How to Host a Digital Retreat Your Team Will Love
With real-life examples from Hummingbird Marketing Services’ Digital Retreat
By Andi Lucas, Founder & CEO, and Elizabeth Phillips, Marketing Manager, Web & Graphic Design
Edited by Sarah Fils-Aime, Marketing Content Specialist
The workplace in the digital age has shifted dramatically, with more and more team members reporting remotely. With advancing technology, it’s become easier than ever to work from anywhere at any time. From the home office to the neighborhood coffee shop and everywhere in between, it’s undeniable that remote work has changed “office space” as we know it. With remote opportunities growing, we find a welcomed shift toward a better work-life balance — but does this freedom mean we must sacrifice team alignment?
With most or all team members working from home, potentially across state lines or several time zones apart, it can seem difficult to connect. But with a little extra effort and creativity, a remote team can be full of camaraderie and synergy.
At Humminbird Marketing Services, we pride ourselves on our connected, collaborative, fully remote team! Through intentional planning, we all stay on the same page and bond, even remotely. We want to share with you one powerful way we connect — allow us to introduce you to the Digital Retreat. Based on the principles of a traditional, in-person retreat, a digital retreat allows members to participate without the limitations and budget of bringing everyone to the same location.
Who said remote teams can’t be completely in sync? At Hummingbird Marketing Services, our 100% remote team stays connected through team bonding and digital retreats.
Whether your team needs a chance to reconnect or you’re looking for ways to maintain and nurture a collaborative environment, planning a digital retreat creates an opportunity for team bonding, growth activities, and an energizing morale boost. Keep reading for our detailed step-by-step guide on how to host a digital retreat, along with the tips and tricks we discovered from our highly successful, fully-remote retreat.
Use these quick links to jump to the main topics discussed in this article.
Step 1: Set a Date for Your Digital Retreat
Planning the ideal time for your digital retreat will determine your success. This might seem like an obvious first step, but intentional and thoughtful planning is important. Many factors are worth considering when selecting a time.
Follow these tips to help you choose the best schedule for your digital retreat:
Optimize the slow season.
If your industry naturally has a lull in business a certain month, quarter, or time of the year, plan your digital retreat around this season. This will ensure your team isn’t being pulled from important deadlines and can give an energetic boost before gearing up for a busy quarter. You should also consider which days of the week are more or less busy when selecting dates for your digital retreat.
Choose a significant time of the year.
Consider if your business has a certain date or time of the year that is monumental or worth celebrating. With a little thoughtful brainstorming, the best date may become obvious. For example, a large milestone or business anniversary could be a wonderful time to celebrate and realign with a digital retreat.
You also might consider seasonal significance in your planning. We chose to schedule our digital retreat at the end of Q3, at the very start of fall. The autumn season represents change and preparing for the next year, which was the focus of our retreat. The leaves changing colors and the shifting temperatures provided the perfect backdrop for a mindset of change.
If summer is slow for your business, plan a summertime digital retreat with a focus on sunshine, brighter days, and gearing up for a busy fall season!
How long should a digital retreat be?
The length of your digital retreat will differ based on what makes sense for your business, goals, and itinerary. Your retreat should be at least a full day, and typically, a week is the longest it should be. Your digital retreat should be long enough to include all planned activities without feeling rushed. Consider the need for breaks, and remember, your team will appreciate extra time to bond and truly enjoy each other’s company. Be realistic about the amount of time you need to achieve the goals of your retreat.
Step 2: Set Digital Retreat Goals
Don’t go into your digital retreat without setting some goals. You’ll want a clear concept of what you want to achieve from your retreat so that your agenda is built with intention. Your goals could be as simple as team bonding or a more complex strategy that is aligned with specific upcoming company milestones.
What are some examples of goals for a digital retreat?
If you’re planning a new product or service launch, you may want to dedicate time in your retreat to brainstorming sessions. Maybe you’re experiencing a change in leadership — set up an open discussion on improving processes. If your team has recently grown, your focus might be on cultivating a collaborative and tight-knit culture. Ideally, you’d set at least two goals: one that directly focuses on improving your company’s success, and one that centers on your team bonding and alignment.
Goals can be highly specific or incredibly broad, and brainstorming within the digital retreat can help you reach more specific goals for your brand for the future. Setting more than one goal ensures a robust and proactive agenda, but be careful not to over-achieve and overwhelm your schedule. Setting too many goals can lead to a confusing and unorganized agenda. In short, set goals for your retreat that align with your company’s long-term goals.
Brainstorming sessions are just as effective virtually! Consider hosting a brief team meeting to brainstorm goals for your retreat to ensure that final decisions reflect your group’s aspirations.
Setting goals for our digital retreat led to long-term success.
For our digital retreat, we set a broad goal of team bonding, alignment, and establishing a growth mindset for our future. Taking these broad goals, we were able to set more specific goals, which helped our agenda creation process.
A major goal was to redefine our company values. By defining who we are, we were also able to realign with our target audience. We established what work we valued most and what was leaving us feeling burnt out. This allowed us to hone in on the services we do best (aka our Zone of Excellence). We also dedicated time in our digital retreat to brainstorm business growth ideas for the upcoming year. We created a safe space for our team to be honest with one another and share ideas, which, in turn, optimized our communication, allowed us to develop a strategy for the new year, and improved the services we offer.
Step 3: Pick a Theme for Your Digital Retreat
Themes create cohesion throughout the digital retreat and can help clarify goals and company values. Plus, themes are fun and exciting, creating hype for your virtual event. Although it’s not absolutely necessary, having a theme can help keep everyone on the same page and drive elements of agenda items and team-building activities.
How do I pick a theme for a digital retreat?
Themes can be inspired by your industry, your retreat goals, or the time of year. A stand-out theme will also tie in elements of your brand. Brainstorm themes that reflect your industry and consider options that match your goals for the next quarter or year.
If you think of a more generic theme or overarching concept, use that as a foundation for creating a clever theme that matches your brand. For example, we chose the theme “Ready to Soar,” which references our branding as Hummingbirds, but also established our goal to prepare for a busy holiday season and the upcoming New Year.
A clever digital retreat theme will align with your branding. Because we’re Hummingbirds, we settled on “Ready to Soar.” Some honorable mentions from our theme brainstorming: Taking Flight, Soar to New Heights, and Ready for Takeoff.
Consider each individual on a team.
In order to plan a digital retreat that is effective, you’ll want to be thoughtful of your audience. Consider the professional goals each individual on your team may have, while also keeping in mind their personal goals and interests. A fantastic virtual retreat will appeal to your team on a personal level. You want your people to be excited about this! Consider holding a brief brainstorming session with your team to hear ideas and feedback on what activities and sessions are intriguing to your team. Then, use this information to establish a theme and plan events.
Once we picked our theme we had fun incorporating it into the rest of our retreat, including these inspirational quotes we added to our meeting agenda.
What are some examples of digital retreat themes?
Wellness, Sustainability, and Work-Life Balance Themes
A wellness theme is a great general idea for a digital retreat that is focused on promoting work-life balance as well as company wellness. Sure, this theme is an easy tie-in for any business in the wellness industry, but it is just as relevant to any other company — wellness is a unifying practice. You can tie the wellness theme into your industry or the time of year, for example, “Winter Wellness Retreat.” Consider getting more specific with this theme, for example, “Work from Home Wellness,” where topics focus on work-life balance for remote workers.
Adding a virtual yoga or meditation session to the agenda can break up meetings, bond team members, and promote a healthy lifestyle. This is an especially great idea for wellness-themed retreats.
Decade-Inspired Theme
If your business is more than a decade old, consider a theme focused on looking back. Sometimes the best way to move forward is by learning from our past. Plan a digital retreat around a significant anniversary, and consider a theme that honors your brand’s origin. For example, a ’90s-themed 30th anniversary digital retreat. Have fun with some ’90s trivia while also revisiting company values, reflecting on the past three decades, and brainstorming for the future.
It may be more fitting to choose a general theme, such as “Retro Revival,” with the same focus on looking back, reflecting on the past, and realigning with values, all with the fun of retro elements and activities. On the opposite note, consider a futuristic theme that focuses on goal setting and growth for the coming years.
Themes Focused on Growth
If your primary goal for a digital retreat is expansion, increased revenue, and overall encouraging a dramatic growth, create a theme that reflects that mission. Visit the mountains without ever leaving your desk with a “Reaching New Heights” theme that plays on mountain imagery and encourages taking leaps and risks to level up.
For a bookish crowd, you may consider a “Next Chapter” theme that focuses on writing your brand’s next chapter. Any growth-focused theme can apply to company-wide growth as well as individual growth, and you’ll want to include elements that focus on both personal and professional development in your planning.
Themes Centered on Communication, Collaboration, and Team Building
Collaboration and communication are key elements to a successful remote team. A theme centered on these aspects can be great for any virtual team, especially if your goals are team bonding or better communication. Consider a “Speak-Up” theme that creates or reinforces a speak-up culture where idea sharing is encouraged and everyone feels safe sharing their opinions. Activities can focus on team bonding and brainstorming sessions. Consider adding sessions about creating a safe space in the workplace or how to be a better listener to your agenda.
Step 4: Make an Agenda
Now that you have your dates secured, goals set, and theme established, you are ready to create an agenda for your digital retreat! This is the fun part where all the pieces fall into place and the real planning takes action.
Include agenda items that are inspired by goals.
Make sure that for each goal you set, there is at least one, if not a few, agenda items that focus on that goal. Make time to accomplish company goals, while also organizing at least one activity that can help individuals work toward personal development.
Everything starts with a dream. Don’t be afraid to dream big when setting goals for your retreat.
Virtual Retreat Session Ideas
You don’t want to host a retreat that consists primarily of one person leading discussions and presentations. Instead, consider asking company leaders as well as other team members to lead a session on a topic that interests and inspires them. This will create variety in your agenda and allow individuals to share their strengths and expertise.
As a small team, we were able to let each team member lead a session during our digital retreat, which made each of us equally invested in the retreat and eager to learn from one another.
Consider scheduling at least one session that is led by someone outside of the company. From fun team-bonding activities to virtual classes led by experts, the sky is truly the limit! A mental health session would be great for promoting work-life balance and wellness in the workplace. A class focused on continued education in your field would be invaluable for your team and business. We chose to kick off our retreat with a presentation led by business coach Dave Erland, which got us geared up for the rest of our retreat!
A Simple, but Powerful Agenda Item: The 16 Squares Activity
This activity is great for setting both personal and professional goals, and all you’ll need is a pen and a piece of paper!
Fold a piece of paper in half four times until you have a small folded square. Unfold the paper, and you should have created 16 squares within the single sheet of paper.
In each square, write down one thing you want within the next year. This can be a professional accomplishment, a personal dream, or a plan for the future.
Date your paper and then fold it back up and tuck it away in a safe, but memorable, space. In one year (maybe during your team’s next digital retreat?), you can revisit your 16 squares to discover what you accomplished. The idea is simple — even just writing something down, speaks your goals and dreams into existence and propels you toward fulfilling them.
Make time for team bonding.
Even if team bonding is not a major goal, make sure to include some fun icebreakers and engaging exercises. Team building should always be a priority, and a digital retreat is the perfect time for your team to come together. Consider ending each day with an event that is not centered on work tasks, but instead on getting to know one another outside of work communications. Explore online games and virtual escape rooms, take a virtual cooking class, or purchase materials to do a craft together on a video call. Your team bonding can be as simple as a virtual happy hour while still being incredibly effective and plenty of fun!
Our team celebrated the end of our retreat with a digital happy hour. Everyone grabbed their favorite beverage and we spent an hour talking, laughing, and growing closer as a team.
Take Time to Celebrate Your Team
Dedicate some time during your retreat to applaud your team and any achievements from the past year. You can honor outstanding individuals with a simple shout-out or consider hosting a virtual awards ceremony to award individual and team accomplishments.
Don’t forget about breaks!
Just as you would with an in-person retreat, make sure to include plenty of time for meal times, bio breaks, and to simply break up the day into digestible chunks. You don’t want participants to get Zoom fatigue or overwhelmed with information. Breaks can help keep people’s attention focused while allowing time to consider all the new information.
Don’t trap yourself into an 8-hour workday; instead, build a schedule that makes sense for your team and goals. Oftentimes, a shorter day, packed with intentional activities and timely breaks, can be more effective and productive than a forced 8+ hour day where participants lose interest or get meeting fatigue.
Breaks can also be scheduled as time to work on an activity before your team regroups. For example, we scheduled a 90-minute lunch break for the first day of our retreat and used the extra time to work on a personal goal-setting activity.
A simple, but fun creativity-building exercise we did involved printing out sheets of paper with random doodles or lines on them. We each received the same document and drew whatever we wanted around the doodles, without seeing each other’s work.
After we each finished our drawings, we showed them to each other on our video call. This exercise is a fun demonstration of our vast differences in perspectives and creative thought processes!
Step 5: Sprinkle in Some Fun
Who says a business retreat has to be boring? If you follow the above steps, you’re guaranteed to launch an effective digital retreat, but to create a virtual retreat experience that leaves a lasting impression, be sure to include some fun surprises. If you create a memorable digital retreat, your team will look forward to it every year, keeping morale and excitement about company goals at an all-time high.
Our favorite way to incorporate surprises into our digital retreat is with The Days of Gifts, a company that hand-selects and wraps small gifts, creating a bundle of gifts where one can be unwrapped each day. We each received a 7-day bundle and opened the gifts throughout our 2-day digital retreat. We unwrapped the surprises together as a group, with four small gifts opened throughout the first day of our retreat and three gifts unwrapped on the second day.
Whether you go with thoughtful gifts, a surprise speaker, or a mystery team-bonding activity, a fun surprise will keep participants excited and ensure you plan a memorable virtual retreat!
Our team each received a 7 Days of Gifts bundle, which was a fun surprise, as we unwrapped presents throughout our retreat.
Between goal brainstorming sessions, educational presentations, fun team-bonding activities, and lots of laughter, our team hosted a memorable digital retreat that left us feeling closer than ever and excited for our company’s future!
Step 6: Make it a Priority
Last, but certainly not least, make sure your digital retreat is a priority — not just for your team, but for yourself as a leader and your company. Close your business for the day or days that your retreat is scheduled so your team can fully focus on bonding, brainstorming, and goal setting. Make sure clients know you won’t be available, and resist the urge to check emails and other alerts.
Eliminating distractions will allow you to be fully invested and present, ensuring the best outcome from your retreat. Remember, your digital retreat is only one day, or one week, out of an entire year. By making the most of this small amount of time, you will reap the benefits for months or even years. This is an investment that future you will be grateful you made.
So what are you waiting for? Start taking the steps to plan your digital retreat today!
