Dear Monsters,

Leading in the world of remote work isn’t an easy task. With teams spanning different cities, countries, or even continents, in-person events and retreats are making a comeback in full glory. These events present a unique opportunity to energize people toward a common goal, inspire them, and help them get to know each other better. Retreats transform people into better versions of themselves in a way that feels natural, safe, and inspiring.

But there’s always a downside… Aren’t you tired of attending offsite events that leave you feeling drained rather than inspired? I know I have been. And although I always find a way to make the most of an offsite event or retreat, I have been disappointed or even angry, as I did not get as much value from them as expected. New Age Leaders are facing many challenges, and leading offsite events and retreats is just one of those tasks that they never teach you in school.

It sounds harsh, I know, but there is hope and there is a solution. After years of trial and error, I’ve cracked the code on how to turn these events from dull affairs into dynamic experiences that leave everyone buzzing with excitement.

Having organized over a dozen offsite events for my own teams, spanning across generations, countries, and even continents, I’ve encountered my fair share of pitfalls and triumphs. From navigating diverse perspectives to keeping everyone engaged, I’ve learned invaluable lessons along the way that have transformed ordinary gatherings into unforgettable adventures.

So, if you’re ready to ditch the boredom and reignite the spark in your team, join me on a journey as I share the insights and strategies I’ve gained through firsthand experience. Let’s dive into the art of designing offsite events that not only meet expectations but exceed them, leaving participants energized, inspired, and ready to conquer new challenges.

1. Break the Ice: Getting people together is not about numbers or strategy. It is about connection. An offsite event helps you to create team feeling. Use the opportunity to help the participants get to know each other at a deeper level. At my last event, everybody was asked to provide a fun fact about themselves and then drew it out of a hat. We facilitated a “speed dating” session where everybody had to look for their person without using the words on the card. We spent over an hour on this exercise, which might look like a lot, but boy did it help to get the creative juices running and to break down barriers between the team.
2. Break Down the Sessions: There’s always lots of content to share, and you might fall into the trap of oversharing. Packing the agenda with too much content and sessions that are too long and leave no space for dialogue can be a real downer. I always put myself in my team’s shoes – I wouldn’t want to sit and listen to presentations all day long. People want to stretch their legs, engage in some one-on-one chats, have a coffee, or conduct business or private calls, so it serves no purpose to restrain them. Putting in enough breaks and fun activities that get people moving at the right time in the day makes all the difference. I like to include breakout sessions and workshops that allow people to go outside and find their creative oasis while getting some time in the sun and fresh air.
3. Get Everybody to Contribute: For smaller events that are under 30 people, I am a firm believer everybody should get their time on stage, even if it is only for 5 minutes. Be inclusive to everybody on the team, regardless of age or seniority, and give them the possibility to publicly contribute. This strategy works wonders to help team members feel like they truly matter and are needed during the retreat. In this way, you also prevent them from disengaging and spending all day on their phones.
4. Use Randomizers: The randomized wheel can be your best friend. To ensure that everybody doesn’t do their part and check out, include a randomized selection of presenters or challengers. My secret is to always keep the element of surprise and to let it work to my advantage. Of course, people should know what to expect, so I would not keep an outdoor activity that requires a special kind of footwear as a secret, but still, I try to ensure there is some level of suspense during the event. Teams stay alert in this way and continuously engage and listen because nobody wants to be put on the spot and not know what to say, right?
5. Practice New Concepts: Offsites and retreats are usually about getting people outside their comfort zone and wiring them to do something completely new. We usually discuss new products and propositions or new leadership practices. I like to include a playful element, making people build something with their hands, get up on their feet or even role-play. My guiding principle is: if it can be done on Zoom, it shouldn’t be part of the retreat. Try to use most of the sessions to break traditional patterns and ways of thinking. It is key to design the workshops to still be practical and useful for participants once they come back to their real-life environment.
6. Don’t Stick to Timings: As always, every agenda is packed. Although I am usually very strict and disciplined in a traditional environment, I would not let a presenter go on for longer than planned, but I would also never want to interrupt a good discussion during a retreat. As a leader, you need to be flexible and stay prepared to let some sessions go or shorten them to accommodate a deep exchange between the participants. Again, these are the parts that usually don’t happen in a traditional setting, so if you do encounter some fruitful friction or challenging questions, make sure you spend enough time on them.
7. Challenge: Sometimes it’s totally okay to be provocative and bring up new concepts or call out what needs to improve. Doing all the steps above will create a safe space for team members to feel safe and take feedback. In this case, it is important to understand that not everybody will feel comfortable stepping outside their comfort zone, regardless of the shoes they are wearing! The key for retreat leaders is to make people comfortable in their discomfort because that is exactly where growth happens.
8. Integrate: True retreats offer the flexibility to integrate the leadership or business practices with action-driven or spiritual practices. I like to connect these concepts to demonstrate the true power of adopting a new behavior. Adding physical movement, such as yoga, running, or swimming to the agenda might sound unorthodox, but it can work wonders, especially when you reframe them in a way that re-emphasizes the message of our retreat.
9. Include External Voices: Offsite events and retreats present a unique opportunity to invite keynote speakers, coaches, trainers, clients, or other interesting personalities to run a workshop that will provide the event with a special flavor. Whether you like it or not, people usually seem to value external voices much more than internal ones, especially if they are delivered in a professional way. This item does come with a cost, but it is always worth the money.
10. Collaborate: Last but not least – don’t do it alone. You need a good organizational team that will show diverse perspectives and help you create the entire experience. The result is energy, engagement, honesty, and yes… laughter!

Dear Monsters, now you have the 10 key principles on how to organize effective offsite events, based on my extensive experience organizing such retreats for diverse audiences. If you are a fan of attending such events, I have designed a transformative experience for New Age Leaders and Entrepreneurs in October 2024 (17th to 20th) for a small group of established female leaders on the wonderful island of Mallorca. You can use this link to learn more and apply.

Until next time,

Helena Zikova

Photo by Antenna on Unsplash