Why is it important to intentionally plan your company offsite? 

Bringing people together for an offsite can be a powerful and catalyzing experience – the benefits of an offsite are manifold and can include making tangible progress on company goals, and intangible benefits like improving team cohesion. Planning your offsite intentionally will help you realize these benefits.

It’s not a given that an offsite will be a success –  it can also be one of the bigger, more expensive flops that companies undertake. We often hear from our clients that they’re tired of wasting time and money and now they want expert help to ensure that the event is a worthy investment. 

PART 1 – Where to Start 

What are the “BIG QUESTIONS” to ask key stakeholders?

Identify the key stakeholders, and conduct 30-45 min interviews – to gather their perspectives. Ask clarifying questions, notice themes, and then start crafting your guiding principles for the event. 

Try to learn as much as possible before diving in – when we plan offsites for a client, we ask a variety of questions to gather perspectives on the goals, the priorities, and the organization. This conversation is not just useful for us, it’s helpful for the leader, too! Often, you might know you want to have an offsite but haven’t had a chance to think through the specifics. Here are some tried and true questions to help you prepare: 

• What do you want to feel, think, and/or say as you’re walking away after the retreat/offsite?  
• What does a ‘win’ look like? For you, your leadership team, and for the company as a whole? 
• If you could achieve just one business outcome, what would it be?
• How do you personally want to ‘show up’ as a leader? What qualities and intentions have you set for yourself this year, and how might this retreat help accelerate or support them?
• Looking back at past leadership retreats (at this company or elsewhere), what lessons and successes can we draw from or build upon?
• What concerns do you have? 
• Who else should we talk to?

Begin with the end in mind –  whether you are the leader convening the offsite or someone tasked to organize one, getting clarity about the answers to these important questions will help you make better choices about the direction to take. 

Why should you hold a retreat or offsite? Why are they important and what value do they provide?

The theme you select for your offsite can shape the value it creates – depending on who you’re bringing together and what is needed, you might choose a particular theme to guide and shape the experience – for example, celebration, alignment, or strategy planning.

Stepping aside from the day-to-day grind of work offers a unique opportunity – it allows employees to engage in deep thinking, solve challenging problems, and get to know one another better. Done well, there are both tangible and intangible rewards. Tangible rewards are what you probably think of – actionable outcomes that move the organization forward. Intangible rewards are less visible but equally important and often emerge from the interactions that occur outside formal sessions. Here are some examples of both:

What goals might you have for your retreat/offsite? What challenges or events do offsites help with?

Schedule offsites when you need to focus your team on broader goals and strategies – it allows your employees to disconnect from daily tasks and focus on high-level company goals and strategies. 

There are several key moments or situations when an offsite can be particularly beneficial: 

• Breaking down silos – building alignment and impactful relationships between different teams in your organization so they can work more effectively together 
• Navigating inflection points – creating awareness around an opportunity or making a particularly important business decision with a key group of stakeholders
• Integrating new team members or leaders – accelerating the integration process when there have been significant personnel changes in a team can be invaluable
• Building trust and figuring out how to work better together – providing a space for open and honest communication

Visualize the outcome you’re shooting for – give the decision makers a moment to imagine the ideal state at the end of the offsite. What do they want to take away from it? Is it a feeling, an accomplishment, or something else? This visualization exercise can help to identify common themes and goals for the offsite.

Set one clear and primary goal for the offsite – while there may be many potential goals for the offsite, it’s important to pick one primary goal to focus on. This helps to set expectations and ensure that the time is used effectively. You might have sub-goals, but you want one goal that sets the direction for the rest of the planning exercise. 

Plan time for reflection – make sure to allocate time at the end of the offsite for reflection and closure. This helps to ensure that the team leaves the offsite feeling satisfied and clear about what was accomplished. 

Part 2 – Logistics

What are some of the logistical questions you need to answer to plan your event?

With a better understanding of the big picture, it’s easier to figure out basic logistics – some of the questions you’ll need to answer to plan your event include:

• Who should attend the offsite? 
• When should you hold your offsite? And how often?
• How long should the event be? 
• Who should be involved in planning? 
• Should this event be held in-person or virtually? 

Who should attend the offsite? 

It depends on the type of offsite and its goals – naturally, the participant list is informed by the goals of the offsite. We typically see 3 different types of offsites: team, executive, and company.

Executive offsites benefit from depth of discussion, and company-wide offsites offer breadth – an executive offsite allows leaders to dig deep into the topic of choice and evaluate next steps. A full company offsite allows for a broader range of voices and perspectives and offers a chance for everyone to align on the same page. Larger groups are great for brainstorming around key topics, getting activated around a company rollout, building relationships or understanding cross-functional interdependencies. The smaller your group, the deeper you can delve into a specific area.  

Regardless of the type of offsite, leaders need to be deeply involved – before any offsite, it’s important to ensure the vision is on point, the context is appropriate, and the offsite will deliver on the team’s or company’s goals. 

When should you hold an offsite? And how often should you hold one?

Align the offsite with natural opportunities in your business cycle – regardless of the type of gathering, we recommend aligning the offsite with natural opportunities in your business cycle. While there may not be an optimal time on your calendar to take a step back, the goal is to find a time when team members can disengage from their day-to-day tasks and be fully present.

You might sequence activities within your offsite to allow for a combination of these – if all leaders are aligned and the company needs to get creative or come up with something new, a full company offsite might be the first step. The outcomes from this offsite can then guide the leadership team on how to organize and act on these outputs. Alternatively, the executive team may meet first to get alignment on the way forward in advance of a company-wide offsite. Understanding when to use different formats is key. Each kind of offsite has a different advantage and can be used strategically to benefit the company.

How long should you plan for your offsite to last? 

Most in-person offsites are 2-3 days long – it sounds like a lot of time, but it’s required to dive into a problem set, work through it, and then plan out the next steps that need to happen as a result.

• Plan 3-4 hour blocks of work for in-person offsites – you may have a block in the morning, followed by a lunch break and a rest period in the afternoon before the next afternoon block. This will help everyone stay energized and engaged.

• Build in breaks and protect energy with your scheduling – a lengthy mid-day break time with no scheduled activities will give everyone a chance to recharge, especially if people have traveled long distances. Different people have different energy levels. What might be energizing for some people may be draining for others. If you push your introverts, they will collapse. Take this into account when planning the length and activities of your retreat.

If doing a virtual retreat, plan for 2-3 half-days:

• Limit online retreats to 4 hours per day – if you’re planning an online retreat, don’t let it last more than 4 hours. This will prevent fatigue and ensure everyone stays engaged.

Who should be involved in planning a retreat/offsite? What external parties might you include? 

• CEO – ensure that the person in charge is fully invested in the process. They should meet with the facilitators to discuss the vision and objectives of the meeting. If the CEO or Founder is disengaged or merely checking a box, the meeting is likely to do more harm than good.

• Cross-functional stakeholders – pull together a cross-functional group of company leaders to guide the offsite design. This group can help identify the most influential people within the organization, understand the needs of different functional areas, and ensure the offsite is a good fit for the organization.

• An advisory group made up of “super participants” – peer influencers at all levels can be very helpful. This group can provide feedback for the offsite design, act as the eyes and ears of the organization, and identify any potential resistance or issues that may arise. The advisory group should meet two or three times before the larger event.

• External facilitators – professionals can help with offsite planning and execution. Most organizations underestimate the amount of time, energy, and experience required to pull off a productive offsite. 

• Executive assistants or travel agents – having an executive assistant to handle logistics such as booking hotel rooms and arranging transportation is key. If you have a large group, travel agents can help you find the best deals and ensure everything goes smoothly if something unexpected happens. 

Should this event be held in person or virtually?

Both are very good, viable options – virtual and in-person retreats can both provide value for your organization, which you choose depends on your goals for the event and your company context. For connection and building deep bonds, in-person is our style of choice. But it also takes more time, planning, and coordination – not to mention it’s more expensive!

It also depends on the location of your team you have – are you co-located full-time, working hybrid schedules, distributed, or fully remote? If you have a distributed or remote team, alternating between in-person and virtual formats is both economical and effective. The benefits of an offsite can still be achieved virtually with skillful and engaging facilitation. We’ve also seen companies that have gone remote decide to redirect their office space budget to in-person offsites. 

What other logistical considerations should you account for when planning an offsite/retreat? 

• Align the feel of the offsite with the company and employer brand – the offsite should reflect the current state as well as the goals of the company. For example, if the company is growing and wants to attract more mature employees, the offsite should reflect this by choosing a venue appropriately (as opposed to an indoor waterpark – and yes, we’ve seen this!).
• Consider the comfort and privacy of attendees – for example, if you’re an early-stage company and cash is tight, you might be tempted to have employees share hotel rooms. Think carefully about this – the cons may very well outweigh the pros in this case! We find that people appreciate having their own space to relax and recharge. Consider having participants arrive at the offsite a day early to give them time to relax, take care of jetlag, and prepare for the work of the retreat.
• If appropriate, consider inviting significant others – we’ve helped facilitate several offsites where significant others have been invited. Whatever you decide, make sure to communicate when they are invited and what the expectations are.
• Consider other locations that are more affordable than the US – it can be less expensive to fly your team across the Atlantic than across the country. One of our clients was shocked to realize that it was cheaper to bring the whole company to Spain than half the company to Palm Springs! Consider all options when choosing a location for your retreat.
• Communicate clearly and make the experience as seamless as possible for attendees – make sure everything is communicated clearly—including the schedule, location of facilities, and expectations for participation. 
• Pay attention to details – every detail matters, from the seating arrangement to the lighting. Make sure everything is planned in a way that fosters collaboration and engagement. Consider hiring a facilitator to help plan and execute the retreat. They can think of things that you might not consider and ensure everything goes smoothly.

Part 3 – The Deeper Dive

What does the offsite planning process look like?

Start early – depending on the size of the group, you’ll be glad to have ample lead time to find a venue, block calendars, and 

Get feedback – ask a sample of key stakeholders and participants what they want to see at the retreat, either through interviews or surveys. This will help you understand the expectations and preferences of your team and organization and can help identify what the organization is already doing well. 

Consider convening an Advisory Group – these sessions will help you design the retreat to meet your team’s needs and expectations. The flow of the meeting should be planned in these sessions. Present the agenda, discuss key strategies or methodologies, and make any necessary revisions. It’s important to remain flexible, as changes may need to be made right up until the offsite.

What does a good retreat/offsite agenda look like? What kind of activities might you incorporate? 

Companies are moving toward a more active and engaging approach to offsites – the traditional approach (treating offsites like conferences), is shifting towards a more active and engaging model. This shift is facilitated by professional facilitators who ensure a good flow of energy, keeping people engaged and connected. 

 Always keep the 3C’s in mind – these are the three main sources of value that people can experience when gathering for any event: 

• Content – the intellectual value provided during the event. People want to learn something new and useful! Our goal is to shift from passive to active engagement with the content – think less “keynote speech” and more small group conversations that promote active learning
• Connection – the social value created through deepening relationships among participants. We aim to create a safe environment for interpersonal risk-taking and to elevate participants to be part of the experience and get the mic in everyone’s hands. 
• Community – the communal value created, fostering a sense of belonging and pride in the broader group. The objective is to move participants from an “I” or “me” framing to a “we” framing, which promotes a shared purpose and unity of effort.

What kind of speakers or team-building exercises might you incorporate into your agenda?

Anchor with internal leaders and speakers – internal speakers, typically leaders with new initiatives to share, are often more effective at corporate events. They can lead breakout sessions, allowing attendees to choose based on their interests. The advantage of internal speakers is that they understand the company’s culture, goals, and challenges, and can tailor their messages to address these specific areas.

External speakers tend to be generic and expensive – if you decide to bring one in, ensure that their content is relevant to your company and your team—explain why it’s relevant and how it matters to the attendees. You could break up the speaker’s session to allow attendees to react and discuss the content. The goal should be to prevent attendees from shifting into passive reception of content.

What are the most important things to get right? 

Focus on encouraging active participation – don’t let people lean back and hide during the offsite. Find ways to break out into groups so that everyone can actively participate in the activities. 

Create a goal for your retreat – you should have one overarching goal that all of your activities are directed toward. You can have additional goals, but you should know from the outset what you want to have accomplished by the end. 

What are common pitfalls? 

Avoid overscheduling and draining attendee energy – you want all of the attendees to be at peak engagement and performance during the key moments of the offsite. To do that, you have to consider ways to provide time and space for attendees to recharge. 

Avoid dependence on consultants as facilitators – the aim of any consultant should be to leave the team feeling more capable and less dependent on them. If a team feels more reliant on a consultant after leaving, the consultant has not done their job effectively. Consultants should train the team on the methods and strategies they use, explaining the psychology and evidence behind each activity. This leaves the team better equipped to bring people together and collaborate effectively in the future.