The TL;DR, Packed With 5 Icebreakers for Offsites


A bi-weekly roundup of zesty ways to be creative
October 29 - November 11

Start Stronger

While writing 3 Key Elements for an Executive Offsite, I was paging through Gamestorming while eating lunch. It's a workbook that explores creative ways to start, facilitate, and close effective meetings.

Some people spend their lunch break watching TikTok. Some people read facilitation manuals

To augment the executive offsite post, here are five juicy techniques from Gamestorming to kick off a strategy session.

1. Storyboard

Pick a topic for the strategy session, break participants into small groups, and have them draw/describe a narrative. Give them the goal to tell a feel-good story, "The topic of the story is 'The Ideal Future for [blank]" where [blank] is the topic for the strategy session. Give participants 20-25 minutes to draw and plot out the story, then have everyone share their tale. Make it as visual as possible!

2. The Anti-Problem

Before the session, identify a real problem that needs to be solved. During the session, challenge participants to solve the opposite problem with whatever outlandish ideas they can generate. For example,

  • If the problem is "Improve sales conversion," the anti-problem would be "Get customers to avoid buying the product"
  • If the problem is "How to provide useful feedback to team members," the anti-problem would be "How to provide utterly useless feedback to team members"
  • If the problem is "Build a feature by a deadline," the anti-problem would be "Prevent the team from hitting their deadline"

3. Cover Story

This is an adaptation of Storyboard, but instead of telling a story, participants are asked to envision a future state that is so stellar that it puts your organization on the cover of a well-known magazine. Attendees should try to hit on the following components:

  • Cover- The BIG story of the success
  • Headline- The substance of the cover story
  • Sidebar- Interesting facets of the cover story
  • Quotes- Anyone's personal perspective on the cover story
  • Images- Something that captures the spirit of the cover story

Protip: Actively discourage "realistic" ideas: this is an open-ended creative-thinking exercise, not a gameplan to get on High Times.

4. Ransom Your Values

To help make corporate values more real, this icebreaker encourages participants to build a vision board using magazine cutouts, similar to pop-culture ransom notes. Provide a breadth of magazines, scissors, glue, and poster paper for participants to team up and translate corporate values into imagery. To help get started, tell the players that the assignment is twofold:

  1. Use images and words from magazines that, in their eyes, describes a company value.
  2. Share a work-related story that's indicative of those values
  • For example, an image of a turtle may represent patience and longevity values. For the anecdote, the group may share an example of when an attractive but high-risk project was not pursued.

5. Challenge Cards

Select a core topic and break participants into two teams- Challenge Team and Solution Team. Have the Challenge Team privately brainstorm problems/challenges and write them on index cards. Have the Solution Team privately brainstorm features and strengths of a product/solution and also write them on index cards.

Once the teams have generated a stack of cards, they duel! The Challenge Team picks a card and plays it, describing a scene or event where the issue might realistically arise. The Solution Team must then pick a card from their deck that addresses the challenge. If the challenge isn't met or met well (a judge can help!), the Challenge Team gets a point. If the solution is adequate, the Solution Team gets a point. All poorly solved challenges get tabled for a more in-depth conversation to draft new solutions.

For example, the core topic "Why people want to work at our organization" may generate a challenge card like "Work/Life Balance." The Challenge Team throws down the card and says, "I'm a candidate and care deeply about my work/life balance." The Solution Team needs to pull a relevant solution card to beat the challenge card, such as, "We provide flexible work arrangements since we are a fully-remote organization."

Aren't Icebreakers Fun?

With all of these icebreakers, a healthy debrief afterwards is a great way to pivot the session from fun to functional. Let me know what you think of these icebreakers- are they something you'd be willing to try for your next strategy session?


A TL;DR from the CRO

Find that sunny spot and put your head into it.

-Roman Noodles, Chief Ruff Officer


ROCK TUMBLING UPDATE

My saga learning how to tumble rocks continues. The last time was a 5/10, which you can see kajumbled on the right side. This batch is a 7/10.

I see rock tumbling as a metaphor for constant improvement and iteration: if you're not pleased, form a hypothesis, get a new batch of experiences, and tumble them again.

My hypothesis with my first batch was that the different kinds of rocks kept them from uniformly getting shiny. To test, this batch was all the same type- Dragon's Blood. They got much more rounded and shiny, but only a few got truly glossy.

This is what we call "important business updates" from Learn to Scale.

Hypothesis for the next batch: remove weird shaped stones that may impede the good ones from getting truly shiny.

Sacrifice the weak for the strong to survive.

Guess there's another metaphor here.

Keep breaking the ice and purging the weak,

Dan from Learn to Scale


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PS. I'm gonna bring back that Teddy like I'm Roosevelt!

Dan Newman

I help organizations build AI fluency and governance that actually changes behavior — not the kind that lives as a PDF on a Notion page. 19 years onboarding humans to strange new places (startups, scaling tech, enterprise agencies like GroupM and WPP) gave me a head start when AI showed up as just another strange new place. The TL;DR is my biweekly newsletter for leaders thinking through what AI means for their people.

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