An over-planned agenda, running out of drinks, and hidden costs. As the Chief of Staff at TradeLink, I have organized the occasional offsite events for our employees. And surprisingly, not everything has always gone smoothly. With this article, I am sharing our learnings of the planning and execution of three international company offsites within the last 18 months. This article will help you avoid some initial mistakes and give a supporting perspective to succeed with your next offsite planning.

Before jumping into the topic, I will give you some background on our company history, the purpose of our offsites, and how we believe that that help to energize our remote culture.

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A brief history of TradeLink

Our founding hour precedes the beginning of the Covid pandemic in Europe in early February 2020. After the first few months in the hybrid setup, we went all-in to build a fully remote-first company in October 2020. The opportunities we identified outweighed all of our concerns, and we proactively engaged in building a remote-first culture following the frontrunners Gitlab, Basecamp, or Buffer.

Today, our team marks a talent tree from 3 continents, 9 countries, and 14 nationalities. In total, we are 65 people connected across more than 30 cities within Europe, Asia, and Africa.

While we are learning more and more about creating a more compelling, socially engaging, and enjoyable remote work environment (this deserves its own article), the urge to spend time together on-site and celebrate joint successes is unabated. Hence, company retreats have been a fundamental pillar of our culture. They serve as a secret ingredient for a boiler room experience. We nurture this tradition by coming physically together every six months. Thus, for us, offsites are rather onsites.

In total, we have had 4 onsites since the summer of 2020, whereby this article refers to the last three with a significant organizational effort (the first was more a meeting in a conference room 😄). In September 2021, our team of 25 people met in Tuscany, Italy, for 4 days. In May 2022, we repeated this endeavor in a new location for the 50 team members. Finally, we closed the year 2022 with the second onsite. The team met near Leipzig, Germany, at the beginning of December.

It sounds rosy, but you, in the driving seat, also know that much work and decision-making goes into it. Behind the onsite magic, there are multiple personal preferences, team and leadership demands, budget limits, and legal frameworks. However in the end, everyone wants to have the best time of the year together. So from that, we have gone through many team sessions, read dozens of blog articles, talked to peers, and experimented a lot.

The following chapter summarises some of our operational pillars central to our onsites success.

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Organization pillars and our perspective

1) Finding an appropriate location

With a company onsite, we are not just gathering at a particular place. You instead create a common denominator, a shared experience, a joint moment that everyone remembers fondly. Thus, the location sets the anchor. But what makes a great location?

• A) Isolation — For a connected and remarkable experience, you want to be alone within your team. You want the feeling of being sworn in and the freedom of movement the entire time. This decision dissolves dependencies from the beginning; hence, renting a location alone is a must-have criterion for us.
• B) Adequate standard — The promise of a shared onsite is that your teammates will perceive it as a reward, appreciation for their hard work, and an opportunity to recharge their batteries. We consider it essential to provide an appropriate standard for the entire stay. This ranges across all factors, i.e., equipment, cleanness, and atmosphere.
• C) Infrastructure connections — This point is self-explanatory. As a distributed company, we maximize the availability of travel options so that the onsite journey is not only relaxing after hours of traveling. Besides, it is helpful if you have a supermarket nearby when you run out of drinks or want to visit a pharmacy because of annoying mosquito bites.
• D) Options for activities — Another decisive factor is the possibility of activities for the free time within the location and the planning options offered by the immediate surroundings and nature. Officially, onsites are work. But come on, having a swimming pool in summer is a game-changer. And playing snooker or table soccer in winter encourages its own team dynamic.

In summary, finding the right location probably takes 1/3 of the preparation time. And I recommend taking this time. If you are searching for an onsite location, spend effort and invest your time. Otherwise, you always end up with a compromise. Today, we know almost 12 months in advance in which weeks we want to conduct onsite — this is helpful for the whole company as there is nothing more annoying than missing an onsite due to overlapping vacation plans.

Unfortunately, many great locations are not listed on the usual platforms (we tried really hard here 😅). In the end, it helped us to take a look outside the box. You can find incredible locations with unconventional ways of keyword research or speaking to peers. For instance, we found the location shown above by searching for isolated wedding places in Italy. In order to pick up the industrial air that surrounds our customers in logistics daily, we looked for old, renovated factory halls in Germany for the onsite last December. And I promise, there is nothing more fulfilling than seeing your colleagues’ eyes light up when they enter the location for the first time.

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2) Travel management: Agency or DIY?

Travel management is an exciting field. There is much operational potential hidden here. After many discussions, the picture quickly emerges that travel management can be outsourced very well: It does not burden your adequate planning time and creates convenient accountability with a service provider. However, in the end, it is a considerable surplus within your budget planning.

So far, we have kept all the travel bookings centralized in the organizing team. Yes, it meant additional planning effort, but it combines the advantage of perfect operability, allowing sustainability and budget thinking. For the first onsite, for example, we booked the flights of each team member to Italy, and we created squads for the corresponding rental cars to reach the final destination. With the doubling of the team size by May 2022, we kept the central flight booking but replaced the rental cars with organized coaches (this was a natural class trip feeling — pure fun!). With our last onsite we booked all itineraries centrally.

The great thing is that there is no full-service expectation. Every team member appreciates the organizational effort and wants to help. So, involve them, and the best stories emerge already during the arrival.
Our learning after the previous experience goes even so far that we can enable everyone to book arrival and departure. We may try this and provide just some guidelines as a travel policy.

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3) Food and drinks: Catering or Self-Service?

You booked your location and covered the travel management, so far so good. So, let us talk about the food and drinks. And this topic is critical (!) — nothing is worse than a starving crew. And how could it be otherwise, we experimented a lot while growing up.

I have already mentioned that onsites create a sense of belonging. This works well through spending time together, but our human side comes to the rescue here. Food and drinks connect; preparing and enjoying food together releases endorphins.

At our first onsite in Tuscany, we opted for a Self-Service+. We organized the entire catering and the associated purchase, and only the breakfast rolls were delivered freshly. We scheduled the days and bought accordingly. A note on the side: if you hate shopping as I do, finish it 1 day before the team arrives. Otherwise, it can be really, really, really exhausting…

Once on-site, the flow dictates. The most impressive thing about this catering organization was the unique possibility for everyone to find their role — running the bar, cleaning the dishes, preparing starters, making pizza, or taking over the barbecue. This was the most formative and bonding experience, but unfortunately, it does not scale well.

Reaching a new team size, we tried a mix of breakfast buffets and set a 3-course menu at the second happening in Italy. Lunch, drinks, and snacks were organized centrally by us. Operationally, the options were at a new level: The breakfast buffet allowed each team member to have their own morning routine. And the seated dinner opened up the setting for great table talks and team speeches. However, it lacks a bit of the charm of the community.

With the onsite in December 2022, we found our way into the triple daily buffet — breakfast, lunch, and dinner. Buffets offer the great opportunity of a central opening, yet they provide enough freedom for all tastes. In keeping with the back-to-the-roots theme, a prepared pizza bake was outstanding for the team atmosphere. It felt like handwork and the analogy to work’s daily build-up.

I have said a lot, so what is our learning? If it can be arranged, utilize the catering theme for team-building. Especially with teams of up to 25 people, pure self-organization is incredibly culture-building. If I ask, buffet over a set meal — more flexibility in terms of taste and time.

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4) Agenda: Set or Flow?

If you have reached this point, you are possibly 5–6 weeks away from the start. The organizational issues are bagged, and now it is about the content.

• How much time do we need as a company?
• How much time do the teams need?
• How much input can and do I expect from the team?
• Free time versus dedicated work time — striking the right balance

Questions upon questions. And here, too, we have probably not yet found the ultimate wisdom. What we did manage to do was to listen conscientiously. With our last onsite agenda, we achieved a 9.3/10.0 rating (a small ode to our orga team behind the scenes 🙂) and learned from our past misperceptions.

With the first onsite, we had a fallacy. We came together for the first time in the team constellation and saw it too myopic as a chance to solve all the current company topics: vision, values, goals, etc. And we were not able to achieve this. Don’t do this — really.

You want to avoid proactively timeboxing every hour of the onsite. The team will find it stressful if they jump from session to session. And you, as the organizer, will find it even more stressful if you can not stick to your thoughtful plan.

Some learnings:

• Schedule generously because you will always need longer and want to avoid breaking up intense discussions. For us, this means blockers for time without a program and an official start of the day from 10:00 am. If in the evening one or the other beer flows, you will need the later start — trust me.
• Allow “me time” and work time to co-exist. Going hand in hand with the previous point, people need their freedom — whether it is a time to retreat, mingle, write emails, or talk on the phone — that is individual, so give it to the team to get everyone involved. For instance, we block specific no-program times and share those slots in advance. So it is up to you to decide whether to use the time for yourself, keep time off or make calls and interviews.
• Let your team help shape it. You are not responsible for the entire agenda. Your team wants to spend time together to drive and discuss topics. I suggest enabling them and allocating appropriate sessions. Share the possible time slots with the team leads six weeks before them to think about.
• Set the official framework. When does the official program start? When do we meet? Where and when do we start and end the days officially? — Setting the onsite frame creates clarity for everyone — involving you. We do this by going through the agenda once at the opening ceremony.
• Share the agenda at least two weeks before the onsite. This is not about details but planning what will happen. It takes away many questions in advance.

In addition to the operational planning that can be optimized, several observations and patterns go hand in hand with an onsite.

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Some personal learnings along the way:

Getting out of your location, be it your personal or environmental comfort zone. The last onsite was the first time we organized a joint team excursion with individual program points outside the location. There was the possibility of choosing between sightseeing and a typical team activity or getting active with indoor soccer before meeting at a Christmas market. Again, we organized the arrival and departure centrally. This trip was one of the total onsite highlights across the board. So, we definitely will think about it again. Primarily, it could be an exciting topic for scaling teams to find the broadest possible denominator for the whole team.

Combine co-work with the official onsite. This may be only a topic for a remote-first company, but we have recognized that teams seek onsite time, and the initially planned onsite of 3 days may need longer. With the last onsite, we added the first-time co-working option and covered the accommodation and working area for the first two days. Overwhelmingly, almost 90 percent of the team accepted the offer, and even 60 percent arrived earlier at the weekend. The onsite officially started on the second day with an opening ceremony and dinner.

Communication will always be a challenge. The exciting thing about invitations is that they involve a certain amount of restraint. So most team members will be reactive onsite and wait to see what the “official plan” is. You, as the person in charge, are responsible not only for making sure everyone arrives onsite and has a good. You want to get through the days smoothly and well-managed. Embrace this role, speak up and communicate the expectations at all times. Take the opportunity at the beginning to set the golden principles for a successful team event.

Overarching, we stick to two golden principles during all retreats: be inclusive and never walk empty-handed. The first one is straight. You remember everyone on your value you already live up to. Help each other, especially new joiners, to get convenient with your company culture. The second one originated in the mentioned self-organization of our first offsite. The organization could only work if everyone has a sense of involvement and thinks collaborative. Everyone was asked to help the whole day by refilling the fridge, making new ice cubes, and placing garbage and empty bottles. We love the term!

On top, for us, it was precious to prepare a central, sharable source where all team members could read all onsite information in advance. Team members can find all information from the dates, participants, on-site or COVID rules, travel planning, location, packing list, agenda, and first contact points. After three times of the same question, what to bring, you wish for this medium.

Information gathering: In advance, for a smooth planning process, you need a lot of information from your team, including:

• Where are you staying at the time of travel?
• What food and drinks are preferred?
• Are there any medical peculiarities and allergies?
• Whom can we contact in an emergency?
• Which room partners do you want?

Before starting with the agenda and onsite planning, we gather all information with an engaging survey. This helps massively to access all details to make the trip as enjoyable as possible for everyone. Be a nag! Some team members will always have to be carried to their bliss until you have the answers.

Let people shine: A company onsite functions as a boiler room experience. You want to grow personally together. Running through your daily business, you may not find the time to celebrate successes and personal growth stories appropriately. We are using the company retreats to celebrate all promotions since the last onsite. Besides, we established our format to celebrate and honor those who stood out during the onsite event. We call them onsite awards and share 3 trophies in the final closing ceremony on the last day:

• The best team player
• The TradeLink enthusiast who shared the most knowledge about our vision, company, and market.
• The unstoppable party animal

Hardly any session brings so much commitment and positivity with it. And, insanely, there will be people competing onsite after onsite in the same disciplines.

‍Speak up: As previously mentioned, many set sessions need an opener. We use the opportunity to give short speaker slots for the founders and leadership in front of the entire team. This is an extraordinary opportunity to offer a stage for leaders, especially first-time managers. But, give your leaders a chance to prepare.

‍You cannot schedule parties. One of our first lessons is that team events develop their dynamics, and that is a good thing. Trying to steer the team in specific directions can fail. For example, we tried to get together on our first night in Italy and scheduled scheduled to enjoy some drinks calmly. It ended up being the most intense night of all. You cannot plan everything, but you can be prepared. In any case, take advantage of a proper music system. When the vibe hits, you do not want to have to slow it down with a lack of technology.

Stay flexible and let it flow. Even the best plan will not be achieved. You are already halfway there if you approach the planning and organization with this attitude. The flow and team dynamics will conceal all the planning, which may have gotten different.

Listen and learn immediately. You did it; it was great, and expectations were met — time to lean back. Not yet! You want to learn, understand your team better, and top it next time. Take the opportunity when everyone is still involved in collecting feedback. For example, we share the review survey already on the way home. With that feedback, this article came out the way it did.

A final thought on budget. In our planning, it has helped a lot if you set a budget target from the beginning and plan against it. We do this on budget per onsite team member. If it helps, our final cost split of the last onsite looked like this:

• 25% Travel
• 30% Accommodation
• 30% Food & Drinks
• 15% Activities & Merch

To carve out, I hope the article provides some valuable thoughts. We have not reached the final wisdom yet, so I am intrinsically interested in your experiences and would love to chat. Feel invited to send me a mail.Thanks to my colleagues Mareike Knappe, Anthony Piper, Frauke Ruthmann, and friends for proofreading and improving this article!

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Update June 2024:

We started to also create Wrap up videos from each onsite. You can check the more updated onsites and what we did here:

1. Tradelink Onsite No. 6 - Netzeband, Brandenburg, Germany
2. TradeLink Onsite No. 7 - Black Forest, Germany