Top Icebreakers To Build Trust And Intimacy At Your Next Offsite

In this post, we'll cover 3 of our favorite icebreakers including: "Curated Conversations", "TEDx Style Talks", and "Life Walks"

Every full day at your offsites should start with icebreakers.

They are one of the best ways to quickly build trust and intimacy among your attendees, give people a “warm up” before diving into important work for the day, and foster a more positive, empathetic and high-candor tone for the following sessions.

But, the issue with most icebreakers is that…they suck.

So that you can lead the charge at your next offsite, and give your team the icebreakers they deserve, here are a few of our favorites (along with facilitator notes you can follow yourself or share with your team leaders).

(Below, we’re covering only 3 icebreakers for the sake of time, but if you plan your next team retreat with Offsite, we can offer many other session ideas and agenda structures based on your business objectives. We can also connect you to expert keynote speakers and facilitators. Head to offsite.com to learn more!)

Curated Conversations

As the founder/CEO of Offsite, I lead our team through Curated Conversations at almost every offsite we host. We also do a quick version of this during our weekly All-Hands on Zoom, in a “question of the day” format with 5 minutes for randomized breakouts.

As the facilitator, you will share a question prompt with the entire room, then ask attendees to break into random groups of 2 to discuss their answers to such prompts.

At an offsite, you can play with how long this exercise lasts, and how many round of questions you’d like to offer. I recommend either 30-60 minutes for this icebreaker, with five rounds of curated conversations, lasting either five or ten minutes each round depending on how long you’d like to do icebreakers for.

Each round should come with a new conversation prompt. As the facilitator, you should also encourage everyone find new partners for each round.

Conversation prompts can be personal or professional in nature, depending on what kind of connections you are hoping people will make at your offsites. I like giving people personal prompts on the first full day of an offsite and professional prompts related to the business on the second or third day of an offsite.

Sample prompts include:

• “What are you grateful for?”

• “Tell me what a ‘Day In The Life’ looks like for you.” 

• “What experiences or accomplishments in the past year are you most proud of?”

• “What did you want to be when you grew up?”

• “What did you do before working at [our company]?”, 

• “Where do you see yourself in 10 years?,

• “What are some of your highlights or best moments from working at [our company] thus far?” 

TEDx Style Talks

This ay require some “pre work” from your team, or you can invite people to share their TEDx style talks on-the-spot.

Either way, invite as many people as possible to share a 5-10 minute presentation on something they are passionate about outside of work.

This provides the team with an opportunity to learn more about one another and sets the tone for an engaging offsite where everyone will be expected to participate throughout the week.

Hopefully, your colleagues walk away with greater connection to the causes, hobbies, and passions each other have outside of work.

(For extra laughs, you can send the following video to your team in preparation for the offsite, as they’re developing any slides to go along with their talk).

Life Walks

Life walks are a more serious icebreaker that should lead to increased empathy and connection among your team in fast fashion.

As the facilitator, give everyone instructions to journal for 10-15 minutes on the top 5% of peak experiences in their life (ie getting married, having children, etc) as well as the bottom 5% of key moments that shaped who they are today.

After time to journal, give everyone 10 minutes to share. This exercise works best in smaller groups like executive team retreats or smaller department-level offsites, and may require 1-2 hours (more than the average icebreaker). Nevertheless, it is incredibly powerful for building deep, meaningful connections among colleagues.

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Find this helpful? What other facilitation notes, session ideas, or resources can the Offsite team create for you? Let us know…

Every company is different, and every offsite has different business objectives, so the team at Offsite is committed to being a resource for you throughout your team retreat planning journey, whether you need agenda templates, budgeting advice, pre/post offsite feedback form prompts, and more.

Email me anytime at jared@offsite.com, or visit offsite.com for client case studies to see how other companies are using Offsite for their team retreat needs.

And of course, whenever you plan offsites in the future, make a free account at offsite.com to search our curated marketplace with hundreds of amazing offsite venues, 20%+ savings on room blocks, meeting space, and more.

Plus, we offer end-to-end offsite planning services if you want a “done for you” experience. See why companies like Buffer, Webflow, 15Five, Linear, HiBob, Metabase, Hampton, and others trust Offsite for their team retreats.

Thanks for reading!

-Jared

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