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.
The TL;DR, Prepping For Your Itty Bitty Offsite
December 3 - December 9
Small, But Planning to be Mighty
The word "offsite" tends to conjure up an image of big corporate suited executives at either a hotel conference room or a golf course, talking about synergy and SWOTs.
Screw that. Offsites are for everyone.
No matter your organization's size, corporate-y-ness, or access to golf courses, teams need to enter a different headspace in order to be truly strategic. If you try to envision the future while stuck doing the day-to-day, you're doing Future You a disservice.
An offsite can be three hours in a bar's back corner, it can be a couple two-hour blocks over a weekend, it can be an afternoon in a VR office space...anything that's outside the day-to-day work and intentionally designated to talk big-picture topics.
We're working on an Offsite-in-a-Box guide over here in Learn to Scale land, but here's a few nuggets specifically for a small team.
We Offsite In Order Swing Hard
A small team simply doesn't have the time and money to be inefficient. Doing a lot of little things won't substantially grow your impact: you gotta swing hard on a few things. Picking what to swing at and how hard to swing is exactly what an offsite is designed to thoughtfully do.
Getting Started Is Half The Battle
One of the biggest hurdles a small team has to get over is simply deciding that they need an offsite at all. When you can look at your entire organization at a bistro table, it can feel like you have a lot of agency to do what you want to do: Why do we need a special planning session; let's just get coffee!
However, the point of the offsite isn't just to give yourself agency to make plans- it's designed to orient you into making better plans. If your quarterly strategy is something you kinda talked about at Starbucks last week, it's tempting to go to Starbucks this week and change it...or not follow it at all.
Your team deserves a special space to dream, discuss the best dream, and then say no to the other dreams.
The Other Half Of The Battle
Planning an effective small team offsite starts the same as a big-team offsite: begin with answering these three questions.
A Two-Part Offsite
If you're a small team (2-10 people) where you share decision-making, you could invite the whole crew to an offsite. However, if your small team has a number of contractors/part-time staff, invite them for a portion of the overall offsite. Consider having a second portion where the core offsite attendees present their work for feedback: everyone gets to have input but you don't have to bore (and pay!) your contract graphic designer.
More Offsite Goodies Incoming
We're hard at work organizing an eBook to make offsite planning easy! Stay tuned through the next few TL;DRs where we'll unveil more sneak previews for delicious strategy planning.
A TL;DR from the CRO
Allow yourself to grow out your winter haircut and sink into your shaggy personality.
-Roman Noodles, Chief Ruff Officer
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Rock tumbling update:
Every week I take the most recent batch of stones out of the rock tumbler to put in fresh water and grit. A week of tumbling leaves behind a pretty thick grey slurry that should not go down the drains, lest it harden into concrete.
When it was summer/fall, I would go into the backyard and dump the slurry out on a gravel path and rinse off the rocks with the garden hose. It was a peaceful exercise and I would get delighted when rinsing off the rocks to see how they fared over the week.
Now that it's winter, the hose is shut off, so my water source is my kitchen.
On the 2nd floor.
I could pour the slurry into a bucket, rinse the stones off in the kitchen, and then trudge the bucket down a narrow flight of winding stairs to the backyard.
Or I could just throw the slurry out the window.
I've been throwing it out the window.
Don't tell my downstairs neighbor.
Discretely hucking rock water,
Dan from Learn to Scale
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PS. Even villains listen to music while they focus on their terrible work.
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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