How We Organized a Remarkable Offsite: 10 Learnings to Take into Account


For the first time, we organized our company offsite. Eighteen colleagues joined from 12 different countries, of which some had never left their home country.

After a poorly planned and organized workation in 2019, we learned our lessons and created a memorable offsite in Lisbon, Portugal. We share our main learnings below.

Before we start: Dive into Matchr’s offsite atmosphere 

Now, when you are energized and inspired, let’s move on with the key learnings to help you organize amazing offsite. 

Organizing Offsite: 10 Learnings

#1: Book everything in advance

We planned our offsite 6 months in advance. It turned out we should have planned our dates even earlier. We underestimated how long some visa processes were. Some of our colleagues from Nigeria and India couldn’t join because the visa process took too long.

The next point is that booking in advance means lower overall costs. Make sure that tickets and accommodation are booked at least 6 months in advance. You can easily save up to 20-30%.

#2: Communicate upfront

Be clear about what your employees can expect and what the day-by-day agenda looks like. Try to communicate this as early as possible so people can (mentally) prepare. For some people, traveling across the world to a foreign country and spending several days with colleagues that you have never met can be stressful. By communicating upfront to our colleagues what to expect, what to bring, and where they would be staying, we could mitigate this.

As a positive side effect, it helps build the excitement of (finally) meeting each other in person.

Instead of writing long-read emails and many times explaining the same points, we created a handbook that covered all the most important things. 

Pro tip: When you create documents for internal communications, make sure they are designed well and attractive. Such attention to detail shows that you care about your employees, who are as important to you as your clients or other stakeholders. 

#3: Keep the work and fun balance

In contrary to our workation, we managed our work-relax balance well. Out of the 3 full days together, we had one training / working day and two fun days. 

Be clear about what your intention is for your offsite. Is it to discuss strategy or grow deeper connections with one another? For us, it was clearly the latter, so we made sure that the focus was on social activities vs. work-related activities.

#4: Assign someone to organize the event

Make sure to assign someone to the offside that is strong from an operational perspective and detail-oriented. In our case, our Head of Events, Victor Zhuk planned and organized everything. Victor spent hours finding the right restaurants, hotels, and activities and created a buzz for the offsite in the weeks leading up to the offsite.

Adriaan Kolff (on the right); Victor Zhuk (on the left)

Don’t make the mistake of assigning a colleague that needs to organize the offsite next to his/her regular job. You risk spending a lot of money bringing everyone together to show up at a restaurant where they have never heard of you.

#5: Plan your training day

We had one day dedicated to training and workshops. We underestimated how valuable it is to have everyone in the same room and do a workshop together. We analyzed upfront where the biggest need in terms of training was for our employees. This made this day very productive even though some colleagues would have liked two training mornings vs. one long day.

As not everyone in our company could join, we made sure that we had a professional setup with different cameras, sound, and headsets for the presenters. This made it for our colleagues that dialed in remotely a pleasant experience to join.

#6: Nurture connection

Focus on creating a deeper connection with your colleagues. You can do this through shared experiences and workshops. We asked our colleagues to discuss several personal topics over dinner and lunch. This worked well for us. 

We split the group into teams of 6 and asked them to discuss one thing they all had in common. For example, they all had a university degree or climbed a mountain. And secondly, one thing that made the unique in the group of six. For example, someone used to swim professionally, someone could write with both hands, and one person got arrested.

On our second night, we split the group into teams of 4 and 5 and asked everyone to share two challenges they overcame in their life. This exercise turned out to be very powerful as colleagues shared their life stories very openly and vulnerably.

These activities created a deeper connection and bonding between our colleagues.

#7: Create magic

Make sure to create several moments of magic during the offsite. 

Some of our magic moments:

  • A personal welcome card fully branded in our company’s colors on everyone’s pillow when they check-in.
  • We organized a tour on two very fast speedboats to explore Lisbon by water
  • We had dinner on a rooftop overlooking Lisbon
  • We had lunch on the beach next to the ocean
  • A themed dinner in which everyone was asked to bring a gift from their home country and dress up in traditional clothes.

What we should have done was to give out company swag for our employees to wear. At the time of our offsite we were in the midst of our rebranding and didn’t want to spend the money on t-shirts with the old logo and style.

#8: Involve everyone

Try to involve your colleagues by asking them to organize a fun activity or have them involved in the workshops. 

We asked everyone to bring a gift from their home country, to dress in their national colors, and to tell in small groups what one thing they were proud of and one stereotype of their country. Some colleagues put a lot of effort into presenting their country and brought amazing gifts for other colleagues.

#9: Integrate folks who couldn’t join

Make sure you integrate the rest of the team that couldn’t join when you get back. Truly take time to share the stories, learnings, and insight jokes of the offside.

For next year will send the entire agenda earlier to our team that can’t join in person and try to create more moments during the event itself to engage them with what we are doing.

#10: Collect feedback

Send a survey to ask for detailed feedback on your offsite to make sure you can improve for the next event.

All of our employees rated our offsite with a 5 out of 5. Our main point of feedback was:

  • To communicate upfront that colleagues would be sharing rooms.
  • To split the training day into two parts across two days.
  • To have a bit more variety in terms of the food offered by the hotel (they only served fish)
  • That the next offsite should be longer.

Wrapping up: The offsite success checklist

Without further ado, here is what you can do to make your offsite a success:

  • Prepare everything in advance to make sure everyone will be on board and you won’t run over your budget.
  • Avoid hectic communications and clearly deliver the offsite goals, expectations, agenda, etc.
  • Keep the work and fun balance to avoid your offsite being too boring or, on the contrary, just a lovely trip. 
  • Make sure there is a dedicated person in your company who will be in charge of the whole event. 
  • Plan your training days to improve your team’s skillsets.
  • Organize activities to create a deeper connection and bonding between colleagues.
  • Involve everyone, even folks who can’t join the offsite in person.
  • And don’t forget about magic. 

Follow these simple steps, and your offsite should be a success!

We are constantly searching for talented and experienced recruiters. Check the current openings and apply to join us. Maybe, you will be with us during the next offsite. Who knows 🙂

Article by:
CEO and Co-founder of Matchr
CEO and Co-founder of Matchr
mail icon
Subscribe to our monthly updates
We have more articles you'd love