How to Make the Most of Your Annual Offsite

What we’ve learned from hosting two offsite trips. Spoiler alert: it’s worth it.

Maya Shenoy
Inheaden
6 min readJun 2, 2023

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Picture this: it’s a random Thursday afternoon. You’ve had a little too much to eat at lunch so you’re sleepy, the aircon isn’t working so the room is hot and the office has run out of your favorite snack.

And the only thing you have to look forward to is a 3-hour long hybrid meeting to discuss the company’s 5 year plan.

Realistically, you and your fellow team mates are not going to be bringing your best ideas forth. The innovative spirit and problem solving mentality you need to make this meeting dynamic and effective will be at an all time low.

Naturally, we have a solution for this — an offsite trip.

Simply put, an offsite trip is one that is organized and hosted by a company wherein they bring team members from around the world to a common location. The length of the trip can vary based on meeting objective, number of members involved, budget etc. and the goal of the trip is determined by the company. Some common goals can be planning the 3-year or 5-year plan of the company, brainstorming new products and strategies or even a trip dedicated to bonding and having fun as a team.

There’s several benefits to hosting an offsite trip.

  • It removes you from your usual environment, which automatically pulls you out of your comfort zone
  • It offers you an opportunity to focus on the big picture of the company, without being hindered by the day-to-day tasks you must complete
  • It is a bonding experience for the entire team, especially if your company works in a hybrid or mostly remote setting
  • It’s an environment that allows you to have some fun after work

Sounds great right? Well, it’s not really that simple.

The thing about hosting an offsite meeting as a startup or SMB that doesn’t have a committee dedicated to planning events is that YOU have to plan it. We all know how cumbersome it can be to plan a vacation, so imagine the hurdles faced when planning a trip that involves several individuals from different parts of the world. The Inheaden team can tell you from experience that planning an offsite starts months in advance and after 2 different trips, we’ve learned a lot.

And we don’t gatekeep, so we’re going to share a checklist of things to tick off while planning your offsite.

It’s also worth mentioning that an offsite trip is no less important for a fully in-person team. Even if you’re taking everyone an hour outside of the city to sit down and chat, it still counts and achieves the same conditions that makes an offsite effective.

Start planning 6 months in advance

From a budget standpoint, the earlier you plan the better. Tickets are cheaper, accommodation is easier to find, and you have plenty of time to agree on a mutual location. The other reason is so everyone can plan their vacations, family time and other commitments accordingly. Penning down the dates gives your team the time to plan their own time.

Also, given the load of your own day-to-day tasks, you will need time to plan the trip from start to finish. 6 months sounds like a lot, but it’ll go by a lot quicker than you think.

Check visa requirements for all visiting members

Your offsite location should be easily accessible to all team members that are attending. Certain countries offer visas that are quite expensive and difficult to obtain. Others are open to most and easier to plan for. Don’t forget to check with everyone before locking in your location.

Plan the agenda meticulously, and be ready for it to still go off plan

It might sound counter-intuitive to plan for something knowing it will probably not go according to plan. But from our experience, it is better to have a plan to refer to than winging the entire thing. Often times, workshops and meetings will go on for longer than desired, but with a plan you can still cover the most essential topics and make the most out of your offsite trip.

Flexibility is key for a good offsite. But flexibility without structure is often just pure chaos.

Figure out the food

You will need a minimum of three meals a day + snacks and beverages. Don’t forget to pencil in time to get groceries and order in food while planning your agenda. Be sure to check about allergies and dietary preferences from the entire team ahead of time to streamline the ordering process.

Cooking together can be a great bonding experience. If your accommodation comes with a grill, a barbecue is a great way to cook and enjoy some great food as a team. You can also try baking or cooking dishes from your culture for others to experience.

But remember, everyone should also be involved in the cleaning process.

Make your expectations very clear

Offsite meetings can serve different purposes. Every company has a different take on how and why they want to host an offsite meeting, so it only makes sense to let all visiting members know what to expect. Some offsites are just for fun and bonding; others are meant to be a time dedicated to planning and strategizing. Be blunt about the expectations and goals to be met at the offsite so they know what to expect and aren’t disappointed or frustrated by the actual trip.

This is especially important for first time attendees.

Take board/card games with you

Working after dinner is usually not the best idea. But it is the perfect time to bond over some games. Avoid console games and screens because they’re usually not as interactive and personal as other in-person games.

The fun part about having a multi-cultural team is teaching and learning new regional card games.

Offsite trips can be stressful to plan and execute, but the outcome is worth all the effort. If done well, your team will leave the trip feeling invigorated and inspired. Be sure to take your time planning the trip, keep various members of the team involved in the process, and learn from each experience so you can make the next even better.

The Inheaden Leadership team during our offsite to Bodrum, Turkey’23

What would be your dream offsite trip location? Let us know in the comments ✍️

Thank you for reading!

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We are a fast-growing tech startup headquartered in Darmstadt, Germany. Incepted in 2017 by 3 co-founders, we now have a team of 20+ experts in Information Technology (IT) and Digital Product creation. As Europe’s first Tech Angel, Inheaden supports startups or small businesses by providing them with the strategy, assets, and maintenance they need to thrive in today’s digital era.

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Maya Shenoy
Inheaden

An engineer by degree, but a writer at heart.