​​Making Every Moment Count: How to Plan a Company Retreat

Planning, organizing, and hosting a successful corporate retreat can be exciting and overwhelming.

In this blog post, I walk through the entire process of organizing a corporate retreat and some valuable tips to make the journey smoother.

Identifying your goals

Corporate retreats offer a fantastic opportunity to align on your company's mission, celebrate employee successes, and strengthen your company culture, all while fostering team bonding.

Here are some common goals a retreat can help achieve.

Goal 1: To celebrate achievements

First and foremost, a company retreat is an opportunity to celebrate your team’s accomplishments. Take the time to reflect on the milestones your team has achieved and acknowledge every individual's hard work and dedication. It's a chance to express gratitude.

Goal 2: To reward everyone for their hard work

A retreat is ideal for rewarding your team for their outstanding efforts. Plan activities and surprises that show how much you value their contributions. This gesture will foster a sense of pride and motivate them to continue giving their best.

Goal 3: To build your company culture

Company retreats are excellent opportunities to reinforce and strengthen your company culture. Choose activities that embody your organization's values and promote teamwork. Consider workshops or sessions focusing on personal growth, team dynamics, and skill development. By nurturing your company culture, you'll create a strong unity and identity among your team members.

Goal 4: To create opportunities to connect

A retreat provides a unique chance for team members to connect personally and forge deeper relationships, especially if they’re working remotely. Plan interactive activities that encourage collaboration and create opportunities for meaningful conversations. From team-building exercises to shared meals, these experiences will foster trust, camaraderie, and understanding.

Goal 5: To strategize the work ahead

Use the retreat to align your team on upcoming priorities. Set aside dedicated time to discuss goals, objectives, and action plans. Encourage open dialogue and collaboration among team members. By involving everyone in the decision-making process, you'll foster a sense of ownership and collective responsibility. This step ensures everyone is on the same page, working towards a shared vision.

Your retreat planning action plan

Now that we have outlined the core goals for a retreat let's delve into the essential steps to plan a company retreat that brings these to life.

Step 1: Define the purpose and objectives

Identify the specific goals and outcomes you want to achieve through the retreat. Communicate these to your team early and often, emphasizing the importance of their active participation.

Tip: Remember your retreat goals. Getting lost in all the logistics involved in planning a retreat is easy. That’s why it's crucial to consider measurable and identifiable goals you aim to achieve by the end of the retreat. By establishing primary objectives early on, you'll lay the foundation for effective planning across various aspects of the retreat.

Step 2: Choose the right location

Select a destination that aligns with your company's values and the desired retreat atmosphere. Consider factors such as accessibility, on-site dining, and the availability of engaging activities.

Tip: Go remote. Of course, you want to factor in where most of your team members live, where your office(s) may be located, and ease of access— however, control’s most vital for me when deciding on a retreat location. If your team stays together at a resort or remote location, it gives people the freedom to have fun within the same space. But if you’re located in a city or urban environment, your team will likely want to get out and explore, making it hard to control the logistics of your retreat.

Tip: Find a partner. Does your venue have an events manager you can work with? Or are you only talking to people in sales? When deciding on the right location, consider what type of internal support the venue can provide. An events manager who can bring value when planning your activities is a game changer.

Step 3: Create a budget

When planning a company retreat, the cost can vary significantly based on the number of attendees, location, time of year, and agenda. Your budget should cover expenses like recreational activities, food, and accommodations.

Strive for a realistic budget while keeping a decent buffer for unexpected expenses that may arise (i.e. weather delays, missed flights).

Tip: Private accommodations only. One important consideration is the accommodation arrangements, specifically whether team members will have the option of individual rooms or they’ll be in shared accommodations. Here’s the thing - no one wants to share a room. Don’t lie to yourself and think otherwise. So budget your retreat accordingly. If this means scaling back on other ideas, it’s worth it in the long run.

Tip: Focus on food, not drink. Food is what will fuel a successful event. So one way to reduce your spending is not to cover the cost of alcohol. Consider whether each dinner needs to have alcohol. You could offer table wine on the first or last night of the retreat as a way to celebrate. For the rest of the time at the retreat, team members can be responsible for paying for their drinks.

Step 4: Design an engaging agenda

Create a well-structured agenda that balances work sessions, team-building activities, and free time. Ensure that each element aligns with your goals.

Tip: Schedule downtime. Each day needs to have scheduled downtime. We want to spend lots of time with our team members during the retreat, but not every minute. Give people space to refresh and recharge.

Tip: Provide gift cards. You’ll never be able to capture the interests of all your team members. So give them gift cards to the retreat location or nearby areas so they can explore some of their interests on their own time.

Step 5: Get everyone involved

Encourage participation and ownership by involving team members in the retreat planning process. Allow them to contribute ideas, suggest activities, and take on responsibilities. This inclusivity will foster a sense of investment and excitement.

Tip: Establish a retreat committee. You’re leveraging this committee to help plan smaller items - what swag to get, putting together a retreat playlist, meeting people at the airport, grabbing snacks for bus rides, etc. The team is always super keen to help with any surprises and delights.

Step 6: Pay attention to the logistics and details

Take care of all the logistical aspects, including transportation, accommodation, meals, and necessary equipment. Pay attention to dietary preferences and requirements to ensure everyone feels comfortable and catered to.

Tip: Give yourself time. Planning a retreat is a long process - you’ll need somewhere between 3-6 months to get it right. It also requires your full attention, so prioritize it alongside your other ongoing commitments. There may be some items you delay working on as a result.

Tip: Decide on devices. Do your team members need to bring their laptops? How much will they use them? Is it easier to just pack stationery for group activities? Decide whether or not team members need their devices to participate in team-building activities.

Tip: Send out your “Save-the-Date” early. We want to ensure as many people as possible can participate in the retreat, so giving advance notice is crucial. If someone can’t attend the retreat, think about how you will help them participate before, during and after.

Tip: Have team members book their flights. Avoid the logistical nightmare that can be flying. When team members book their flights, they’ll take ownership of managing any delays, etc.

Tip: Write a company-wide “Out-of-Office” message. Drafting a template will help your employees get ready for their time away.

Tip: Create shared communications channels. For instance, create a retreat-specific Slack channel where team members can ask questions. And have a dedicated section of your intranet that outlines the daily agenda, FAQs, and other essential information.

Tip: Talk about the agenda a lot. Even if the plan is online, your team will still ask you about what’s happening daily. So start each day and each activity with a reminder of the day’s agenda.

Step 7: Make it memorable

Add special touches and surprises that create lasting memories. Whether it's a themed dinner, a surprise guest speaker, or a fun team-building challenge, these experiences will make the retreat unforgettable.

Tip: Look for outside support. Some facilitators specialize in organizing group activities. Use them. Having someone outside your organization run an activity helps all team members participate equally.

Tip: Get some retreat-specific swag. What’s something unique about the location? The time of year? For example, I planned a retreat at a ski resort, so all our team members received a company-branded toque.

Tip: Assign someone to take photos. Identify team members each day who’ll be responsible for taking pictures. It’s easy to forget to capture moments, so get the team to help.

Step 8: Follow up and implement action plans

After the retreat, ensure that the ideas and decisions generated during the event are followed through. Implement action plans, track progress, and provide ongoing support to ensure that the retreat's outcomes have a lasting impact.

Tip: Send out a post-retreat survey. As with anything, we want to hear from team members directly. What did they think of the retreat location? The accommodations? The activity? Also, ask them about their most memorable experiences and what they’d like to see in future retreats.

Remember, a successful company retreat creates an environment where your team feels appreciated, inspired, and connected. By setting clear goals, planning engaging activities, and fostering a supportive culture, you'll create a retreat that achieves multiple objectives and leaves a lasting positive impact on your organization.

Happy planning!

Yiorgos Boudouris