12 Powerful Team Building Ideas for Your Next Retreat

Over the past years, we learned that we could accomplish almost every aspect of work remotely. However, team building virtually remains a challenge.

Building interpersonal connections is not easy to do online. Skift Research shows that 66 percent of corporate workers find it challenging to build connections with their colleagues virtually.

There’s one way that companies tackle this team building challenge – regular company off-sites or retreats. The Skift team were delighted to connect with colleagues in June at the company’s first retreat since the start of the Covid pandemic.

Buffer, Doist, and Atlassian leaders understood the importance of regular in-person gatherings for remote workers. As they created their blueprint for remote work long before the Covid pandemic, they trail-blazed the path for others who can learn from their approach to team building.

They have one thing in common: they put the team at the center of the event. 

We collected 12 proven team building ideas to help your team get to know each other, build relationships, and better work together.

📚 Structured Storytelling 

If your team has grown fast, you should create space for people to break down the barriers and talk to one another. This session supports those things through a process of structured storytelling. The core component is to have team members answer questions about their professional or personal life, including highs and lows. 

Here’s how to organize it:

1. Split the team into groups of 5 and explain the purpose of the exercise. 
2. Give the team 10min to write a story of their life, answering the following questions: 
   • What was the most memorable moment in your career/life?
   • What’s the most common misconception that others have about you?
   • What’s one thing that only a few people know about you?
3. Ask each person to narrate their story within their small group for about 10 min. The entire round will take roughly 50-60 min. 
4. Finally, bring everyone back and debrief with the whole group asking volunteers, “What is one interesting thing you learned from others?”.

👩‍👩‍👦‍👦 Team Sync: What Are You Working On?

In fast-growing teams, it’s easy to lose track of what other colleagues are working on. This can lead to misalignment and a general lack of focus. This exercise allows people to catch up on what others are working on and break silos once everyone gets back to the office. 

Here’s how to organize it:

1. Ahead of time, appoint two representatives for each team to share their team’s mission, key areas they’re responsible for, or major projects they’re working on. 
2. Create one roundtable per team (e.g. marketing, sales, product development, customer success, etc.) Tip: In case you’re hosting your retreat online, use breakout rooms. 
3. Let the rest of the team pick the roundtable to engage in a discussion with the representatives.
4. Host at least two rounds of 30 minutes so the coworkers can join at least two different teams. 

❓Turn Business Updates Into a Quiz

It’s unrealistic to expect that there won’t be any business presentations as part of the program. It’s not even a goal after all. Critical updates need to be communicated. But don’t present them slide by slide without turning to the audience. Make it a business quiz with high-value.

Here’s how to organize it:

1. Turn the business updates or key results into a quiz and let the team guess the correct answer to questions like: 
   • “How many new big deals did we close last year?”
   • “How many new features did we release?” 
   • “Which region was the fastest growing?”
2. Introduce the question and let the team vote.
3. Reveal the correct answers and provide additional business context.
4. At the end, announce winners with the most correct answers and give out prizes.

🪛 Screw Up Roundtables

We intuitively know that vulnerability tends to spark cooperation and trust. “Vulnerability doesn’t come after trust — it precedes it. Leaping into the unknown, when done alongside others, causes the solid ground of trust to materialize beneath our feet,” writes author Daniel Coyle in his TED article. This exercise helps the team to admit to their mistakes, demonstrate their vulnerability, and create an environment of trust.

Here’s how to organize it:

1. Split the team into groups of 5.
2. Give the team 3-5 min to think of the screw-up they want to share with others
3. Each person shares their mistakes within a small group for about 10 min each. The full exercise is about 60 min long.
4. Encourage others in the group to ask follow-up questions such as:
   • “What did you learn from it?”
   • “What would you do differently now?”.
5. Optionally, debrief the exercise with the whole group by “Who would like to volunteer and share their screw-up story?”.
6. Tip: It’s very powerful when leaders share their screw-ups publicly first. The rest will follow the led.

🧠 Brainstorming Qs for AMA

There are often big announcements at retreats such as when a CEO introduces a new strategy or new goals. It always creates tension – the team needs some time to digest the news. So give people a moment to reflect after a big announcement.

How to organize it:

1. Instruct the team to take 2-3 minutes and share their thoughts with the people sitting next to them.
2. Help them with a prompting question: “What are your thoughts on what you’ve just heard?”
3. After the discussions happen, encourage them to think of a question they want to ask the leaders.

🤼 Leadership Ask-Me-Anything

The previous activity naturally leads us to Ask-Me-Anything (AMA) sessions with leaders. It should be a permanent fixture on any off-site agenda. Dedicating space to questions is not only critical for clarifying any uncertainties, but it also helps to cement a culture of trust. 

How to organize it: 

1. If needed, get the buy-in from leaders on the idea of leadership Ask Me Anything session and brief them on how it works.
2. Allocate 30-45 min to the session and place it at the end of the business updates block in the off-site agenda.
3. Collect questions in advance or on the spot with Q&A tools so your leaders.
4. To ensure the most burning questions rise to the top, combine it with the previous exercise.

🍔 Social Lunch

Off-site lunches are typically the most social moments. Give people a little nudge to start a conversation with new colleagues with a list of questions. This exercise works great both in person as well as in online space over Zoom. 
How to organize it: 

1. Prepare a list of the icebreaker questions in advance.
   • What is the weirdest place you joined a remote call from?
   • If you were given an opportunity to take two years to learn a new skill, what would it be?
   • Which of your talents can you trace back to your childhood?
2. Distribute it to the tables or share a document with the remote people in case they stay connected over lunch at Zoom.
3. Before people leave for lunch, promote the exercise and encourage them to use questions for lunch conversations.

🧐 Newbies Quiz

More often than not, newbies find it awkward to introduce themselves. You can help them by running a Newbies Quiz that is based around the concept of “Two Truths One Lie”. We’ve learned some crazy stories about how our colleagues were escaping from a bear or erupting volcano. 

How to organize it:

1. Ahead of the off-site, collect two facts and one lie from your new coworkers.
2. During the meeting, put up a quiz question and encourage the rest of the team to spot a false statement.
3. Reveal the results on how the team voted.
4. Then get the introduced newbie to provide more details on what was true and what was false. 

🎬 Starter Kit and Talk Through It 

Another great idea by Redpoint Ventures and another cool way to make introduce new colleagues. Get people to create a visual starter kit about themselves. People can talk about where they’re from, what hobbies they’re into, and their past lives.

How to organize it:

1. Ahead of the off-site, ask new colleagues to come up with a starter kit which is a slide with images that represent them.
2. Images can include hobbies, visited places, favorite food, pets or anything else.
3. During the meeting, get them to walk the rest of the team through the pictures they put up on the slide. 

📊 Voting for the Most Valuable Feature

Off-sites are an ideal place to recap some of the biggest improvements on the product or outline the roadmap for the upcoming year. Treat it as an opportunity to get early feedback from the team. 

How to organize it:

1. Introduce some new product features.
2. Put up a multiple choice-poll and get the team to vote:
   • “What product feature do you think will be most valuable for our clients?”
3. If you happen to turn part of your off-site into a hackathon, you can introduce the projects one by one and ask the team what they think of every single one of them:
   • “How do you like this feature? [Rating 1-5]
   • “Any thoughts you’d like to share with the team?”

⚡️ Lighting Talks

The stage should be shared. Let the coworkers seize it and talk about what they’re most passionate about. I’ve seen some introverts on the team deliver incredible presentations on free diving, the latest advancements in near-orbit satellites or an impromptu stand-up comedy. It’s a simple but super-powerful format for people to reveal more about their lives.

How to organize it:

1. Gather volunteering presenters ahead of the off-site.
2. Brief them to prepare short short talks of 10-15 min on the topics they’re most passionate about.
3. During the off-site, host this session in the evening, after the official program is over.
4. Have a moderator who will steer the flow and watch the time.

🎵 Name That Tune

Off-sites are a place where the company culture fully comes into life. And nothing brings people together more than music. You can organize your version of the TV Show from the 50s “Name That Tune”. This is another cool idea from Redpoint Ventures.

How to organize it:

1. Pick 3 contestants from your coworkers.
2. Give them buzzers (the fastest gets the chance to answer first).
3. Let them guess the songs and tunes they’ve just listened to.
4. Run 7-10 rounds and announce winners at the end.

The success of a team retreat ultimately depends on the willingness of the team members to get to know each other, build relationships, and collaborate. By using some of these activities, you can create an environment where everyone feels comfortable and can work together to make the most of the retreat.