How to Plan a Company Retreat That Builds Genuine Team Connections

By Duncan MacNally

A company retreat can be much more than a change of scenery, a few group activities, and a dinner at the end of the day. When planned thoughtfully, it can give employees the time and space to build relationships, communicate more openly, understand different working styles, and return to work with a stronger sense of connection.

However, genuine team connection does not happen simply because employees are placed in the same location. A retreat filled with forced games, back-to-back presentations, or overly structured activities can have the opposite effect. The goal should be to create an environment where employees naturally interact, collaborate, and get to know one another beyond their usual job responsibilities.

This matters because workplace connection remains closely tied to employee engagement. Gallup's latest research reports that global employee engagement fell to 20% in 2025, its lowest level since 2020. Gallup also notes that engagement is closely associated with productivity, profitability, retention, and other business outcomes.

So, how can companies design a retreat that employees genuinely value?

Start With a Clear Purpose

Before choosing a destination or booking activities, determine what the retreat is supposed to accomplish.

Is the primary goal to help a newly formed team get acquainted? Is the company trying to improve collaboration between departments? Perhaps employees have been working remotely and need opportunities to reconnect in person. A leadership team might also use a retreat to strengthen communication and establish priorities for the next year.

Having a clear purpose makes it easier to decide what belongs on the itinerary and what does not.

For example, if relationship-building is the priority, spending six hours in conference rooms listening to presentations probably isn't the best approach. Instead, the schedule could combine a short strategic session with informal meals, collaborative activities, and unstructured social time.

The retreat should feel intentional without feeling like another workday.

Choose a Setting That Encourages Interaction

Location plays a surprisingly important role in how people interact.

A destination that provides comfortable shared spaces, outdoor areas, dining options, and recreational opportunities gives employees more reasons to interact naturally. A resort, countryside property, beach destination, or city with accessible attractions can all work, depending on the company and its budget.

Consider the practical needs of employees as well. Travel time, accessibility, accommodation quality, dietary requirements, weather, and transportation should all be considered before finalizing the location.

The ideal setting should remove unnecessary logistical stress rather than create more of it.

It is also worth avoiding a venue that separates employees too much. If everyone disappears into individual rooms immediately after dinner, the retreat loses some of its social potential. Shared lounges, outdoor areas, communal dining spaces, and casual gathering points can encourage spontaneous conversations.

Build the Schedule Around Conversation, Not Constant Activity

One of the biggest mistakes companies make is trying to fill every minute.

A retreat does not need an activity at 9:00, 10:00, 11:00, and 12:00 simply because those spaces are available. People need breathing room.

Instead, create a rhythm that alternates between structured and unstructured time. A morning workshop could be followed by lunch and free time. An afternoon team activity could lead into a casual dinner. The next morning might begin with a short reflection session rather than another lengthy presentation.

Unstructured time is particularly valuable because some of the most meaningful conversations happen when employees are not being instructed to interact.

Someone may discover that a colleague shares the same hobby. A manager might learn more about an employee's interests. Two people from different departments may realize they have been solving similar problems.

These seemingly small interactions can strengthen relationships over time.

Select Activities That Encourage Collaboration

The best retreat activities are not necessarily the most expensive or elaborate ones. They are activities that give employees something to do together without making the interaction feel artificial.

Consider activities such as:

• Cooking workshops
• Outdoor challenges
• Creative classes
• Escape rooms
• Group hikes
• Volunteer projects
• Casual sports
• Trivia competitions
• Scavenger hunts
• Team-based problem-solving activities

The important thing is to provide different types of experiences.

Not everyone enjoys competitive activities. Some employees may prefer creative experiences, while others feel more comfortable participating in relaxed social settings. Giving people choices can make the retreat more inclusive.

For a sports-oriented company, for example, a tennis master class could offer a fun way for employees to learn something together while creating opportunities for conversation and friendly competition.

The activity itself is only part of the equation. What matters most is whether it creates a natural reason for people to interact.

Mix Departments and Familiar Groups

Employees naturally gravitate toward people they already know. While there is nothing wrong with that, a retreat can be an opportunity to expand relationships beyond established circles.

If every activity allows employees to choose their own groups, colleagues from the same department may stay together throughout the entire retreat.

Instead, occasionally create mixed groups.

A marketing employee might work with someone from finance and another person from operations. A senior employee could be paired with a newer team member during a collaborative challenge.

This does not mean forcing employees into uncomfortable situations. The objective is simply to create opportunities for cross-functional conversations that may not happen during normal working hours.

Over time, these connections can make collaboration easier because employees have a personal point of reference when they need help from another department.

Make Meals a Central Part of the Experience

Food is one of the easiest ways to create informal connection.

Rather than treating meals as simple breaks between activities, make them part of the retreat experience. Shared breakfasts, long lunches, outdoor dinners, or casual food stations can encourage employees to spend time together without a formal agenda.

Seating arrangements can also make a difference. Instead of assigning employees to sit with their closest colleagues every time, consider mixing groups across different meals.

For evening events, the atmosphere matters just as much as the menu. Comfortable seating, appropriate music, good service, and an environment where people can actually hear one another can encourage longer conversations.

If alcohol is part of the event, companies should also provide appealing non-alcoholic options and ensure responsible service. Professional event staffing can help organizers maintain a welcoming environment without making the evening feel overly formal. For larger gatherings, working with corporate event bartenders can also help streamline beverage service while allowing organizers to focus on their guests.

Give Employees Some Choice

A retreat becomes more engaging when employees have some control over how they spend their time.

Instead of creating one mandatory activity for everyone, consider offering several options.

For example, an afternoon could include:

• A guided outdoor activity
• A wellness session
• A recreational sport
• A creative workshop
• Free time for informal socializing

Employees can choose what suits their personality and energy level.

This approach is particularly helpful for introverted employees or people who may not enjoy highly competitive team-building exercises. Genuine connection does not require everyone to participate in exactly the same way.

The goal is to create opportunities for connection, not to measure participation.

Create Opportunities for Honest Conversation

A retreat can also provide space for conversations that are difficult to have during a normal workday.

Consider incorporating short discussion sessions around questions such as:

• What helps you do your best work?
• What is one thing another team does that you appreciate?
• What is one process that could be improved?
• What is something you would like your colleagues to understand about your role?
• What would make collaboration easier?

These conversations should be handled carefully. Employees need to feel that their responses will not be used against them.

Leadership should listen rather than immediately defend existing policies or explain why suggestions cannot be implemented.

When employees see that their perspectives are genuinely valued, the retreat can become more than a social event. It can contribute to a healthier workplace culture.

Don't Make Leadership the Center of Everything

Executives and managers naturally play an important role in company retreats, but the event should not feel like an extended leadership conference.

If senior leaders dominate every conversation, employees may hesitate to relax or speak openly.

Give employees opportunities to interact with leadership informally. A casual breakfast table, shared activity, or small-group discussion can often create better connections than a formal presentation.

Leaders should also participate rather than simply observe. Joining an activity, sharing a meal, or telling a personal story can make them feel more approachable.

This is especially important because managers have a major influence on employee engagement. Gallup's 2026 workplace research reports that manager engagement declined significantly in 2025, with managers accounting for a substantial portion of the recent global decline in engagement.

Offsites Are Becoming More Social

Recent research supports the shift toward more relationship-focused company retreats. Emburse's 2025 State of Corporate Offsites report, based on a survey of 2,000 U.S. full-time employees, found that 59% of companies reported increasing their offsite budgets since 2019, while organizations averaged 2.6 offsite events annually. The report also found that companies were dedicating 44% of event time to social programming and team building.

This suggests that companies are increasingly treating offsites as opportunities for connection rather than simply locations for meetings.

Design for Different Personalities

A successful retreat should not reward only the loudest or most outgoing employees.

Some people thrive in large group settings. Others connect more easily through one-on-one conversations or small groups.

Build variety into the itinerary.

A large group dinner could be followed by smaller discussion groups. A competitive activity could be balanced with a relaxed workshop. A presentation could be followed by free time.

This gives employees multiple ways to participate.

Even simple details can help. Avoid requiring everyone to speak publicly unless necessary. Make participation in recreational activities voluntary. Give employees access to quiet spaces when they need a break.

Inclusivity is not about making everyone behave the same way. It is about creating an environment where different personalities can participate comfortably.

Leave Room for Spontaneity

Some of the best retreat memories cannot be planned.

A group may decide to grab coffee together after breakfast. Employees might start playing a casual game after dinner. A few colleagues may continue a conversation long after a workshop ends.

Do not schedule these moments out of existence.

A little flexibility allows employees to follow their interests and form relationships naturally. The retreat should have enough structure to provide direction but enough freedom for genuine interaction to develop.

Follow Up After the Retreat

The retreat should not end when everyone gets home.

Without follow-up, the relationships and ideas developed during the event can quickly disappear once employees return to their normal routines.

A week or two after the retreat, ask employees what they enjoyed, what they found valuable, and what could be improved.

More importantly, identify ideas that should be carried into everyday work.

If employees discussed improving communication between departments, create a process for doing so. If a team identified a recurring problem, assign someone to address it. If employees enjoyed a particular social activity, consider incorporating similar experiences into future events.

The purpose of follow-up is to turn a temporary experience into a lasting change.

Measure Connection, Not Just Attendance

Traditional event metrics such as attendance, spending, and satisfaction scores are useful, but they do not tell the entire story.

Consider measuring whether the retreat actually improved relationships.

A simple post-event survey could ask:

• Did you meet colleagues you had not previously worked with?
• Do you feel more comfortable approaching people from other departments?
• Did the retreat help you better understand your colleagues?
• Did you feel included in the activities?
• Would you participate in a similar event again?

You can compare these responses with future engagement surveys to identify whether the retreat is contributing to broader workplace improvements.

Make the Retreat Feel Human

Ultimately, a successful company retreat is not about having the most impressive destination or the longest list of activities.

It is about giving people a reason to put their usual work roles aside for a moment and connect as human beings.

The strongest retreats combine purposeful conversations with relaxed social experiences. They give employees opportunities to collaborate, laugh, learn, eat together, and discover shared interests. They also respect different personalities and avoid turning every interaction into a mandatory team-building exercise.

When employees return to work knowing more about the people around them, communication can become easier and collaboration can feel more natural.

That is the real measure of a successful retreat: not how packed the itinerary was, but whether employees leave feeling more connected than when they arrived.

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