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

While we’re usually busy planning other companies’ retreats, Moniker has been hosting our own internal annual retreat for six 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 a guide to planning a company retreat, as told by an actual corporate retreat planners.

Why Plan a Company Retreat?

Every company is going to have their unique reasons both for and against hosting a corporate retreat. There’s a number of factors to take into consideration like size, distribution (where everyone is based), timing, and obviously the finances (here’s a link on how much a company retreat really costs). 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 company 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.

“So ... how do you plan a company retreat?”

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.

Company Retreat Agenda Example

Our itinerary from our 2020 retreat 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.

Full-team workshops at our company retreat in Morocco

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

In terms of the leadership team and what our contributions are, every year we kick things off with the “State of the Union”. 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)

It usually ends up as a 90-minute comprehensive and honest evaluation of how the ship is sailing. This 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 where most people leave the retreat feeling reinvigorated.

State of the Union Presentation at the company retreat

Tips & Advice For Planning A Company Retreat

Having been directly involved in 200+ retreats over the past 10 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:

Retreat Schedule and 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. Here are a couple of retreat schedule templates for whatever length of time is best for your team. 


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. Need some inspiration? Check out other blog posts for great retreat locations in California, Colorado, Texas, London, Mexico, Lisbon and The UK

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 corporate 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 company 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 company 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.

Make Team-building fun!

The words team-building can be completely cringe-worthy. Since Company retreats are meant to help your team get inspired, it’s time to really shake things up if you want to see results. We’ve put together company retreat tream-building ideas that have always been a hit at the retreats we’ve planned, and are actually fun. Always ensure you’re planning activities that are inclusive of everyone’s activity levels and it’s a bonus if you can incorporate the local culture!

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.

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.
  • 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 team retreat planning resources and our blog post for '6 Tips for a Successful Retreat!"

The Moniker crew at their company retreat in Morocco