Plan a successful offsite for your remote team!

Does Your Remote Team Really Need an In-Person Offsite?

Honestly, yes, time in-person when you are a remote company can help your team stay aligned so that you’re all moving in the same direction and working on the most immediate and most important company goals. Offsites also give everyone time to build and grow relationships with each other so that company-destroying cultural problems never exist in the first place. We are always one team with everyone contributing towards the same goals.

Our CEO and Co-Founder John Cheng mentioned at the end of the offsite how refreshed the week made him feel and the team agreed. So much so that we have opted to add time monthly to meet in person for one day with a focus on company growth and strategy, giving us more in-person touch points between our quarterly offsites. We find there to be much power in an in-person offsite for a remote team.

How Often Should We Be Meeting for an In Person Company Offsite?

As mentioned, we like to run full offsite meetings quarterly for 3.5 days and will now be adding an additional 1 day for the months between. This is however no magic cadence. While I think the minimum would be once a year, especially for larger companies, teams should be meeting more frequently. Team offsite meetings can happen 2-4 times a year, depending on size and feasibility.

How Do You Plan an Offsite Meeting? 11 Tips for Hosting a Successful Offsite for Your Remote-First Company.

1.Pre-Work: Have Goals for the Offsite

Offsites are a dedication of time and resources (read: money) so it’s important to make sure that each offsite is planned with purpose and intent and not just something that happens because it has happened in the past and is now expected to continue. Setting goals for an offsite can be something large and lofty such as yearly or quarterly goal planning, or just spending time in-person to come together around set goals so everyone can understand where your company plans to go this year and come up with a plan to get there.

Because this is your time for your team or company to be in-person, be sure to prioritize deep, collaborative work that’s hard to pull off in a remote environment. Plan one or two goals for the offsite so that you’re not tempted to cram too much in. For a team that is normally remote, being together all day for a few days can be mentally exhausting so pick a goal or a topic that is important to your company (as will still be important by the time the offsite happens).

Whether a company or a team offsite, be sure that all participants attending have a shared interest in the established offsite goal and are invested in reaching the goal. People have to know how their work directly or indirectly impacts the offsite goal to be invested.

2. Pre- Work: Build a Solid Team Offsite Agenda

Building a strategic offsite agenda takes some time before the offsite happens, so be sure to have time set aside in the days and weeks before an offsite occurs to dedicate towards planning for your offsite.

Check in with the attendees and ask them for their feedback around the offsite topic/ goals you have come up with in step 1. That will give you a jumping off point for crafting a thoughtful agenda that will be effective. Be sure to ask each person what they are looking forward to getting out of the offsite as well - are there bottlenecks that are unforeseen by others? Are there things that have been going unsaid that should be discussed? Collecting this information beforehand lets you have a pulse on where things are, in relation to where they need to be by the end of the offsite to accomplish the set goals.

Once you know more or less what the leaders want to get out of the offsite (goals) and what the attendees want to get out of the offsite, you can begin to see themes and alignment. Sessions that are necessary to reach the goal should be assigned to the correct session leader from within the organization, likewise with sessions that are heavily requested by offsite attendees. Employees who are raising questions or issues that need to be addressed are often great choices to play a lead role in the session - whether that be the person who presents and leads the discussion, or for those who are more outspoken, perhaps a role of a “challenger” may be more acceptable so they can push back on the group discussion to make sure it is effective and arrives at a solid conclusion.

3. Stay on Track: Use a Facilitator

I have worked for many years and have been a part of many offsites and the one thing that really makes or breaks an effective offsite is how well it is facilitated. Dale is not only one of the best Executive Coaches we know, but he also facilitates our offsites; to use a tired expression, he is the person herding the cats of our company.

As a facilitator extraordinaire, Dale is the one who reaches out to start all the pre-work and planning, working with our company leadership to ensure we have good goals for the offsite, working with our employees to make sure they are leading the right sessions, and surfacing any bottlenecks or words left unsaid which need to be discussed.

While at the offsite, Dale keeps the conversation going by asking the hard questions people are thinking but don’t want to say as in “why is this important” or “how does this relate back to the company goals”. In short, he keeps us on track and most importantly takes notes and shares them after the offsite so everyone there can engage in conversation and be present in the discussion. Dale does this really helpful thing at the end of a session when we reach a conclusion or a stopping point where he says “It sounds to me like…” and will recap the conversation we just had including the decisions made so that we all know where we ended and are all on the same page.

A facilitator also helps with group dynamics. In larger settings some people may be more quiet than others and not necessarily pipe up in the moment. A great facilitator will create space in different ways for people who have different communication styles so that everyone can have their voice heard. This can mean calling on participants directly, reframing the question at hand to be more approachable or understood, or even bringing in new, related questions that will bring more viewpoints into the conversation. On the flip side of this, facilitators are also great at asking conversation monopolizers to let others have a turn.

You don’t need to hire Dale, but you do need to get your own Dale- a facilitator who has the context and knowledge of the company and its inner workings and whose role it is to ensure the sessions are successful, and thus ensure the offsite’s success ie we reach those established goals. This person can be in the company or outside of it, just be sure they really know the company and the players so they can be the most effective.

4. Start Off Strong: How to Kick Off an Offsite

There are many ways to start your offsite strong and what works best for your team or company will depend on many factors such as the size of the group attending and company culture. If you normally have a company all hands that happens remotely, you can replicate it into an offsite kick off. Be sure to share intentions for the week and get everyone excited about the days to come. HR teams for larger companies may be eager to use the kick off time to remind people about company code of conduct but that should happen before arriving to the offsite, perhaps at a prep session while still remote. You want to establish trust and confidence in participants to get the best out of them, not a feeling as if you think they will not behave as they are expected to.

At Baotris, we like to begin each quarterly offsite with a fishbowl feedback exercise. Before the offsite, each participant is sent a prompt asking them to come up with specific feedback for their team members: one piece of positive feedback and one piece of constructive feedback - the key is making sure it’s actionable and specific. We send in our feedback to our facilitator Dale who looks them over and has us correct anything that needs to be fixed and also aggregates all the feedback to send out after the offsite so no one has to take notes during the exercise. Then each person takes a turn sitting in the “hot seat” as the rest of their team members deliver their feedback to that person. The hot seat participant can decide how to receive their feedback - positive or negative first and is always asked if they are ready to receive feedback before we begin the session.

This is a great way for small groups to start their offsites because it establishes trust and communication from the beginning. Everything that needs to be said is done so up front and there are no barriers when having discussions or brainstorms later in the offsite.

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5. Be Session Smart: Using Time at a Company Offsite Wisely

Nothing could be worse for both the attendees and the company than an offsite that is full of boring presentation after presentation. Sessions should be interactive and thoughtful. You’re getting people together in a room for multiple hours - add up their salaries, that’s how valuable the session should be. The whole point of getting people together IRL is to facilitate communication and idea exchanges. Discussions, brainstorms, debates, these are all great uses of time because everyone can participate. Any background information needed can be sent around as pre-offsite reading homework OR can be a VERY small presentation at the beginning of the session to set the scene. If the topic and ideas are easily consumable, opt for the pre-reading to save valuable session time.

Another way to be sure to stay on topic and on goal for your session is to create a “Parking Lot”. Topics of discussion may inspire new ideas or topics that come up, however if the conversation goes off the rails, it is important that someone’s job is to call attention to it and “park” the new topic of discussion for a later time in the offsite or another time altogether.

Keep a list of parking lot topics - since you should have some buffer time at the end of the agenda (or end of the day), you can use that time to discuss any new topics that have come up that are either important to talk about soon or something people are interested in discussing. Any topics that come up that are imperative to the conversation at hand should be handled right then and there. Some parking lot topics can just be closed without further discussion.

6. Set Time Aside for Team Building and Rituals

Following on from the above, a great offsite agenda idea is to set aside time for intentional virtual team building. When your team is remote, there is less time spent bumping into each other in the kitchen or sharing a meal together so it is imperative that some of the time at the offsite is dedicated to offsite team building ideas that work.

Virtual team building activities do not have to be complicated or involve an escape room - bringing your remote team together can be as simple as taking time out of the day (end of the day is a great place for it) to express your gratitude for one another. Who deserves a shoutout for their work or for their impact on you in the last quarter/ year? Go around popcorn-style calling out that person and saying thank you for their contributions. Two rules here: be sure to be specific for what you’re thanking them for and leaders should be cognizant that everyone is getting at least some praise. If you are a leader and notice one person getting left out of this gratitude exercise, be sure to share some of your own that you have for them. For this reason, it is best if leaders prepare a gratitude call out or each member for the participating team.

Another team building ritual we have is focused around one of our favorite things - food. We’re a company of foodies who LOVE to eat and so we make sure each meal is thoughtfully curated both in the place we go (or order in from) as well as the family-style menu that we order. Just as meals serve as a time for people- family, friends, whatever to come together and enjoy a shared experience - meals are our way to put the work and strategy discussions aside as we nosh on some tasty eats. In fact, we love food so much that we end each offsite with a Food Tour of the area in which we are meeting for our offsite. Last week, we ended with a Downtown Los Angeles Food Tour, led by guide Nancy from Six Taste, a family-owned and operated food tour facilitator. The tour was full of delectable bites and historical facts as we walked around the sunny streets of DTLA. We can’t wait until our next LA trip to book them again - this time for the Koreatown tour.

7. Make Decisions and Hard KPIs to reach those Objectives

Sometimes people use the Parking Lot a little too much and will push off the final part of a session which is when decisions are made. Do not let this happen. The sessions should have an outcome, a clear pathway forward that everyone can commit to now that they have had their time to debate it. Session leaders, with help from facilitators, are responsible for determining the outcome objectives and their KPIs (key performance indicators) from the session if there is still debate going on by the time the session needs to come to an end.

As a follow up after the offsite, session leaders should come up with a roadmap to reach the defined KPIs and circulate to the group involved, as well as any stakeholders so that everyone can gain visibility into the new goals and the plan to achieve them. KPIs should be regularly referred back to when sprint planning as a way to always keep everyone’s mind on the ultimate goals and objectives your team or company is trying to reach. Including them as much as possible when assigning work and ensuring that all assigned tasks are inline with the KPIs guarantees that your team will always be working on what is important and not get sidetracked by shiny new projects that may pop up.

8. Make it Easy to Attend and Participate

There’s a lot of planning that goes into an offsite and I don’t just mean for those who are planning the actual event. Participants are people who have lives and families and need to make arrangements to join in so it’s important to start planning early and communicate dates and locations so that everyone can attend (whether in-person, or at the very least online).

A large part of the offsite planning process happens way before the event. First, a location and date needs to be chosen. The date should not only accommodate schedules for the attendees and those facilitating, but also needs to consider outside factors such as weather, pricing, holidays, and even other events happening in the area during that time.

Location should be somewhere that makes sense and can accommodate the group and the goals for the offsite. At Baotris, we will often choose a site based on elements such as where our clients are located (so we can meet in person), where our employees are located, ease of travel to and from, and of course, how good the food is.

Any other events such as restaurant reservations or team building activities should also be scheduled and communicated to the team in advance so they can be planned for as well. Employees may need to finish up work or have plans to meet up with friends locally or have a call with family in their off time so it would be good for them to know when that off time actually is.

Speaking of employees with families, there are often accommodation needs to consider for those with certain circumstances. Many of our employees have young children so if they need the family to travel with them, we make sure to help support however we can. We have even picked offsite locations to aid employees who had a partner who was expecting so they could be nearby in case needed.

Lastly, logistics - there should be ample power and wifi, comfy and varied types of seating and enough table space in any meeting rooms. Accommodations should be quiet and comfortable for a good night’s sleep and if sharing rooms, roommates should be decided ahead of time in a fair and logical way. Also always, accommodate those who need exceptions. Dietary information should be gathered and adhered to so that everyone has access to delicious and nutritious meals and snacks.

The most important thing to remember is communication is key. People have different experiences, needs, and backgrounds so knowing them will help you provide the best plan and back up plan possible. Share all the information everyone could possibly need to know, and then prepare for questions because no one will ever read the information packet you send out.

9. As Much as Possible, Step Away from Regular Work

There will always be customer requests and new fires to put out but for any inquiries that can wait until later - have them wait until later. The only way an offsite will be truly effective is to focus on the discussions at hand and participate as a collective team - unless taking notes, we have a laptops closed policy so no one gets distracted with emails or slacks that come in throughout the day.

Of course, we have a business to run and jobs to do. We try to leave some time at lunch as well as at the end of the day before dinner for people to take care of any work that needs immediate attention. And if anyone needs to step away, they are encouraged to do what they need to do, especially when customers are involved.

10. Take time to Reflect and do a Retrospective

Even if you have a dream offsite and can’t possibly imagine how it could have gone better, I bet at least one person attending has some insights about what could be improved for next time. Towards the end of the offsite, start to talk about whether goals were reached and get the team to start thinking about what sessions were the most successful and why, and likewise what were the sessions that were not as successful and how they could have been improved.

I think it’s a good idea to have participants start thinking about it but don’t hold the official retrospective until you’ve all had some time to think about it after. Doing a retro when you’re back in a remote environment is perfectly fine and while we are fans of doing it as a conversation, it is important to remember that some people won’t feel comfortable giving direct feedback so utilize your facilitator as a way for people to submit anonymous feedback.

11. The Most Important Part of an Offsite: Put the Plan into Action and Follow Up

The worst thing you can do is have a successful offsite with substantial objectives and well-defined KPIs only to let it all go to the wayside and go back to your day-to-day without putting your new plans to action.

It is actually a very common complaint that there is little or no follow-up and that progress made is only temporary. As mentioned above with how it’s important to refer back to the objectives and KPIs weekly and ensure all tasks are aligned to them, it is just as important to refer back to anything decided at the offsite and ensure there is a plan to bring it to action.

Asking session leaders to submit their session outcomes and roadmaps as a follow up to the offsite is always a good idea as it will build accountability into the process. Regular check ins on roadmap progress are good, but the more important the goal, the more visible the progress should be to the team and the company.

With the right amount of preparation and thought, and the right balance between strategic work time and team building, anyone can plan an effective team or company offsite for a remote team.