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Capture the Flag: Company Edition

Summer brings many amazing things: watermelon, Fridays where no one actually works, office outfits meant to minimize the extreme sweatiness that results from your morning commute,* interns that - net-net - create negative value and more work for you, and…..the annual company offsite / picnic / workshop / team retreat / boondoggle.

Yes, you know. That event where everyone gets bussed (or flown, if you’re fancy like that) to some spot away from the office to spend a few hours or a few days bonding, inculcating new people with the company culture, talking long-term vision and future strategy, and most importantly, keeping the underage interns away from the alcohol.

As a manager, we’re often required to be camp counselors, I mean, to help organize and structure these offsites. We’re tasked with planning agendas that are meaty but light-hearted; introspective but forward-looking; accomplishment-oriented but “fun.” It’s a tall order.

Recently, one of my favorite people at one of my favorite start-ups remarked: “I wish there were a list of decent summer offsite activities I could just choose from.” Well. Wish granted. Here is a list - in no particular order - of some of my favorite offsite activities that can be adapted for teams of 8 to teams of 80. There are plenty more activities, but I’m hoping that this list will be helpful if you get stuck needing to fill a 60 minute slot in the agenda...and you’ve already planned a game of capture-the-flag.

A Highly Unscientific, Not Data-Driven List of Offsite Activities

1. Journey Lines (30 min - 60 min)

  • Goal: reflect on the past year individually; collectively chart the highs and the lows of the past year as an organization (see commonalities and themes)

  • How it works: you have to embrace the cheesiness of this one. First, each team member individually draws his / her journey line for the year - the chart of the highs and the lows of the year with labels. Then, in groups of three or four, each team member talks through his journey line with his small group.

  • The group identifies any collective themes or patterns (e.g., we all had a low point in November)

  • If you’d like, you can then create a company journey line plotting the big wins and low points throughout the year.

  • Here’s my journey line from this past year as an example:

2. StrengthsFinder (30 min - 90 min)

  • Goal: get to know more about yourself and your team members; identify gaps or themes that may impact your company culture or way of operating.

  • How it works: prior to the offsite, everyone takes the StrengthsFinder assessment (I do the 5 strengths one - link here) and sends the results to someone who aggregates them (result aggregator here).

  • In groups of three or four, each team member shares her strengths, what she found surprising, and how this comes out in her day-to-day work.

  • Then, as a company, reflect on the company’s aggregated strengths. Reflect on what this says about the company, what are the gaps (if any) or themes, and if / how we should change aspects of how we do business to reflect those themes.

  • For example, what does it mean if we have a lot of “strategic thinkers” but few folks with “executing” as a key strength? Do we build more process into our work to hold ourselves accountable to executing?

3. Innovation Exercise (30 min - 120 min)

  • Goal: think innovatively about your business or product; get to know another side of team members.

  • How it works: as a pre-read, have your team read the HBR Article on Innovation, and as a group, watch the youtube video: Where Good Ideas Come From.

  • In groups of 6 or 7 - talk through your individual differences in the group (e.g., your past job experience, college majors, hobbies) and how those experiences have shaped you / how you work.

  • Each group chooses two experiences or backgrounds that are most interesting (e.g., French horn player & summer lifeguard) and talk through how a practitioner from these disconnected fields would say about your current business or product.

  • Then, come up with two innovations (to your business model, process, product) based on these two experiences. Teams illustrate these two innovations on a flip chart.

  • Whole company votes on their favorite innovations.

  • (For a slight twist, you can have people pick their favorite all-time company and have them come up with innovations through the lens of their favorite company - e.g., how would Trader Joe’s approach our company’s business model or product?)

  • (Or, for something longer, consider running a condensed 2-hour Design Sprint on a relevant company challenge).

4. Think & Drink (30 min - 90 min)

  • Goal: encourage diversity of thought and backgrounds; allow for respectful dissent and disagreement within a team; think about a tangential but important topic that may impact your business.

  • How it works: as a pre-read, send along a few articles that cover a topic that has multiple points-of-view. Come up with two question prompts that have yes / no answers.

  • In small groups (4-6 seem to work best), debate the topic, and by the end of the debate, have everyone in the group decide where they fall (yes / no) on each of the two questions.

  • Create a handy-dandy 2x2 matrix to capture peoples’ opinions.

  • If time, you can create a huge 2x2 matrix on the ground with tape and have the whole company physically stand where they fall. You could then have an open debate with the company.

  • Here’s an example of a Think & Drink matrix I was part of a few year’s back that debated the current approach to data collection, whistleblowing and surveillance…..

5. Fuzzy-wuzzy All-company Feedback

  • Goal: provide all team members positive feedback that makes them feel glad to be part of the team!

  • How it works: this works for max 30 people at a time (so you may need to do it by team or by functional area). Everyone has a pile of notecards. One-by-one, a team member stands up. For 30 seconds, everyone else writes down one piece of positive feedback for the person (e.g., why he / she is a great leader, a contribution s/he has made to the company, a wonderful personality trait, how this person has personally impacted the feedback giver, etc.)

  • Collect the notecards, move to the next person who stands up for 30 seconds. At the end of the exercise, each person gets his pile of feedback.

  • This exercise is really powerful and also helps people realize strengths they might not know they have.

6. Trust Falls

So, these are just a few of my favorite agenda-fillers for the all company off-site. Have any good activities you’ve done in your organization for your annual boondoggle? Please share below!

*For the profuse sweaters out there (myself included), especially for those of us in excessively muggy climates: sweat pads.


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