Do's and Don'ts of Company Retreats with Elisa Rueda

Do’s and Don’ts of Company Retreats with Elisa Rueda


Elisa is the founder of The Cowork Experience, a hosting service creating cowork popups socials, retreats, and vacations for clients and their organization or brand. She’s also a contributor at since she now travels back and forth between Bali and the US working with remote and non-remote employees.

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Luis Magalhaes: Welcome ladies and gentlemen to another episode of the Distant Job  podcast, the podcast that’s all about how to build and lead incredible remote teams. I’m your host Luis, and with me today is Elisa Rueda, the founder and the event experience strategy and host of the Cowork Experience helping people have great retreat and the offsite vacations in Bali. She’s a content contributor for, she’s the organizational communications change manager for Capgemini. So welcome to the show Elisa.

Elisa Rueda: Hello, how are you?

Luis Magalhaes: Did I miss anything?

Elisa Rueda: No, I think that’s pretty good, other than I’ve actually left Capgemini. I’m not sure if you got that.

Luis Magalhaes: Okay. Yeah, yeah, yeah. Actually, yeah.

Elisa Rueda: Okay, yeah.

Luis Magalhaes: I wanted the to ask you, I guess that the first thing that comes to my mind is I work and talk to two kinds of companies, companies that have full or partially remote teams, so they have people working outside of their office, and companies that don’t have it but they want to make jump. They want to start expanding their talent pool to include international people, people working from outside the country. So when I was looking at your portfolio and stuff that you did, and especially your organization, The Cowork Experience, a question came to my mind. That question was what makes, for people who are meeting each other for the first time, people who are meeting their team for the first time, what makes a great retreat?

Elisa Rueda: The most pivotal part is the experience aspect of it, right?

Luis Magalhaes: Yeah.

Elisa Rueda: That’s kind of what is the driver of what I do, because it could be from the smallest to the most complicated experience you could possibly have, but if you’re doing it together and you both are going through this experience together, it can have such, such an impact. So your question is how do people, when they first meet, how do they? It’s almost like an icebreaker, but at a very advanced, complex icebreaking way of getting to know people. You know, when I do these cowork experiences, I do it in a remote area of Bali, and people already naturally feel a little vulnerable. They already want to find and seek connection, right? So it puts us in a really positive, an advantage point in that sense. People are ready to connect, and then when they do something that’s interesting and something that’s stimulating together, all it does is it reinforces that connection more. Now, not everyone has the luxury to go to Bali to do something of that sort, but it’s definitely the heart of how we started these experiences, if that makes any sense?

Luis Magalhaes: Yeah. Yeah. So what kinds of experiences have you found that are more bonding to people?

Elisa Rueda: Hmm, I would say three to four different areas. You’ve got health and wellness. People, a lot of times, want to do remote, they want to make these connections because they’ve gone through some emotional life, traumatic experience, and so they want to evolve their lives a little bit deeper and greater. Others do it through productivity. They realize, “You know what? I want to change my life. I want to do something more purposeful,” and so they want to connect with people in a productive environment where they also feel driven to want to do something more for themselves and the world. Then there’s self-development. Now, that’s a little bit more… Health and wellness is more physically inclined. Self-development, I put it more in the kind of a mind and spirit and energy aspect of it, and professional development as well. And so when you’re able to connect with people that want to be challenged, whether it’s because they want to improve their work skills or they want to improve their relationships at home, it really binds people together because they know that they all share similar value sets.

Luis Magalhaes: I see. Who do you think gets the most out of that? Is it regular companies that take everyone off the office and bring them to the retreats for a set period of time? Or do you actually notice that the people that haven’t met the team before get more out of it? How does it feel to you?

Elisa Rueda: It’s both actually. It’s people who’ve known each other and people who don’t know each other. Right? However, the size very much matters, because when you do a retreat our co-work experience retreat, it’s a bit of a more intimate setting and so people are able to have a more deeper connection. They’re able to really kind of explore what the other person is going through. I wouldn’t say professional, but in a very respectable manner. However, I have had clients that have come to me that have 150+ employees, and we just committed to reward our entire company to a trip to Bali and we want to take all of them all at once. That’s something also we can accommodate, and that can also prove valuable too, but then there, their goal is a lot different. When you want to go and take a fairly large group of an organization out together, it’s they want to celebrate, right? They want to celebrate their rewards and their fruits of their labor from a year of sales. While a retreat might be a little bit more focused on development, on growth, and really kind of nurturing some of these skills that they’re trying to blossom.

Luis Magalhaes: All right, so at the moment, or in the past, what kind of interaction have you had with, with remote work? Do you have actually any direct reports? Are you working with someone remotely right now?

Elisa Rueda: Yes. Pretty much the majority of my team is here in Bali. I do have a logistics team here. I also have a team that’s always looking out for content contributors, because what’s so beautiful about Bali is that not only do we get holidayers and tourists, that we also get people that are very, very successful with their content and their business and their services. And so a lot of those content contributors are all centered around self-development, productivity, and health and wellness. And so we have people dedicated to identifying those types of content contributors so when we do match them with our clients, it becomes more of a fit around their content objectives, around the properties they want, around the size of their group. So it’s a two part kind of group that we have, all mainly in Bali.

Luis Magalhaes: Nice. Dealing with people remotely on the client side, what do you usually feel when a company like mine, like Distant Job, that some people, new people haven’t ever met the team so every now and then we try to gather people together so that they can meet each other in person. That’s a nice team-building event for remote only companies. When companies are trying to set up a retreat working with you or with someone else, what are the things that they should be paying attention that they usually don’t? What are the common pitfalls that make things maybe not as good as they could be?

Elisa Rueda: One of the things that I always stress is, as a leader of an organization that’s making these decisions, whether if you’re going to go and do a retreat or not, or a co-ec vacation, or if you’re going to do it, if it’s going to be now, if it’s going to be later, where it’s going to be. The biggest thing is you need to source out. You need to pretty much identify what your problem is and what you’re trying to solve, and that’s usually within the organization. The biggest pitfall is that leaders will make the assumptions that, “Oh, I just need to send them off away and we’ll all have a good time and we’ll come back 100% better. But that’s not always the case.

You want to ask. You want to find out from your organization themselves, they will tell you, “Yes we are struggling with morale,” or “Yes, we’re struggling in having effective team communications across borders,” or “Yes, we’re struggling in how we want to manage our clientele over the wire as well.” So when you see those weak links in your organization, that’s when you want to take the opportunity in a co-work experience retreat or a vacation, because we do still implement content, where we’re able to actually provide more self development around those pitfalls versus assuming your organization just needs a vacation. Does that make sense?

Luis Magalhaes: It makes sense. It makes sense. Though it’s worth pointing out that what people say they want and what people really want or really need is usually quite different.

Elisa Rueda: That is correct.

Luis Magalhaes: How do you coach that conversation? How do you think people should have that conversation and should find out what their team really needs are wants?

Elisa Rueda: Well, so I think the good thing about doing something like this in Bali, the majority are usually really excited about coming to a place like this. No one… Very, very few people are saying no. What’s really critical is when you have these conversations with HR and team leads, you want them to ask their team members, kind of really get into the heart and root in terms of like where we could improve and how you could do it better. That almost sets us up for success, and that’s how I have these conversations is, “We want to win before we play. We want to already know where it is we want to focus or concentrate our time when they are at a retreat or when they are at of vacation.” Let me just explain the differences between having a Cowork Experience retreat and having a Cowork Experience vacation.

Luis Magalhaes: Of course, please do.

Elisa Rueda: A retreat is a little bit more of an intimate setting, between 10 to 20 people. We’re all staying within one property, and it’s a lot more content heavy with bits and pieces of extracurricular activities, cultural explorations, some social, and obviously coworking integrated in this as well. But it’s a lot more intimate. It’s a lot more incubated. However, when you do a co-experience vacation, obviously the driver is festivities, celebration, and that’s fine, but a lot of times, when you go off on these vacations, you can’t completely go offline entirely. That’s where we try to put together an experience that allows you to set aside a cowork space for your employees so that they can come in and out of, throughout the week to work when they have to dedicate hours to the work. We’ll also have health and wellness, but it’s not… The cowork aspect of it is not the driver of the vacation itself. It’s the festivity. It’s the cultural exploration, but we’re able to support the business while you have your employees out on vacation and enjoying Bali and doing their thing, if that makes sense.

Luis Magalhaes: Oh, yeah, yeah. It makes absolutely sense.

Elisa Rueda: Yeah.

Luis Magalhaes: How could a change manager, how does a change manager act when a company has the need to start getting remote people, to start moving, making their operation less office-based and more remote? What are the challenges? How can a change manager help? Because I’ve never had a change manager on the show. So I’m interested, and especially because I think that change management is very important when it comes to remote. I mean, that’s… A big part of my job is evangelizing remote to companies that could really benefit from remote, but for some reason they don’t because they have several fears, you know? But I think that the biggest fear is really fear of change.

Elisa Rueda: When you go into an organization, the one thing you never want to do, and I think most leaders know this is, you never want to go in there and start making rash, aggressive decisions and changes. You know, everything kind of comes with a little bit of a pace, a little bit of time. You want to listen to your organization. You know, you want to take a survey. You might be surprised to learn that more than 50% of your employees don’t want to move out of their office, while maybe 30% of them do. Sometimes they’re motivated by family, kids, or maybe they’re motivated because they don’t. Right? So when you’re trying to evolve your business model from a 100% fully office-based operation to an offsite operation, the key thing is you want to identify who your early adopters would be, and what would they be interested in, versus you assuming that they want to go 100% out because there are people though that, while they love to be remote, they still like to feel like they have some kind of a base.

Luis Magalhaes: Oh yeah, yeah, yeah. I have had people on my team, actually, that told me that, “You know, Louis, I enjoy working at this the job. I enjoy working with you, but I really feel the need to to work in an office with the team really around me.” And you know, that’s fair. Some people enjoy that.

Elisa Rueda: Yeah.

Luis Magalhaes: We don’t need to say that it’s the best way for everyone, but that kind of change comes from two places. It comes from a cost savings place where people realize that an office and co-located people are costly, and it comes from a morale perspective where people think, at least assume, that most of their employees will be happier and more productive working from home. So but as you pointed out, maybe not every employee will be up for that. That’s very common in companies that are growing.

The growth component comes from the talent availability. Regardless of how the people in the office feel, the company needs to hire, and they’re having trouble finding people in their immediate surroundings in a 20 mile radius. Let’s see, so they need to hire internationally. What this means is that, sure the people that want to be at the office and that are already the office can stay in the office, but they will have to adapt to working with people that are not in the office, and leaders will have to adapt to leading teams that are half in the office and half not. How do you advise people process that change?

Elisa Rueda: Well, so once again, the one thing about I’ve learned when it comes to change management is going back to your organization and mining that information. Don’t make these assumptions. You can have some some hypothesis of where you think things should go, but you definitely want to crosscheck by having these internal conversations, having these surveys, really getting a feel for what, and let the data tell you, what kind of organization and what kind of culture do you really have? You may just have half your team that would be interested in and being off base 100% while you have the other half the team that wants just an office, at least a check-in office two days out of the week.

The difference between the generation now of companies and the generation then is, back then it was an all or nothing. It was an absolute kind of decision. If an organization decides on this, all of its employees must follow suit. In today’s generation, the organization needs to listen to their teams, their people, and try to make sure that they can accommodate and meet them halfway in what it is that they want, and remote working is definitely one of those in-demand needs that’s rising in our culture today.

Luis Magalhaes: Hey there, it’s Luis. Welcome to the intermission of The Distant Job podcast. If you are listening to this podcast, there’s a very big chance that you’re interested in building a great remote team. To build a great remote team, you need great remote employees. That’s where Distant Job comes in. Here’s how it works: you tell us the kind of position that you need to fill. We talk to you, we try to figure out not only what are the exact requirements that that person should have, but also we try to figure out who would be a perfect fit for your company culture, because we really believe that that matters. Then once we have an exact picture of what we’re looking for, we’re off to the races. Our recruiters tap into their global network, and we filter people very well so that you don’t waste your time interviewing people that are never going to be of interest to you.

We make sure, because we are techies and our recruiters are techies, as well, so when people get to you they are already pre-selected and you just have to decide between the cream of the crop. And once you make your selection, we handle all the paperwork, we handle HR for you, we handle payments, and you get a full time remote employee that’s among the best on the world and managed entirely by you, by your processes and following your culture. If this sounds good, visit us at And without further ado, let’s get back with the show. Thank you for listening.

So, let’s say that you were working on a team for your company. You suddenly needed to hire a team that was not in Bali. For some reason, you couldn’t find in Bali the people you needed, and they weren’t willing to relocate. What change would that mean for your way of management, for your management style? How would you work things out?

Elisa Rueda: The way you want to work things out when you begin working with a team that’s remote from you is, you first need to identify your preferred and most effective work styles. And your time. Time zone is really, really critical in terms of what are your peak performance times throughout the day and when can you incubate certain activities like calls, certain activities in terms of when you guys have team meetings internally, and then as you start branching out and growing your team internationally, you start to set those expectations of a thing. Look, we absolutely don’t mind you being remote, but just as long as you’re able to meet these expectations for us to meet our peak performance, then we should be fine. But you need to know that for yourself first before you can go out and start assuming people will just know how you’ll work.

Luis Magalhaes: Yeah. Yeah, it does. It does. It does make sense. Okay. So on a more personal note, we were talking before we started recording how you currently split your work life between the US and Bali. You go back and forth, right? Tell me a story of a lesson that you learned doing that. You know, going back and forth, what was your biggest insight and how did it come about? Because I assume that’s when you go to the US, you don’t drag your team with you. Right?

Elisa Rueda: No, I don’t.

Luis Magalhaes: So, what’s the biggest insight, the biggest lesson that you went for there? Was there any event, any story that you can tell that’s really crystallized it for you?

Elisa Rueda: Well, so there is. You know, one of the biggest insights I had, actually it was really interesting, is the cultural difference in communication, and I think that that is probably a very universal heartache sometimes, because I remember the team when we first started, and we needed to scout out some properties for a client and I was in the us and my team was in Bali. At the time, they were not accustomed to… They felt like they could only respond if they had the perfect or the right answer for me.

It was the one little detail, but then after speaking to them, after coaching through them, I said, “No, what it is is we’re building trust. We need to make sure that you’re transparent in what you’re doing, you are transparent what I’m doing so that we’re able to build this team together and we’re able to build a results. If you are absolutely swamped with other priorities that I’ve provided for you, that’s absolutely fine. We just need to talk this out because that’s all we have when you guys are to in two different countries.”

And so that very insightful for me is really, really identifying, “Okay, what’s your communication style? Is this person comfortable knowing that they can call me when there’s a problem? Does this person know that it’s better to be transparent about what they’re doing versus not telling me anything because they don’t have the right answer?

Luis Magalhaes: Got it. Got it. Okay. Let’s say that I’m planning a retreat for my team.

Elisa Rueda: Okay.

Luis Magalhaes: Apart from just polling them and knowing how they feel about it and what they want to do, give me three actionable things that I can do to make sure that it’s smooth sailing. It is really building trust, as you said, because that’s what people need mostly when they are working remotely. The reason we get people together is mainly to build trust and to humanize people. Right?

Elisa Rueda: Correct.

Luis Magalhaes: So that people understand that it’s not just a voice in the other side of the computer that they’re dealing with it. It’s a real human being.

Elisa Rueda: Correct. Correct. One of the things that… Three action items I would give you as a team lead over your organization that’s going to join us for a retreat is, one identify. There’s two types of areas that you want to identify from your team members. One, how would you like to improve professionally, whether it’s within your individual contributing space or whether it’s at a team capacity. Tell me how you want to develop professionally, one, and then two, the same question but at the personal level. Is it that you want to work out more? Is it that you want to eat better? Is it that that you feel that you want to have better exercise routine? Now, while those questions seem really easy to ask and easy to answer, it actually gives you a lot more insight in terms of what they feel is not their strength, which is what their weakness may be.

Luis Magalhaes: Ah, yes.

Elisa Rueda: And so that’s very telling. And then as far as your third action would be more so to understand, “Okay, so if we did this, what relationships would you like to blossom? What relationships would you like to grow more trust in?” Because then you’re giving them the opportunity to really kind of network. They not only see a value in strengthening their relationships with their current team members, but they also see the opportunity of building new ones outside of that.

Luis Magalhaes: Oh, okay awesome. Thank you. That sounds useful. Okay. Moving on to to a different, more relaxed question. What purchase has made your work life easier or more productive in the past year?

Elisa Rueda: Oh my gosh. I’ve got a lot. There’s a bit. There’s a few things, right? There’s things from… You know, people really undermine the value of ergonomics. I feel like one of the benefits of working in an office, especially when I was in the oil and gas industry as a change manager back in Houston and in Austin, is they’ve put a lot of value in ergonomics, how to set it up right, how to make sure that you’re looking correctly at your laptop and how your body’s positioned. But then once you start to work remotely, no one’s really paying attention to that. And then all of a sudden you start to feel a little crack in your neck. You know, you start to feel a little sore and you don’t know what that is, and no one is around to tell you that “You know what? You might not be sitting right. You may be twisting your neck incorrectly and it’s going to have longterm damage.”

And so, even though I’m here in Bali, I still travel with my neck stand, with my portable keyboard, with my proper mouse, because I know at the end of the day, this is super critical that I’m actually sitting upright as I’m working long hours here in front of my laptop working remotely. Now, I know that doesn’t sound like a big purchase, but it is. It has a huge, huge repercussions if you don’t invest correctly in that area.

Luis Magalhaes: Nice. I should look into a nice chair for me.

Elisa Rueda: Yeah, yeah.

Luis Magalhaes: I still use a kitchen chair or something like that. Okay, so what about books? What books have you gifted the most? What books have influenced you more in the way you conduct your business and your work life?

Elisa Rueda: Man, there’s a few, actually.

Luis Magalhaes: Okay. I was going to say if you’re not a book person, you can point me to lessons or podcasts or stuff like that. But books are great.

Elisa Rueda: Yeah, podcasts, it’s The School of Greatness is one that I definitely refer to quite a bit. Gary V’s podcast I’m listening to quite a bit. I really enjoy that. I would have to say I’m more of a podcast kind of person than books these days. Yeah, I think that’s kind of what… Oh man, you got me on that one because I have think about this for a second.

Luis Magalhaes: Okay.

Elisa Rueda: But the one I definitely want to read up is Win Before You Play. There’s a book about that, and that’s something I feel that’s very much in alignment with how I pursue my work.

Luis Magalhaes: Okay, sounds cool. Final question. If you could have the attention of the tech industry for one minute, what message would you give? What message would you make across about leadership, about management, about remote work? If you feel like it.

Elisa Rueda: Change. Change, change, change. Always know one thing. The extremity of anything is harmful, right? You’re in an office 24/7, you know five days out of the week. That’s not fun. You work remotely 100% of the time, and you’re incubated, isolated that’s not fun either. Having a balance is key, and I feel like we’re evolving to that. Right now, the pendulum was far to the left with being in office, and now it’s starting to go far to the right with remote. But at some point, the pendulum has to come down in the middle where we get a little bit of access to both. I feel like right now, if an organization wants to get ahead of that, it’s about listening to your organization, to your teams, but also understanding what’s an ideal balance between the two.

Luis Magalhaes: Sounds great. Sounds like a good message. Thank you so much Elisa. It was a pleasure having you. It was a pleasure talking to you. Tell me where people can find you online. Where can they continue the conversation with you? Where can they find more about your company and the services it provides?

Elisa Rueda: Yeah, no problem. I am… Pretty much my work is at, and a lot of my work right now is currently based in Bali and in the US. We are looking to move into South America where we would service clients there as well too, since it’s a current time zone. But you come to my site and this is where we kind of open up the conversation in terms of what kind of experience you want for your teams and your organizations, because these days no one wants to get stuck in a hotel box for a Christmas party. You know, going off site for a cowork experience experiences now the new thing. And that’s what we do.

Luis Magalhaes: Nice. Nice. Okay, so that sounds great. I hope people get in touch, and yeah, thank you so much. It was a pleasure talking.

Elisa Rueda: Yeah. And by the way, you can contact me at [email protected], and I’ll be there and available anytime.

Luis Magalhaes: Wonderful. See you around, then.

Elisa Rueda: Thank you.

Luis Magalhaes: And so we close another episode of the Distant Job podcast. If you enjoyed the episode, please, you can help us out by sharing it on social media. That would be great. It’s how we reach more listeners, and the more listeners we have, the more awesome guests I can get in touch and convince to participate in these conversations that are a joy to have for me, and I hope they’re a joy for you to listen to as well. You can also help a lot leaving reviews on iTunes or your podcast syndication service of choice. Reviews are surprisingly helpful in helping the podcast get to more listeners. Now, another thing that you might want to do is go to, click on your favorite episode, any episode really, and subscribe. By subscribing, you will get a notification whenever a new episode is up and whenever we get the transcripts of the episodes up so you can peruse the conversations in text form.

And of course, if you need to find a great employee for your team, a great remote employee, you should take the whole world into consideration and not just look to hire locally, not just look to hire in your country. Look around the whole world, because that’s the talent pool that contains the best talent. And to help you with that, again, is the perfect place to start. You will tell us who we need and we will make sure that you get the best possible candidate 40% faster than the industry standard. And with that, I bid you adieu. See you next week on the next episode.

For further inquiries regarding podcasts, eBooks, blog posts, or general information about remote recruitment don’t hesitate to send us an email at [email protected]  

There’s a difference between a cowork experience retreat and a cowork experience vacation. When you take a large group out the goal is to celebrate, but a retreat is more focused on development, growth, and nurturing the skills of the team members. 

Before going on a retreat, Elisa shares it’s important to identify the problem you’re looking to solve so your time is focused on finding a solution to that specific problem. Don’t just send your employees away to have a good time as you’ll probably come back the same way.

What makes a good company retreat? How do people break the ice when they meet and get to know each other for the first time? Listen to this podcast episode and find out.


Elisa’s favorite podcasts:


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