Remote work brings many efficiencies, from eliminating commutes for employees to reducing real estate costs for organizations. However, having a remote workforce makes the times that the team gathers in person all the more important. Team offsites – dedicated, extended period of times where a team gathers outside of the office – may be the only time that remote employees engage in real life, and are prime opportunities for planning, reflecting, and bonding. Offsites are a big investment in both time and money… every team member is not only potentially traveling on planes, but also taking a break from their day-to-day tasks to participate in the offsite. Considering these costs, it’s important the team leaders put significant thought and planning into an offsite in order to get the most value out of it.
Given this is such an important topic, I enlisted the help of my friend Kirsten Newbold-Knipp, a GTM exec who has led sales and marketing teams of 5-50 people at companies like FullStory, HubSpot and Bigcommerce. Our thinking is aligned on the value of offsites and I’ve included some of her best practices in this discussion.
The last several leadership teams I have been a part of operated remotely, and we developed best practices to make our offsites effective. This article is a tactical playbook to help you run a great team offsite. While the examples are often referencing startups and scaleups, many of the insights are applicable for division offsites at larger organizations as well.
1. Plan every detail in advance, including a logistics schedule
If we are paying to fly people all over the place, we better have done our homework first. This includes the housing, food, discussion topics, supplies, travel schedules, etc. You may be thinking, “this sounds like too much planning, we can just wing it.” The dilemma is that when you are on the ground, and team members are arriving in droves, things get chaotic. We don’t have time to figure out the food, or realize that someone didn’t get a room booked, on the fly. Instead, it is much more relaxing when everything is figured out ahead of time.
To facilitate this at my last company, our Operations Manager, Kirsten Alexander, and I would create an extensive shared document for each offsite that contained all of the details I described above. It included a couple of key sections:
- Flight schedules: a list of attendees, their flight number, arrival time, etc.
- Car details: did we rent a car? All of the rental information is in the doc.
- Car logistics: are 3 people arriving earlier? Have them travel together.
- Meals: where are we going for each meal? Include reservations.
- Groceries: if we are at an Airbnb, what groceries do we need?
- Housing: what’s the address of the Airbnb? What’s the code to get in?
From a business perspective, it’s also important to think through the session agenda, how much time is being allocated to each topic and who is responsible for leading each discussion. Consider creating a “logistics schedule” that walks through minute-by-minute how the offsite will go. Here is an example:
This level of granularity accomplishes a few things:
- It forces you to think through the plan in advance, and avoids scrambling last minute.
- It ensures clarity and transparency for every attendee.
- It provides guidelines for time management (though you don’t need to limit a discussion to the scheduled time if it is going particularly well).
2. Spread agenda responsibility amongst the team
I break an offsite into “sessions” as illustrated in the agenda above – similar to a conference. Each session may be a different discussion or strategic topic that we want to tackle as a team. Some might be very active (e.g. brainstorming) while others might be more focused on presentation and feedback. To start, you can gather input from the team (via a Google form or live discussion) on what topics they are most interested in, and then cross reference that with your own priorities for the offsite.
If you are the team leader, your instinct might be that you need to do everything to plan and run the offsite. Instead, split the responsibility amongst the team so each person may be in charge of moderating a certain topic or session. For example, in the agenda I shared above, Neil’s name is highlighted next to the “Competition Review” session we scheduled. As the owner of that session, he is responsible for:
- Planning the session: what are we discussing and aiming to get out of it?
- Creating materials: if we need slides, he creates and presents them.
- Moderating: keeping the conversation focused and taking notes.
- Following up: identifying next steps and coordinating with the team leader to ensure they are acted upon.
You may consider giving team members specific constraints in creating a session. For example: include lots of customer artifacts (e.g. call clips, webinar clips) or include an interactive element (team should get up on their feet at least once). Ideally, each team member has flexibility to build the session however they see fit.
Regardless of how flexible or specific you are in setting the guidelines for the sessions, by spreading the responsibility, the rest of the team will feel a sense of ownership for the offsite. Plus, this approach takes lots of work off the team leader’s plate!
3. Set expectations
Prior to the offsite and at the start, it’s crucial for the team leader to share context on why we have gathered, why this time is so valuable, and what we aim to get out of it. Some items to consider communicating:
- Share clear goals: everyone who is attending an offsite should have clarity on why it is being hosted and what the objectives are to achieve.
- Be prepared: create session materials in advance, not the night before.
- Review other’s session materials: if materials are prepared in advance, everyone should read them so they have context prior to each session.
- Plan for your day job: ensure that out-of-office plans are set so people that will be unavailable during the offsite have their jobs covered.
- Communicate with leaders’ teams: if this is a leadership offsite, ensure each leader communicates with their teams that they will be relatively unavailable during the offsite.
Kirsten confirmed how important having “pre-reads” are – i.e. prepared slides or session outlines that the team can review in advance. She highlighted that we want to avoid an offsite where much of the time is spent “being presented at.” Instead, the time is far more valuable when everyone comes in with context and can spend the offsite having strategic discussion, gaining clarity and reaching consensus.
4. Make space for breaks, but protect the offsite time
One of the difficult parts of attending a team offsite is pulling away from one’s day-to-day responsibilities. This can be particularly difficult for leaders, whose teams may be relying on them for input. However, offsite time is special, it doesn’t happen that often, and needs to be protected. There are a few ways you can do this:
- Schedule 30-60 minute breaks every few hours of sessions
- Have a 60 minute lunch break
- Include buffer time in the early evening before dinner
- Do “walk and talk” breaks – Kirsten found that her exec team loved these at a small offsite
During these breaks, the team leader can encourage the group to check in with colleagues, respond to critical messages, or take a call. However, outside of those time windows it’s important to enforce that the team’s focus needs to be at the offsite, and other matters should wait unless they are extremely time sensitive. Team members frequently taking calls and excusing themselves during sessions undermines the point of gathering everyone in person.
You can encourage cooperation by sharing the agenda ahead of time, so team members can schedule important calls during the breaks.
5. Consider the physical space for team bonding
Team offsites are important both for the clarity that they bring, and also the community that they build. A part of that community building is the space that the offsite is hosted in. As Kirsten pointed out, “CEOs realize that employees don’t want to just sit and stare at each other in a windowless conference room – today’s teams seek inspiration in both their personal and professional lives.” The right offsite space will depend on the size and culture of the team. For small, tight knit teams, a shared house (i.e. Airbnb) works well for a few reasons:
- It feels more relaxed and less “stuffy” than a hotel
- It often has private space for activities (e.g. a backyard with a firepit)
- It enables the team to eat breakfast and lunch at home, often saving time and cost
I recognize that for larger teams, a shared house becomes impractical. At one of Kirsten’s early-stage startups the exec team rented an entire bed and breakfast. This provides many of the benefits of a shared house, but ensures team members have more personal space and some privacy. Boutique hotels nearby a private meeting space could work well for teams at larger companies or even getting a block of hotel rooms and working with a local venue for more creative space is viable.
If you decide to go the Airbnb route, consider some of these variables:
- Does everyone have their own room with a private bath?
- How close is it to nearby restaurants? Ideally a 15 minute drive max.
- How close is it to the airport? Ideally a 30 minute drive max.
- Does the living room have ample seating?
- Does the living room have a large TV that can be used for presentations?
- Does it have outdoor hangout space? A firepit is a great social hub.
- Does it have a kitchen that you can use for cooking breakfast and lunch?
- Do you have access to the thermostat to ensure the room is comfortable?
- Does it have an interesting view (e.g. waterfront, near mountains, etc). This is certainly not required, but it is nice to have!
In addition to the physical space, also consider the geographic location. If it’s winter, the team may really appreciate an offsite in Miami. I try to vary the locations for each offsite both for novelty and to make things fair for the remote team that is traveling in from many different locations. If someone who lives in California has to fly to Miami for the offsite in Q1, they might really appreciate if Q2’s offsite is in Denver, a much shorter flight.
6. Don’t skimp on the food
This one is simple but important – stock up on food! For many team members, these offsites may be one of the few times they are traveling during that month/quarter, and the experience should feel like a treat.
A high impact, low cost tactic is filling the kitchen or meeting space with great snacks. The offsite can be a time to indulge, and binge on some snacks they might not normally eat at home. Get the chips that aren’t the healthiest but everyone loves to occasionally eat. Those little things make a big difference. At my last company, we got frequent requests for “flaming hot cheetos,” an obviously guilty pleasure among members of our team!
Outside of snacks, meals can be a mixture of catered in or taking the entire group to a restaurant. Be sure to make all reservations well in advance. “Consider team members who are vegetarians or who may have food allergies. Figure this out ahead of time so you aren’t scrambling during the offsite,” notes Kirsten.
If possible, have lunch either cooked at home or catered in. This is beneficial for managing cost and maintaining focus. An offsite has a packed agenda, and having everyone out for a 1.5 – 2 hour lunch is not the best use of time. Instead, dinner is often the best time to take the team out, so it is less disruptive to a long day of sessions.
I like to use dinners as the primary “going out” portion of a team offsite, whereas the other meals are functional to keep people fueled during an intense day of sessions. This is an opportunity for high impact – consider finding unique restaurants that will be memorable. With that said, be flexible. I was surprised that at a recent offsite for my leadership team, everyone was so exhausted at the end of the day of sessions that the vote was to actually order in rather than do a big dinner out. Just go with the flow!
7. Get the right supplies to keep the team focused
Be sure to think through what tools you may need for the offsite, because you don’t want to be running to the store during precious meeting time. These might include:
- Giant sticky white boards for brainstorming
- Access to a large screen TV
- Connectors to ensure laptops can stream slides / notes to that TV
- Sticky notes
In order to keep people focused, limit laptop usage, or request that everyone logs out of Slack and email, and only uses laptops for note taking. This time is precious, and we want to minimize distractions. Using pen and paper for certain activities can help do that. To be sure, it also may be most efficient to take notes digitally, and that can often be delegated to one person for each session.
8. Don’t feel pressure to plan fancy events and experiences
Some team leaders and planners assume that an offsite needs to have “fancy / speciality” events or experiences in order to be valuable for the team. For example, at one of my team’s offsites, we took everyone to a cool indoor mini-golf course. It was one of the higher cost items on the offsite budget. When we surveyed the team afterwards, we found it was actually something they valued the least, and instead it was the time spent simply sitting around the backyard fire pit that they valued more.
This does not mean you shouldn’t consider a speciality event or experience as part of the offsite. Just keep in mind that the team is there to bond, build trust and get work done. Having good food and good spaces for people to talk tends to accomplish 90% of that goal.
Kirsten’s #1 goal for COVID-era offsites has been building community – in a world where many team members have never even met – that common bond makes everything else in a team easier. Even if everyone leaves the offsite not digesting any of the business content, but still builds trust and deeper bonds (i.e. a stronger community), the investment was well worth it.
9. Summarize the key takeaways and lessons learned promptly
Attending a team offsite is like drinking from a firehose. So much information is being shared and discussed, so many conversations – it can be overwhelming. To ensure the conclusions reached during the offsite are not lost in the shuffle, it’s important to quickly organize all of the notes taken and call out action items.
At my recent offsites, we created one primary notes shared doc, and contributed all of the session notes into it. Then, often on the flight home, I go through those notes, pull out key takeaways, and create a summary at the top. I then send a follow up email to all attendees with a link to that document.
In addition to the business takeaways that may be included in that summary, consider writing down all of the lessons learned from running the offsite on the flight home while they are fresh in your mind. Everything from pros/cons of the lodging to what food was most popular to how accurate your scheduling was. These insights will be invaluable when you are planning the next offsite.
Finally, consider sending a post-offsite survey to all attendees to gather fresh feedback on their perspective of the event. This can include tactical items (e.g. was the food good?) to session feedback (e.g. which session was most impactful for you, and why?).
10. Create a rhythm for offsites
As you start to plan more offsites, consider having them on a regular cadence. For a leadership team, quarterly is my preference. For other teams, at least twice a year tends to work well. Having offsites on a regular rhythm can also help the team plan, both for their personal travel and to ensure that events don’t overlap major projects / deadlines.
An important note – if the offsite includes folks in sales, be sure to not schedule it at the end of a sales period (e.g. the last week of the month or quarter), as this can add unnecessary stress to that team.
Team offsites are an increasingly important way to build culture and cohesion amongst a team that is remote or hybrid. Kirsten shared a fascinating stat about this: “74% of companies are already or are becoming hybrid/remote in the next 5 years.” Additionally, she noted that according to Amex Travel, team meetings are the fastest growing type of meeting, and the per attendee budget is growing at 73%. All this is to say that team offsites are a major line item, both in cost and time. It’s worth the effort to get the logistics and the content right.