Running Offsites

Running Offsites

Help the user plan and run effective team offsites using frameworks from 5 product leaders.

How to Help

When the user asks for help with offsites:

1. Clarify the purpose - Ask what outcome they want from the offsite (strategy, connection, planning) 2. Assess readiness - Determine if there are underlying team issues that need addressing first 3. Design the structure - Help them balance work sessions with social connection 4. Remove friction - Guide them on logistics that make offsites productive

Core Principles

Use "bursts" for remote teams

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." Remote-first companies should schedule quarterly in-person sessions for high-velocity creative work that's difficult to do asynchronously.

Offsites create space and imprint memory

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.

Address conflict before soft skills training

Donna Lichaw: "They pulled me aside halfway through the offsite, and they were just like, 'Honestly, storytelling is not going to fix our problems.'" Offsites focused on soft skills may fail if there are underlying interpersonal conflicts. Address team connection and conflict before attempting workshops on influence or communication.

Go laptops-down and use whiteboards

John Mark Nickels: "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." Deep strategic work requires removing digital distractions. Physical collaboration tools like whiteboards facilitate co-creation and riffing.

Balance social connection with strategy

Megan Cook: "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." Start offsites with social activities to build human connection before diving into work. Use semi-annual gatherings to combine strategy alignment with skill-building.

Questions to Help Users

• "What's the single most important outcome you want from this offsite?"
• "Are there underlying team conflicts that might undermine the offsite agenda?"
• "How will you ensure people disconnect from day-to-day work during the offsite?"
• "What's the right balance between work sessions and social time for this team?"
• "When did the team last meet in person? What worked well and what didn't?"

Common Mistakes to Flag

• Packed agendas - Scheduling every minute without leaving space for organic conversation
• Soft skills over hard problems - Running workshops on communication when the real issue is conflict or strategy
• Not disconnecting - Allowing email and Slack to compete with offsite activities
• Too infrequent - Waiting too long between in-person gatherings for remote teams
• Presenting rather than creating - Using offsites to present pre-made plans instead of collaboratively building them

Deep Dive

For all 5 insights from 5 guests, see references/guest-insights.md

Related Skills

• running-effective-meetings
• running-decision-processes
• post-mortems-retrospectives

Running Offsites - All Guest Insights

5 guests, 5 mentions

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Brandon Chu

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."

Insight: Remote-first companies should use short, high-intensity in-person 'bursts' to handle creative work that is difficult to do asynchronously.

Tactical advice:

• Schedule quarterly in-person sessions for high-velocity creative work
• Build or use infrastructure to make booking and logistics for these 'bursts' frictionless

Timestamp: 20:31

Claire Hughes Johnson

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."

Insight: Offsites are essential for creating mental space and imprinting collective memory that cements team alignment.

Tactical advice:

• 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

Timestamp: 01:12:53

Donna Lichaw

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."

Insight: Offsites focused on soft skills like storytelling may fail if there are underlying interpersonal conflicts or a lack of genuine influence among leadership.

Tactical advice:

• Address team conflict and connection before attempting to implement storytelling or influence workshops.

Timestamp: 00:06:56

John Mark Nickels

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."

Insight: Deep strategic work requires 'defragging' the day and removing digital distractions in favor of physical collaboration tools.

Tactical advice:

• Enforce a 'laptops down' rule for strategic sessions
• Use physical whiteboards to facilitate co-creation and riffing

Timestamp: 00:32:10

Megan Cook

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."

Insight: Use semi-annual offsites to balance social connection with intensive strategy alignment and skill-building workshops.

Tactical advice:

• 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

Timestamp: 00:10:29