Our EAs have set up dozens of offsites for some of the fastest-growing startups in the United States. We gathered the top learnings and created a structure and process that will save you valuable time by applying them to your own company offsite.

Why should you host a team offsite?

Having a clear reason to host an offsite meeting can also give you more clarity on agenda planning and expected results.

Planning a company offsite requires a considerable amount of effort, resources, and time, and the benefits of an event of this nature can greatly benefit, not only your team but your company as a whole.

Before you dive into full planning mode, ask yourself: how can an offsite benefit my team? Here is a list of potential reasons you may want to consider hosting an offsite:

• Set commercial goals
• Focus on product development
• Team building
• Decide on projects for OKRs
• Gain business context

One of our customers, a startup with over 350 employees based in San Francisco, asked one of their Viva executive assistants to plan an offsite for one of their teams. The EA designed a flawless event for the customer experience function: a team of 27 people scattered around the Americas, EMEA, and APAC.

As this was the first full-team offsite, one of the main goals was to build camaraderie and make these 27 individuals connect with each other during the three days of the event. The executive assistant in charge came up with an ice-breaker activity called “Poncho board”: a personalized space in which everyone could write messages for each other, telling them how much they learned from them during the offsite, and how thankful they were.

This is how the EAs poncho board looked like at the end of the week: full of thoughtful messages from every team member who attended the offsite.

If the objective of the event is talking about your Go-to-market motions with your executive team, make sure everyone is aligned on the common goals and the changes that 2023 is bringing into your business. Make a tactical plan that allows you to see how each team will contribute to getting there.

Another great use of time while in an offsite, is to focus on product development. This environment serves as the perfect platform to come up with new features or even launch products by meeting in person to discuss creative ideas using attractive visuals. Big announcements are even more impactful when your team is present to share the excitement

Putting your entire team together with one objective only is the ideal scenario for brainstorming and designing new advertising campaigns. When your creative team comes together, better ideas are born.

Who should come to the offsite?

The attendee list should be completely aligned with the objective of the offsite and the goals you’re hoping to achieve. Take your main objective and think about who can help you deliver that message and get closer to that objective. If the reason you’re having an offsite is that the sales team did an outstanding job in Q1 and you are now planning on setting new goals, consider inviting the president’s club to the event and leaving other departments out of the mix.

It’s best to have a smaller group of key individuals collectively working towards the same goal than a large group of team members without a clear reason to be there. The question you should ask yourself before concocting the guest list is: who can help me achieve The company’s goals and how?

External guests

One reason you may want to consider inviting external guests is that using an offsite as a learning opportunity for the members of your team can help them upskill themselves and as a result, be able to provide even more value to the company. Identify areas of improvement and find industry leaders or speakers that can help your team get up to speed on new trends, strategies, or any other specific knowledge that you consider valuable.

A way of doing this in a more budget-friendly way is to not necessarily hire an external contributor, but appoint one of your own team members as the expert on a specific matter. They can be in charge of teaching a session or sharing key research to benefit the rest of the attendees.

Assign someone to run the event

Despite the specific goal of the offsite, one thing is true to any corporate event: if you’re not mentally present, there is no point in going. That’s why you need to make sure there is one person that can plan the event from beginning to end and ensure its execution is going according to plan, without you having to worry about logistics during the offsite. Any distraction that gets your attention away from the offsite defeats the purpose of having one.

Our recommendation is for you to assign this responsibility to an executive assistant. Their organization, attention to detail, and problem-solving skills are decisive factors that can be all the difference between an impeccable event and a turbulent one.

An EA can start planning in advance. They will dedicate their undivided attention to the logistics and make sure everything runs smoothly and on time. The venue, catering, materials, swag, and everything in between require a lot of attention to detail.

This is what you need to do to make it happen

When you plan a company offsite you cannot just “wing it”, there are many things to consider and schedule, and something as little as not making a reservation on time can get in the way of your vision. We have grouped all of those components into three main categories you cannot let slip: set a budget, plan your agenda, and take care of the logistics.

Set a budget

One of the most important things to consider when planning an offsite is determining the budget for the event. To start answering that question ask yourself this: how can I make our dollar go the furthest while still making productive use of time?

These are the six main expenses for any offsite:

1. Accommodation/Location: If possible, avoid major cities and high season (they tend to be more expensive).
2. Co-working space: It’s one of your fixed costs, so see it like this: the bigger the group, the cheaper it becomes per employee.
3. Number of people: Think about the variable costs, such as catering or swag. A limited guest list equals a smaller expense.
4. Guest speakers: Is it worth hiring an external contributor or can someone from your team take over?
5. Transportation: The two biggest transportation expenses are plane tickets to reach the location and transportation between accommodation/location and co-working space.
6. Team activities: Collective experiences are the key to a friendly budget. If you do choose a big city (because the majority of your team is there, for instance,) there are some budget-friendly options. Even in an expensive city like San Francisco, a cruise through the SF Bay is only $48 per person.

According to Moniker Partners, the average corporate retreat cost in 2023 is US$4,000 per person for around a four-day retreat, which means you need to budget US$1,000 person/day. Now the question is: how much of that budget goes to each thing? Theoffsite, suggests that the main expenses are distributed like this:

The number of people, location, and many other factors determine what the budget might look like for you and it can vary greatly from one startup to the next one, but the percentages are an indicator of what your future event may cost. The following is a real example from one of our customers. This budget didn’t include plane tickets or accommodation, but the executive assistant managed to arrange a 3-day offsite for 27 and spent less than US$6,000, only US$250 per person.

Plan your agenda

With a clear set of objectives and a carefully curated invite list in place, the agenda serves as the roadmap that guides the discussions and activities throughout the offsite.

Allocate an appropriate duration for each topic, somewhere between 45 minutes to a maximum of two hours. This time frame allows comprehensive discussions without rushing or diluting the content. By sticking to this guideline, you can cover four to six meaningful topics within a full day, maximizing the efficiency of the offsite.

When designing the agenda, it is vital to consider several key elements. Firstly, outline the specific topics of discussion that align with the objectives. Each topic should have its own clear objective, outlining the desired outcomes, whether it is discussing leader direction, deciding on strategic goals, or debating areas for improvement. Additionally, determine the types of activities or delivery modes that will be employed, such as small group working sessions, large group facilitated discussions, brainstorming sessions, panel discussions, Q&As, or team building activities. Some examples are:

Once you have the definitive agenda for the event, share it with the attendees the moment you have everything confirmed, over-communicating can never hurt. Plus, that will leave some buffer time so they can anticipate what’s coming, educate themselves on the topics, and make much more meaningful contributions. Especially for the ones that will be appointed speakers or Q&A moderators.

Take care of the logistics

Good logistics go unnoticed sometimes because a high-profile event has to meet high-quality standards. but what if the audio from the new commercial wouldn’t work? And what if nobody thought of ordering food? Now you have a hungry team that is getting impatient.

That’s why logistics are crucial, they are the invisible thread that creates a cohesive event where everything just works. There are five main things that your executive assistant should plan for:

1. Presentations Design a kick-off presentation to welcome everyone on the first day and make sure all the files are on the cloud, backed up in a common folder you can access anywhere, and ready to play.
2. Equipment Think about all the materials you’re going to need: laptops, projectors, speakers, and designate someone to be in charge of taking them to the location.
3. Food and beverages We cannot emphasize this enough. The catering coordination is something you want to make sure is done in advance and reconfirmed to avoid any potential hiccups.
4. Swag (budget permitting) Show your team how much you care by giving away some company swag. Think backpacks, water bottles, sportswear, etc. Seeing their reaction live is priceless.

When to schedule a company offsite?

When setting the date for your offsite, there are several factors to keep in mind to ensure a smooth and well-attended event: the commercial calendar and industry-specific events to avoid any potential conflicts that may impact the availability or increase costs. Check for holidays, conferences, or major industry gatherings that could clash with your desired dates.

Take into account the availability of hotels and any travel considerations, such as visa requirements or vaccination mandates. Communicate with your guests in advance to understand any scheduling constraints they may have.

Our recommendation is to start the planning process at least two to three months in advance. This timeline leaves enough buffer time to choose everything from co-working space, agenda development to communication with attendees.

Starting early also allows you to engage your team and gather their input, fostering a sense of ownership and ensuring that the offsite aligns with their needs and expectations.

When determining the frequency of your offsite events, it’s essential to strike the right balance. While it can be tempting to schedule them frequently, it’s important to consider the practicality and impact on your team’s productivity. For most startups, an annual offsite can be an ideal cadence, providing dedicated time for reflection, strategy, and team building.

Offsite learnings

Hosting an offsite for your startup team brings numerous benefits. Team building activities are not only fun for your employees, but they also improve professional relationships. When the members of your team spend time together, they get to know each other better. This leads to a better understanding of one another and a better outcome on the professional side.

Make a concrete plan for each objective identified during the sessions. Setting goals without a plan can lead to unfulfilled aspirations and missed opportunities for growth. Once the offsite ends, it is vital to establish clear accountability and follow-up mechanisms to ensure that the plans formulated during the event are put into action. Assign responsibilities, set deadlines, and establish a system for tracking progress.

A good way of evaluating the success of the offsite is to gather feedback from participants. Conducting a survey after the event allows you to collect valuable insights, understand what worked well, and identify areas for improvement.

By actively seeking input from your team, you demonstrate a commitment to their opinions and create a culture of continuous learning and growth. Use the feedback received to refine the structure, content, and overall experience of future offsites. Implementing changes based on the survey results not only enhances the value of future offsite events but also shows your team that their input matters.

Check out the questions we recommend asking after each offsite to ensure your next one is equally if not more successful:

• How satisfied were you with the content proposed throughout the off-site? Do you feel we accomplished our objectives?
• What was your favorite working session? Help us understand with a short explanation.
• Which session would you cut next time? Help us understand with a short explanation.
• How would you rate the flow of the off-site? (Overall agenda, session lengths, breaks, ticket handling slots, activities…)

Once you’re back at work have a retrospective meeting with some of the team members that took part in the offsite and come to conclusions as to what went well, what could’ve gone better and the lessons learned. Gather feedback from team members and ask your executive assistant to codify those learnings so you know what works best for you and your team.

Download our free, completely customizable Notion template and plan an Offsite your team will never forget.