There's No Such Thing As a Perfect Offsite


Liz Gray

Head of Community

June 29, 2023

June 29, 2023

June 29, 2023

So you’re building a remote-first and global team. There are a ton of perks to doing so, and there are also things that don’t come as easily. From personal experience, we can tell you that building and maintaining a sense of authentic connection across a team of 43 people in 9 countries (Argentina, Belarus, Canada, Pakistan, Portugal, Serbia, Singapore, Sweden, and the US) and across 11 time zones is a lot of work.

If you’ve worked in an office before and work remotely now, you know there are fewer shortcuts to take for building social connections with your colleagues. You can’t just turn around in your office chair and tell your colleague something you remembered. Video chats aren’t bad, but it’s still harder to read someone’s body language to determine how they’re actually receiving the message you’re trying to convey. 

This makes an emphasis on building healthy working communications and connections extra critical. 

We invest in getting as many teammates together as possible at offsites multiple times per year for this reason. It takes a good amount of time and effort to pull off, so we’re sharing learnings from the past several offsites we’ve held!

Visas Aren’t Readily Accessible for Everyone

It’s easy to take the power of one’s passport for granted. How many countries can you visit without a visa, as opposed to those that require you to apply in advance or upon arrival? What about your teammates? This can complicate who is able to attend offsites in particular locations. For example, several of our teammates need to apply for a visa to come to US-based offsites, but the timelines for the appointment to get an interview for a visa to the US vary, and US embassies and consulate offices are less accessible to some.


  • Check a site like Passport Index to get a better idea of what countries are most readily accessible to your team based on their countries of origin, and try to find locales with the least restrictions for the greatest number of teammates possible. 

  • Ask teammates if they have visas for additional countries/regions and include that in your planning.

Dietary Restrictions Are Important to Accommodate

Meals are a significant point of connection and of inclusion. If someone doesn’t have viable meal options, this probably means going out to find something on their own or sitting there awkwardly while others enjoy a meal. This leads to individuals feeling left out or overlooked and doesn’t contribute to a good sense of belonging. It also reduces time spent together with teammates if they have to go find something on their own.


  • Don’t assume that restaurants/caterers will provide reasonable options, even in places like California where you’d expect broader awareness and accommodation.

  • Trust but verify that vendors have a good plan (e.g. a plain plate of lettuce isn’t a sufficient accommodation of dietary needs).

Ongoing Communication Is Critical

Some additional observations in the broader bucket of “communicating is hard:”

  • Double-check that the vendors you choose accept online bank/card payments; dealing with checks can be really drawn out and frustrating for both parties.

  • You will have to repeat plans and expectations to the group at least five times more often than you think you need to for points to begin to stick (and it’s probably not personal, so get over it). Start by:

    • Creating a reference doc

      • Sharing that reference doc in relevant team channels

      • Sharing the doc via email

    • Sharing updates verbally

      • And formally (e.g. in town hall, at kickoff of week, at the beginning of each day)

      • And informally in conversations

    • Doing everything above again, just to be sure

Additional Tips on Logistics

  • Someone is going to feel unwell before the end of the week—from jet lag, general travel stress, or what have you—so it’s good to have a basic plan in place for supporting them when it happens.

    • Can you extend their stay a night if they need to delay travel? 

    • Do you have tests available to confirm/deny more contagious illnesses?

  • Poll attendees on challenges/issues that are front of mind and make space to address them in person (the highest fidelity communication medium possible is best for potential areas of conflict).

  • Be intentional about exposing people to different teams and perspectives; we’re all working toward the same goals but may have different priorities/checkpoints we’re measured by, and those can be significant points of conflict if you aren’t aware of the ‘why’ behind a different approach.

  • Don’t try to pack too much in! Go with quality over quantity of activities/experiences. This can include:

    • Planning a break mid-week for people to play games together or just relax

    • Not booking too many things that require transportation (twice in a week max) and/or change of venue

  • Put the most emphasis on time for collaboration/bi-directional communication; presentations and lectures can be done virtually without much signal loss.

  • Be explicit about what events are optional so teammates who need time to charge up or do focused work know when it’s okay to leave the group…and then reiterate that.

  • Ask teammates in advance if they have a need for specific accommodations (e.g. elevator access for mobility limitations, refrigerated storage for pumping mothers, etc.) which might require additional coordination with your hotel or impact event planning.

Offsite Planners: Please Read

This planning business is a lot of work, and you need to take care of yourself as part of the team you’re supporting with all of this effort. Be sure to:

  • Build time in for personal breaks/rest before, during, and after the event

  • Ask for/accept help sooner than you think you need it

  • Leave room for your teammates to figure certain things out on their own; you can’t and shouldn’t do everything for everyone all at once (and they’re adults, so they can handle it)

  • Ask for feedback—via survey or otherwise—and use that to inform your next one

  • Remember that you’re never going to be able to make everyone 100% happy; do your best and iterate based on feedback that’s given

So yeah, there’s no such thing as a perfect offsite: there are too many factors outside of our control. And that’s okay. All of the work is worth it if these events result in people having space to connect authentically and build healthy working relationships with each other. Keep building, be open to feedback on what worked and what didn’t, and iterate on your approach.

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