Running Offsites
Offsites create the space for thinking, bonding, and alignment that daily work crowds out. Done well, they build team cohesion, generate breakthrough ideas, and cement strategic direction. Done poorly, they're expensive retreats that leave everyone more confused than before.
The Guide
4 key steps synthesized from 5 experts.
Design for thinking space, not status updates
The power of offsites comes from pulling people out of their daily routines and creating mental space for different kinds of thinking. Don't fill the agenda with presentations and reports—design for collaborative problem-solving, creative brainstorming, and deep discussion.
Featured guest perspectives
"When you yank people out of their day-to-day routine, you create space, and also you imprint memory... you're basically activating new parts of their brain."— Claire Hughes Johnson
"Laptops down, we're going to spend all day together on a whiteboard. It's like a lost art. People don't use the whiteboards anymore."— John Mark Nickels
Start with connection before diving into work
Human connection makes the work better. Begin offsites with social activities or team-building that helps people see each other as full humans, not just colleagues. This investment pays off in more honest conversations and better collaboration throughout.
Featured guest perspectives
"We start off with just doing something fun... And then after that we talk about strategy. We do workshops on different elements of craft boosting that craft together."— Megan Cook
"They were all fighting... Address team conflict and connection before attempting to implement storytelling or influence workshops."— Donna Lichaw
Use physical tools and enforce device-free sessions
The best offsite work happens with whiteboards, sticky notes, and markers—not slides and screens. Enforce 'laptops down' during working sessions to ensure full presence. Physical collaboration creates shared artifacts and memories in ways that digital collaboration cannot.
Featured guest perspectives
"It was super productive. It was like, laptops down, we're going to spend all day together on a whiteboard."— John Mark Nickels
"Remove the team from day-to-day routines like email to focus on brainstorming."— Claire Hughes Johnson
Create regular cadence rather than one-off events
The best teams treat offsites as a recurring investment, not a special occasion. Quarterly or semi-annual rhythms build compounding trust and provide natural checkpoints for strategic realignment. Each offsite builds on the last rather than starting from scratch.
Featured guest perspectives
"We get everyone together just like every six months... the idea is to have a bit of an onsite."— Megan Cook
"We've actually instituted something we call bursts... the ability for your team generally maybe once a quarter, to just come together to do really high velocity creative work."— Brandon Chu
Common Mistakes
- Filling the agenda with presentations instead of creating space for collaborative work
- Skipping social connection time and diving straight into work content
- Allowing devices and distractions that prevent full presence
- Treating offsites as one-off events rather than building a regular cadence
Signs You're Doing It Well
- Team members reference offsite discussions and decisions months later
- The team leaves with clear, shared commitments they remember without notes
- Relationships strengthened at offsites improve daily collaboration
- People look forward to offsites rather than dreading them
All Guest Perspectives
Deep dive into what all 5 guests shared about running offsites.
Brandon Chu
"we've actually instituted with something we call bursts. So bursts at Shopify are the ability for your team generally maybe once a quarter or whatnot, to just come together to do really high velocity creative work together, to hang out together."
- Schedule quarterly in-person sessions for high-velocity creative work
- Build or use infrastructure to make booking and logistics for these 'bursts' frictionless
Claire Hughes Johnson
"When you yank people out of their day-to-day routine, you create space, and also you imprint memory... you're basically activating new parts of their brain, and then you're also having a group experience that cements a belief system usually, or a set of plans."
- Remove the team from day-to-day routines like email to focus on brainstorming
- Use offsites to collaboratively form plans rather than presenting pre-made ones
Donna Lichaw
"They pulled me aside halfway through the offsite, and they were just like, 'Honestly, storytelling is not going to fix our problems. This is silly.' And what they were able to tell me is that their leaders wanted them to be more effective by having greater influence... what was happening on the ground with these executives was that they were all fighting."
- Address team conflict and connection before attempting to implement storytelling or influence workshops.
John Mark Nickels
"We recently had an all-day Monday thing where eight of us came into the office to talk about future of marketplace, and it was super productive. It was like, laptops down, we're going to spend all day together on a whiteboard. It's like a lost art. People don't use the whiteboards anymore."
- Enforce a 'laptops down' rule for strategic sessions
- Use physical whiteboards to facilitate co-creation and riffing
Megan Cook
"One of the other things we do is we get everyone together just like every six months. So all of the product managers get together in the same place and the idea is to have a bit of an onsite. Now we start off with just doing something fun... And then after that we talk about strategy. We do workshops on different elements of craft boosting that craft together."
- Gather remote teams in person at least every six months
- Start offsites with social activities to build human connection before diving into work
- Utilize internal experts to teach specific craft skills (e.g., growth hypotheses) to the broader team
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