How To Plan A Great Strategic Offsite Team Meeting
So, you’re planning an offsite meeting — congrats! Whether it’s your first executive offsite or one of many, taking some time away from the everyday workplace routine is a great opportunity to reflect and reset.
A company offsite isn’t just another team meeting. An offsite can accomplish different things in different ways than onsite meetings. It signals to everyone attending that this is something beyond ordinary day-to-day operations, from the environment to the meeting’s purpose and the strategic goals you want to achieve.
When done right, leadership offsites can have a lasting impact on your executive team, helping you gain fresh perspectives, recalibrate your business strategy, and head back to the office with clear objectives and action items.
Regardless of your specific industry or company stage, there are some essential steps for planning a successful offsite: defining your desired outcomes, designing a clear agenda, choosing the right location, and structuring team-building activities that foster collaboration and spark creative thinking.
Whether you’re booking strategic planning offsites, launching new products, or building trust after a reorg, here’s the blueprint for an impactful leadership retreat.
The First Step: Define Your Desired Outcome
Before you even think about booking a conference room or creating event budget templates, answer this question:
What do you want to be different by the end of this offsite?
A well-designed off-site meeting starts with the end goals and main benefits in mind. Do you want to align the leadership team around strategic goals? Build trust after a merger or executive transition? Finalize your business strategy for the next year? Spark new ideas for innovation? Or do you just need to boost sagging morale?
Think about what you want people to feel, think, and do after they leave. This will help you shape every decision that follows, from the meeting agenda to the team-building exercises.
Create an Agenda to Match the Mission
Once you define your desired outcome, reverse-engineer a clear agenda for your retreat. Here are some common focuses for a team offsite:
Strategic Planning: Annual strategic planning meetings are common. Use this time to review the past year, align on long-term goals, conduct a SWOT analysis, and develop strategic objectives.
Team Building: If the management team is new (or struggling), build in dedicated team-building activities and social events to help people connect outside the workplace context. (The best offsites are the fun ones, no matter how high on the leadership ladder the attendees are.)
Professional Development: Bring in a good facilitator or engaging keynote speaker to enhance your employees’ skills or explore different ways to tackle common problems.
New Product Kickoff: If you’re about to launch the new product that could define your company’s trajectory, use the offsite meeting to build excitement and to clarify any potential confusion or concerns.
Regardless of your specific focus(es), always make space for open discussion, breakout sessions, and both larger group and smaller group activities. Provide plenty of variety throughout your agenda — this will help keep energy high and make everyone feel included.
Choose the Right Location and Meeting Space
The external environment matters more than you might think. Your chosen meeting space sets the tone and influences people’s energy levels — it can either stifle or inspire creative thinking. Consider the type of corporate retreat you want:
Nature Retreats: If you want to promote reflection and connection, having your retreat in nature can foster deep strategic thinking.
Swanky Hotels: A fancy hotel is perfect if you want to treat your senior leaders to a luxury experience while also remaining focused on productivity.
Corporate Retreat Facilities or Event Centers: These typically have built-in AV setups, breakout areas, and break room amenities. They’re often convenient, especially for large retreats, but to some, they can (understandably) feel a bit too similar to being at the office.
Ambiance, structure, and setup all matter a lot. Think through this part! Overlooking it can lead to disaster. Avoid cramming people into a dank, dark, windowless room. Instead, choose a bright space with plenty of natural light, room to move around, places to write (whiteboards and easels), and, obviously, fast internet — unless you’re looking to unplug with intentionality.
If you have remote team members who can’t attend in person, consider offering hybrid virtual strategic planning sessions. While these don’t offer the same bonding experience, they’re an affordable way to include everyone on your team, whether they work in the same physical office or not.
Logistics Are Everything
The devil’s in the details, and you’ll need someone who can handle them. That could be you, or a meeting coordinator, or a dedicated event planner. Here are a few things to consider as you develop your action plans and best practices for the offsite:
If you have people flying in from all over the region, country, or world, you need to consider travel solutions that minimize fatigue and expenses. Business travel is expensive, especially when you’re dealing with high-level executives who expect first-class travel and accommodations.
Will food be catered? Will it be provided by the venue? How far away are the bathrooms from your meeting locations? Where is the lodging — is it close to the venue?
Blazing-fast internet is non-negotiable unless the meeting’s purpose is to disconnect and focus. But prepare people for this in advance — going off-grid freaks some people out (like me, for example).
Is it a half-day, full-day, or multi-day event? Build in plenty of buffer time to let people settle in after travel, and plan some optional social events so your employees can choose between socializing or resting.
And, always keep in mind that not every moment needs to be filled! Give your employees some flex time to come up with their own ideas for activities (or a lack thereof — maybe they just want to kick back and relax, and that’s cool too!). If you schedule your retreat too rigidly, it will be anything but a welcome departure from daily life around the office.
Weigh the Opportunity Cost
An executive offsite is a major investment, both in actual dollars and in opportunity cost. While your tangible expenses include things like business travel and venue rentals, the opportunity cost is pulling your leadership team out of their regular work for full days, maybe more. That’s a serious ask.
So, make it count. Make sure your team walks away from the offsite with clear direction on strategic objectives. They should be aligned on action items and next steps, and they should have a sense of shared vision and renewed motivation. You might also want to schedule regular check-ins and/or a focused discussion at the executives’ next meeting to keep the momentum rolling.
If the opportunity or actual costs are too high, you could always consider a virtual offsite instead, which has its own pros and cons. On the positive side, there’s a massive cost savings on business travel, and people will spend less time away from the office. However, virtual offsites don’t provide the same bonding experience or collaborative fire as being in person, in the same room, face-to-face with your colleagues.
Invite the Right People
Who will be attending? The success of a strategy offsite depends heavily on who’s in the room. Ask yourself…
Who has the information and perspective we need to make informed decisions?
Who needs visibility or development opportunities?
Who will be offended if left out — and do you care?
Who will run the day-to-day operations while the team is out of pocket?
Often, the executive team and management team are the primary attendees. But, even if it’s not a full company offsite, consider inviting certain high-potential employees or key cross-functional figures. Just make sure your group size supports the meeting’s purpose — large groups might need more structure, whereas smaller groups can move faster and engage in more open discussion.
And, yes, if someone needs to pop in virtually for a key segment, it’s possible. But this can disrupt the tone and flow of the in-person experience. It’s best to get as many boots on the ground as possible to have a successful corporate retreat.
Set the Tone from the Start
The opening moments of any company offsite are crucial. They help establish your core message, the tone of the event, and employee engagement levels. Your kickoff should include a welcome message from a key leadership figure (i.e., CEO, founder, Chief of Staff), a high-level overview of the current state of the company, clear expectations and ground rules, and a walkthrough of the agenda.
This is also when to emphasize the stakes and the opportunity. No one is here just to fill time — they’re here to align around strategic initiatives, solve problems, hold important strategy meetings, and chart a course for the next year.
In addition, it doesn’t hurt if this opening message is delivered in an entertaining, inspirational, or otherwise memorable way. You want your employees to think they’re in for an engaging and worthwhile time, not checking their watches before the opening meeting is over. If you want to, you can bring in an outside presenter — like an inspirational speaker or entertainment figure — to give a more general fire-up speech that works in tandem with leadership’s more operational tone.
Carefully Craft the Main Sessions
No matter the specific goals, an offsite usually has a main session each day with the entire group. This is often an overview presentation, teeing up the current state of the org and getting everyone on the same page about the main themes you want to cover.
Then, your group can get into some participation exercises and back-and-forth exchanges. You can break people up into small groups, mixing it up to have people from different departments or functions working together. Try to get as many different combinations of people working and talking together throughout the offsite as you can.
Overall, the main sessions provide a lay of the land and the why driving the organization’s current objectives.
Use Exercises and Activities to Drive Participation
Don’t just talk at people. A great way to get buy-in is to involve the group through structured breakout sessions and hands-on exercises.
We had an offsite once where we wanted some of the team members to gel better post-merger. We had a DISC personality assessment facilitator run everyone’s reports beforehand and structured breakout sessions based on their DISC profiles. The resulting “a-ha!” moments transformed how team members interacted going forward.
For example, one person came up to me after discussing our DISC profiles and said that she now understood why I got so annoyed when she wrote me long emails. She thought she was being thorough and displaying her effort and research, when all I really wanted were bullet points.
Spend Time Just Hanging Out!
It’s important to never underestimate the power of simply being together as a group. Some of the best moments at successful offsites happen as a result of informal gatherings at the hotel or around town. You should also plan some shared experiences that are more than mere social events — they’re a vital part of team building, and they can create lasting connections that support collaboration long after the offsite ends.
I know a founder who rented a nice Airbnb for his team with an outdoor campfire. He had a “beers around the campfire” session in the evening where they casually discussed some of the fresh ideas they had just covered in the “formal” sessions earlier in the day. He found that people approached those conversations differently when they were in a new environment and casual clothes — hanging out in the backyard with drinks and s’mores — than they did in the meeting space.
Here are some team activities I’ve seen work well, depending on the demographics of your group:
Cooking and eating together are very bonding experiences.
Paint ‘n’ sip — there is really nothing quite like buzzed painting to bring a team together.
Top Golf or bowling can be fun for even the non-athletes on your team.
I’ve done outdoor rope climbs and mazes, which have their place for a younger group.
Notice how I didn’t mention escape rooms? Many people don’t actually like them, and they can be a real chore if you don’t want to be there.
Just make sure to build in enough time for rest. Introverts need space to recharge, and even the most enthusiastic participants appreciate downtime between sessions. If a session ends early, don’t stretch it — just let people go. You’ll get better engagement and boost morale when you respect their time and energy.
When Planning Your Next Offsite…
…think about these things! Your team members will thank you. To be honest, the difference between a great offsite and a lame one often comes down to putting in some extra effort on the little details. People like to feel valued and appreciated, especially when you’re asking them for days’ worth of their time and energy.
If you need help bouncing ideas around, let me know. I help a lot of Chiefs of Staff orchestrate these events for their leadership teams. I also know of some great event planners and event designers who create a holistic offsite experience. The right event designer can shape the tone, message, and ambiance — and maybe even emcee the function — while also nailing the logistics.
About The Author
Emily Sander is a C-suite executive turned leadership coach. Her corporate career spanned Fortune 500 companies and scrappy start-ups. She is an ICF-certified leadership coach and the author of two books, An Insider’s Perspective on the Chief of Staff and Hacking Executive Leadership.
Emily works with early to senior executives to step into effective leadership with one-on-one coaching. Go here to read her story from seasoned executive to knowledgeable coach.