Kicking things off with the State of the Union at our Riad in Fez, Morocco

We’re big believers in transparency at Moniker and I truly believe the best way to get people to buy in to the vision and feel a part of it is to be open and honest with everyone— “pulling back the curtains”, so to speak. We go through our wins and losses from the last year, current client roster, a SWOT analysis, and I share and openly discuss financials, income and operating expenses, targets, growth goals, etc. — the whole shebang.

It usually ends up as a 90-minute comprehensive and honest evaluation of how the ship is sailing. I find it really helps galvanize the group into understanding how everyone contributes, where and how the money that comes in gets spent, and how we all fit together as a cohesive team trying to reach our shared goals. This session is usually where I feel most people leave feeling reinvigorated at what we’re building at Moniker as a holistic brand.

That same concept carried on to our third edition, this January in Morocco.

The next section is specifically about the Moroccan retreat itinerary we planned outside the work portion, so if you’re not interested in that, just skip directly to the final Tips & Advice section for help in planning your own retreat

MoniKon 2020 | Morocco

As the company has grown, we’ve chosen to invest in a full week-long retreat that gives us enough time to soak in the experience and get a fair amount of work done, and justify going a bit further abroad as we have in recent years.

We try to choose destinations that are on the cusp of what we think will be “It List” travel spots for the year ahead, and also somewhere we are just curious to explore ourselves. As with Colombia last year, Morocco hit on both of those notes for 2020.

In terms of accommodation, we opted to stay in traditional riads instead of more modern AirBnBs or boutique hotels, and focus exclusively on securing ‘buyouts’ where we would be the only guests on property as it adds a certain dimension of community that you just can’t get staying in larger properties with other people around. Our policy is everyone in their own room, something which I strongly suggest to anyone planning their own retreat. It gives people a private space when they need some time to recharge or just want to step out for a few hours without someone constantly in their space. This is particularly important with companies that have a lot of introverts on their team, who can value personal time as much — if not more than — time with the group.

The MoniKon agenda booklets we made special for the retreat

FEZ | Our First Taste of Morocco

After landing in Casablanca by way of Montreal, we hopped directly into a van and drove 4 hours to Fez, catching a few Z’s along the way. We hired 3rd parties to handle our transportation as it was one less thing to worry about, and quite frankly none of us were too eager to hop behind the wheel in the hectic streets of Morocco.

We chose to spend our first two days in Fez — the historic cultural centre of Morocco — to ease into the schedule and let everyone have a few days to adjust to the time zone and reset before hunkering down to work.

Our first night we stayed in the Riad for a home-cooked traditional dinner and followed up with a game of Telestrations, which is fast becoming a tradition on our retreats. On our first ‘full’ day in Fez, I kicked things off by hosting my annual ‘State of the Union’ address which I touched on above, and we organized a walking tour of the old medina and soukh (market) afterwards to acclimatize ourselves to the ancient city. Our second night dinner was hosted at a local’s home, at the apartment of our driver Ilyaa, whose family joined and cooked us a true Fessi feast.

Left to Right: The view over Fez from the rooftop of our Riad, copper and blacksmiths’ traditional wares, a leather shop in the medina

MARRAKECH | Morocco's Metropolis

After 2 nights in Fez we hopped on a short plane to Marrakech, arguably the most famous city in Morocco and the most likely destination for our clients interested in traveling to the country for their retreats and incentives. We opted against the 5-hour drive and flew to save time wasted in transit, giving us as much time as possible in our destination to explore as well as fit in the work sessions we had planned.

Most of our time in Marrakech was spent in our beautiful home away from home, Riad Darmina, which we found through an online villa rental site. Cost worked out to less per-person than if we stayed in a hotel, and having the place all to ourselves really added a community/family vibe. We look for places that have large common areas, multiple spaces for people to hang out in (together or on their own for a bit), and have one or two sitting areas that would be appropriate for hosting work sessions and presentations.

We also hired a chef to cater breakfast, snacks, and lunch to take one less task off our plates and not have to bother with cooking or the dishes after. It’s also worth double-checking with the hosts what the wifi situation is, asking for them to do a SpeedTest or whether they can boost the speed for a week/month while you visit and offering to cover the cost.

Outside the Riad, we participated in a traditional cooking class at Lotus Chef followed by a walking tour of the old city, mosques, and main soukh. Cooking classes are always a safe bet for a solid ‘teambuilding’ experience without feeling too forced, and it doesn’t matter how experienced a chef everyone is — you get to dive in and do something together while learning about the local culture.

Tagine, anyone?

By day 5 of the retreat, everyone was ready for a chill night in. Unashamedly, by that point we had also our fill of tagine and couscous and opted for getting takeout pizza and a bucket of KFC for a ‘comfort food’ dinner at home. We hosted a movie night with Aladdin (the original!) projected on the wall of our Riad’s courtyard, complete with popcorn. It was awesome :)

Our third day in Marrakech, we spent the morning doing some work sessions before trekking out to the desert to a bedouin camp where we rode camels through the dunes. Steph hosted our final workshop on defining our culture and values, leading us through a madlibs style exercise that led to a few laughs. If you’re looking for an epic backdrop to your next team meeting — hit us up. This was pretty incredible to say the least.

Unique views and venues at the Agafay Desert Tent Camp

We also managed to sneak in one final experience before heading back to Casablanca for a flight home, which certainly crossed off a bucket list item for some, and may have taken the cake for me.

On our final day in Marrakech we got up at the crack of dawn and headed out on a 45-minute drive into the outskirts of the city. We were completely unprepared for how cold the desert is before the sun rises, however it was all worth it once we started heading up in the air in our hot air balloon. As we soared high above the Moroccan countryside, herds of goats and sleepy towns passed by beneath us, while we sailed across the sky led by the wind currents before touching down in a (very angry) farmer’s field.

Firing up before dawn and setting sail over the rural Morocco as the sun breaks through the Atlas Mountain range

CASABLANCA | Final Stop on the Tour

Our final day in Morocco, we hopped aboard a 3-hour train from Marrakech, getting a cabin to ourselves and passing the time playing more Telestrations.

The final stop was Casablanca, made famous by the old Humphrey Bogart classic. We were blown away by how different it was compared to Marrakech, and particularly Fez, where time and the modern world seemed to have not yet intervened as much as we felt when first arriving in Casa. From the art-deco French architecture to the wide boulevards lined with palm trees, it felt more like Nice or Marseilles than the commercial hub of an African nation. We hosted our final evening event — our annual Trivia Night — in the lobby bar of our hotel before heading to a final team dinner at Rick’s Cafe.

Left to Right: French Mediterranean architecture meets Moroccan influence in Casablanca; Team “Neph” having a rough go at Trivia; Rick’s Cafe

We closed out the retreat during dessert, going round the table and asking everyone to share two things:

  1. What their biggest takeaway from the week was
  2. One word to sum up how they were feeling; At the moment, about the future, or whatever that meant to each individual.

In the end, hearing everyone talk about their experiences, what they learnt, and what meant the most to them was pretty impactful. It reinforced why we do this every year and reminded me of just how valuable a proper retreat can be for any company, both large and small, when done right.

Hopefully we've inspired you for your future retreat planning. So let's dive into some of our top tips on how to go about planning your next company retreat.

Tips & Advice: How To Plan Your Own Company Retreat

Having been directly involved in 100+ retreats over the past 7 years, there are plenty of practices and approaches we’ve seen work well and consistently contribute to positive feedback and a better overall experience by attendees. Here are just a few:

Length

There’s equally valid arguments that can be made for shorter vs. longer retreats. You’re essentially taking your entire team offline for a few days, however on the flip side it also takes a few days away before the group dynamics really start to adjust. In our experience, if you can only afford a shorter retreat — time and/or money-wise — try to do a Thursday-Sunday (3 nights) getaway, leaving right after breakfast on Sunday so people still have plenty of time left to spend with family and kids. If you can afford to do longer — Aim for a Monday-Friday, or if further abroad, arriving Sunday night to adjust to the timezone and kick things off on Monday morning fresh.

Location

In terms of destination, there’s a compromise to find between “exotic” and “convenient”. If the group is remote or spread out, finding somewhere accessible in the middle is ideal to save on flight costs as well as time-zone adjustments. Europe is generally a good option, with surprisingly good value once you step outside the main cities or in particularly in Portugal, Spain, and Eastern Europe. On the other hand, if your goal for the retreat is going somewhere truly inspiring you may need to accept traveling a bit further and off the beaten path. Are you in the NY or SF area? Check out other blog posts for great retreat locations in both (Link to SF locationsLink to NY locations).

Rural vs. Urban Setting

In our experience (and particularly for remote team retreats), finding a place 30–90 minutes outside the city is best, ensuring people will stay on property and spend more of their time together instead of heading out on their own exploring. On the flipside, if the retreat is more about work and spending the bulk of your days in meeting rooms, being in the heart of a city allows for people to have quick access to jaunting off on their own or with a few close colleagues during much needed down-time.

Money & Expenses

When possible, try to cover all expenses for employees throughout the retreat. Asking people to go out-of-pocket on transfers, meals, activities, etc. can be a divisive issue that can take away from the spirit of the retreat. Remember, you’re asking people to take a few days away from their families and loved ones and some may see this as a mandatory “work trip” rather than a fun group outing. That being said, in recent years we’ve seen a growing trend towards companies limiting what they will cover, particularly in terms of alcohol (only during dinner, for example) or sometimes not at all. Regardless of your approach, make sure to communicate the expectations around money and expensible items clearly and early to avoid any misunderstandings.

Food & Drink

For larger retreats held in hotels or resorts, this isn’t really an issue as pretty much every meal will be covered/catered. For smaller retreats, our philosophy is hire a chef to take care of breakfast, breaks, and lunch. It means more time to focus on what’s important, and takes away the hassle of grocery shopping, cooking, and cleaning up. Dinners can be a team-led experience, with people volunteering to showcase their inner chef or chipping in with the prep, or heading offsite to a restaurant for dinner. In either case, make sure to pay special attention to people’s specific dietary needs and do all you can to accommodate. Nothing will sour someone’s attitude quicker than being hangry without many options available! Oh, and candy. Can’t forget a well stocked candy or snack basket ;)

Keep to the Schedule

I can’t stress enough how important it is to set a tone right from the beginning about keeping as close to schedule as possible. To make the most use of your time — and to avoid creeping in to people’s down-time — the work sessions need to start and finish on time or be cut and parked for another day. Get comfortable starting a session if not everyone is present. It sends a message that the show begins with or without you, and you’re going to miss out if you’re not there on time. That applies to the leadership team too.

Prepare!

Unfortunately, We’ve seen way more than our fair share of managers and presenters plugging away on their presentations in the lobby or hallways hours before they are meant to lead a large session. A great retreat can be quickly derailed and momentum lost when people start showing up unprepared or half-assing their contributions. It’s not hard to tell when someone hasn’t spent time and put in thoughtful effort to their presentations, and it ends up deflating the energy in the room. Plan well ahead, understand it will take longer than you expect, and be ready days before. You will feel less stressed and people will get more out of it if you show up with a well put together session.

Document Everything

It’s easy to forget while everyone is busy taking in what’s happening on-site or meeting and getting to know their colleagues to stop and appreciate the moment. Consider hiring a photographer or videographer (or delegating that role to someone internally) to capture the highlights and outtakes of the week. A curated album or video that sums up the week shared afterwards really goes a long way towards solidifying the retreat as something truly memorable after the fact.

Ok, maybe a bit too much documenting

Pay Attention to the Little Touches

Branded Swag, custom designed Agendas, Branded Presentation Templates, Welcome Gifts, Daily Notes, etc. — these are all little items that go a long way to creating a more polished impression and overall professional experience. Don’t underestimate the value of the little things that end up in your attendees hands or in front of their eyeballs!

Be Present

Have and enforce a ‘No Phones’ policy during sessions. It shows respect to those presenting but also creates boundaries on ‘work time’ vs. ‘free time’ which lead to more productivity when you need everyone’s undivided attention. That includes the CEO/Founder first and foremost, and sets the tone from the top-down.

Should You Hire Outside Help?

Obviously I’m a bit biased here, but I can tell you from many anecdotes and the feedback we’ve received from CEOs/Founders as well as the HR/Culture teams we’ve worked with; It’s worth it.

Having professional external support is invaluable to allowing the internal team to just focus on content and leave the logistics and planning to the pros. It shifts a tremendous amount of the time and resources involved off their plate and onto people like ours, and you can rest easy knowing the job is going to get done by people who do this for a living. It also allows smaller “People Teams” to quickly scale up the resources allocated towards retreat planning accordian-style without having to add to payroll. Basically, you’re bringing in a team of planning ninjas to get the job done and then get out when it’s over, often for a fraction of the cost of what it would take to hire someone full-time to plan internally, but with access to a full team of professional support.

Some companies aren’t in a position to afford outside help, and that’s totally fine too. Just be mindful about dropping the task on someone within the team who already has a full-time job and plenty of other responsibilities on their plate — it can be overwhelming. If you are planning to do it internally, assign a small committee of 2–3 people to oversee the job and let them divvy up the tasks so nobody finds themselves underwater while trying to balance their regular role with planning the retreat on the side.

Buyout vs. Not? House or Hotel?

In our opinion, having everyone together under one roof is transformative to the general vibe and feel of a company retreat. As companies grow, this gets more and more challenging but as long as it remains an option I would stress to make an effort to find a place where everyone can sleep under the same roof with no other guests on-site at the same time.

When you’re small, AirBnB’s are fine (as well as sites like VRBO, LuxuryRetreats, and similar) but as the number goes up your options get limited to hotels and resorts. When possible, always aim for full buyouts (100% exclusivity). It is infinitely easier for people who may not recognize each other to say ‘hello’ when they know an unfamiliar face is just a colleague they haven’t met yet. This is especially important for remote teams.

What Else To Ensure?

  • Send out a “Save the Date” early on to ensure as many people as possible can participate, and those with kids can plan arrangements accordingly with tons of notice.
  • Respect Personal Space & Privacy during the retreat. Reinforce that “locked doors” means DND, and if you see someone on the phone with a loved one, leave them be unless invited to join the conversation.
  • Set and share a policy towards respecting personal boundaries and behaviour around alcohol. We shouldn’t have to tell you why.
  • Give individuals and teams input on shaping the itinerary and content. A little ownership goes a long way to quality and enthusiasm.
  • Don’t forget to set your Out-of-Office on e-mails and communicate to the outside world where you are and what they can expect in terms of response times for e-mails.
  • Appoint people to be in charge of evening games and icebreakers. Encourage people to bring their favourite boardgames, or other activities people can join in on in a circle and have some fun without drinks being involved.
  • Offer a mix of active and wellness-related activities for those interested. For example, if someone on the team is really in to yoga, see if they would be willing to to lead a class each morning before sessions start. Likewise if there are runners or gym-goers in the group. Too often a busy schedule can overtake people’s normal health routines, but having options built in to the schedule can mitigate that.
  • Mix in ‘all-hands’ team-building with optional activities so people can self-select what they will do based on their own interests. Offer a variety of active/cultural/learning activities to suit all palettes.

Finally — Have fun! Remember, while work is a key part of a retreat, at the end of the day if it’s only about work you could have accomplished it in a drab meeting room elsewhere. Soak up the experience, create shared memories, and make the most of what the destination has to offer! Still looking for more advice? Check out our blog post for '6 Tips for a Successful Retreat!"

Left to Right: The Moniker Crew: Sydney, Steph, Joe, Sean, Tracey, Casey, Ninah