This week we are talking about company retreats with Elisa Rueda, founder at Cowork Experience.

Following the last interview with Vivian Acquah talking about wellbeing at work, we sat down with Elisa to talk about how companies can benefit from taking some time to change environment and de-stress or focus on specific initiatives.

Elisa decided to combine her change management experience, understanding of business needs and the passion for events, to design a suite of experiences and services to support companies.

With Elisa we touched on why company retreats are gaining in popularity and what are the related benefits, what are the elements to consider to create a quality experience for a diverse group of people and how to do planning the right way.

I thank Elisa for taking the time to her her knowledge and experience, and I hope you'll find this interesting.



Elisa, could you tell us a bit about your background?

For most of my corporate career, I was an organizational change manager where I managed the people side of internal changes for large corporate clients. I led business units and groups through such transitions by building out strategic adoption plans and content to facilitate that. My work spanned from corporate communications, leader town halls, training plans to team building workshops.

When I left and started traveling, I revisited my natural passion for events in these remote (expat-heavy, digital nomad centric) markets. I quickly grew a network and expertise in creating market-activation events to help promote client brands in foreign ground. Ultimately, my background with people, communication, event experiences and content, plus my deep global network, eventually brought me here to service clients with global retreats, annuals and remote market cowork events. What started out as co-work popups quickly turned into a suite of experience options and services.

Is it coincidental? I don’t know. This work inherently prepared me for what I would do today with the Cowork Experience (CoEX) where my work is centered around a co-work experience.

Team building off-sites and company retreats are gaining in popularity. These represent opportunities for the employees to de-stress but also to bond with each other and ultimately work better/generate better business results. In your experience, what are the key outcomes of a successful initiative of this kind?

It depends a lot on the client’s experience objectives. If it’s a project-based or a productive-heavy trip, usually, some of the key outcomes are meeting project completion goals, improved workflow, increased communication, learning member strengths, and familiarity with the team’s ebbs and flows.

If it’s more leisure-centric where it’s part activity and part co-work, those key
outcomes are around team members’ interpersonal awareness such as increased understanding of each other’s work role, their strengths, commonalities, personal projects, and self-improvement goals.

Especially for remote and distributed teams, a company event is the perfect moment to bring people together, and often for people to meet for the first time. How do you facilitate connections and a sense of belonging for all those involved?

Not everyone is an extrovert to ask questions and we can’t assume that everyone knows the right questions to ask. So, we start by bookending the retreats with team interpersonal assessments to gauge and challenge them on what they know about each other. Here they begin to realize some commonalities and interesting things. Throughout the week, they progressively learn more and here is how:

We’ll weave the team’s passions and projects into the retreat's content program through activities, talks or highlights. The goal is to curate an experience that’s relevant and meaningful. It does wonders when everyone feels represented somewhere in the experience. This allows opportunity for the group to “spot and bridge” connections around topics they’re openly comfortable with, all while the team gets to explore new things.

Inclusivity is another important aspect to consider when you have your entire company together in an informal setting. How do you create an environment able to embrace and celebrate diversity?

This is where we pride ourselves in weaving in team member interests, passions, and projects into the program content. Depending on the subject, sensitivity-level and team insight, we’ll explore how we can bring focus to a topic and promote positive change or awareness.

Having a large group of people traveling abroad and spending a good portion of time together outside the “safe” traditional work environment can present some challenges. How can you mitigate potential risks?

No one wants an accident nor an offensive misunderstanding. It can affect a team's experience greatly. To avoid high risk scenarios, firstly, we’d advise that the itinerary is revised so that there are no surprises and all the activities are vetted and approved.

In addition, we advise to maintain a respectful attitude and safe behavior as teams would in their usual working environment and as a guest in someone else’s country. We recommend to cross-check safety needs and requirements. Some items include travel medical insurance, waivers, liabilities, and business continuity planning. Especially with team annuals where the whole company lot comes together, its standard procedure for many companies to ensure not all members travel on the same flight.

Last, we'd encourage teams to identify and share their emergency contact within the team.

For companies looking to organise their very first company retreat, what would your top suggestions be? And what are the things to consider to ensure correct planning and smooth operations?

Great question! I’d suggest companies start piecing together all the details they need sooner rather than later. Here is a basic run down to get you started.

Plan with time. We recommend at least 2 months to develop their retreat. For annuals, due to scale, we suggest January or the first quarter of every year to begin planning. There are a number of moving parts that have to come together to finalize an end-to-end trip with that many people. One detail many learn later is they have to reserve whole resorts or properties which are not readily available. Sometimes we have to consider an alternative accommodation strategy which can take weeks if all the parties come together. Another detail is setting up co-working memberships and team rooms. They book up fast and early especially by local teams.

Not to mention, planning with time allows the opportunity to get ahead of peak season rate increases including flights.

Confirm your location early on. Location should be leadership’s first and foremost settled decision by the beginning of the year. Many hold back because they are worried that the location may be restrictive or out of budget. Our approach is to make the location work within the company's guidelines and requirements. To add, annuals are annual. Create a 5 year location plan so that everyone knows their destination preference is on the list. This alleviates the pressure to making a destination decision that year. It’s fair to expect that the team will make it to all the suggested places eventually.

Then there are a series of other data points like the work schedule, accommodation preferences, meal planning, etc. Since we know the questions to ask and how specific the answers need to be, we’ve helped clients streamline their team retreat requests too when they have multiple teams meeting throughout the year. We assist team leads to vet their requests and confirm their decisions. By the time the operations or people team get their retreat request, they have all the information to approve and signal to the team and us to move ahead.

Prepare your team for flight purchases early on. I'd advise to have teams prepared with a flight expense plan and enabled for price watch deals early which can be during the planning.  More specifically, when we place the accommodation deposit which can be 6 months before. The team will find great savings throughout that time. This gets the team ready to snatch bargains when they can.

As for how to ensure correct planning and smooth operations, we have checkpoints built in our development process. This helps everyone stay on the same page, share any course corrections, and ultimately ensure that the final product is fit for them.

What are some of the best or most popular locations that can make a team-building experience truly special?

It depends on their experience objectives! But one insight I suggest is to target markets with a heavy digital nomad culture as wifi, infrastructure, and low cost have been likely vetted.

If it’s project-focused where they’re incubating themselves for long periods, like a hackathon (projectathon) trip, I recommend a vibrant metro place like Lisbon, Portugal or Chiang Mai, Thailand. You’ll want to be sure to place your team members in a location where they have the freedom and access to break away in their limited windows with plenty of things to do on their own or with others versus a remote location where you’re stuck!

However, more importantly, since their priority is technically a “lock-in”, we optimize their experience within their team room. The goal is to revive energy, pump the creative juices and maintain a healthy workflow heartbeat. We incorporate a variety of in-room and out of the room activities for breaks as well as culinary tastings.

Lastly, to add to the projectathon experience, I’d work with the team lead to see if there may be an opportunity to vet the team’s developments with a local focus group, sometimes with a final presentation if that serves an incentive and for quality assurance.

If their objectives are more centered around building the soft side of the team, like trust and relationship, I recommend Canary Islands, Spain or Bali, Indonesia. Here we'd place them in a remote retreat space where they can dedicate their days between working, personal, and interpersonal development. We'd create a dynamic schedule of activities, talks and workouts to name a few, complemented with some off-sites.

Finally, with a heavy team presence in one location, it can be a great chance to promote, recruit or educate on any new programs, products, or services. We'd check to see if there is an opportunity for company growth. This is also a great team project to add to the retreat. Having hosted many events globally, I have the network and experience to leverage from. It’s another great benefit for clients to tack on to their team trip. I’m a firm believer in providing multiple value points in our experiences.

Where can people connect or find out more about you?

You can reach me via email at elisa@thecoworkexperience.com.


If you have experience revolving around startups, people and culture, ping us on Twitter @HumaansHQ or drop me an email at giovanni@humaans.io. We'd love to learn from your journey and share your learnings.


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