About

Navigation

Chapter 9

Remote Events Gatherings

Creating virtual and in-person experiences that strengthen relationships and enable collaboration.

Reading time: 21 minutes

Building Connection Beyond Screens

“The most effective remote companies aren’t remote 100% of the time. They’re remote by default with purposeful in-person connection.”

While daily work happens asynchronously, intentional synchronous events remain valuable for building relationships and alignment. In my experience, I’ve discovered that deliberate gatherings - when designed with clear purpose and thoughtful execution - create exponential returns in team cohesion, trust, and shared understanding.

In this chapter, we’ll explore how to design these experiences to maximize their impact, whether they’re virtual or in-person.

The Purpose of Remote Events

Before diving into implementation details, let’s clarify why remote events matter in the first place:

Why Gather at All?

Remote events serve specific purposes that asynchronous work can’t fully address:

  1. Relationship building - Creating human connections beyond work transactions
  2. Alignment creation - Developing shared understanding of direction and priorities
  3. Creative collaboration - Generating ideas through real-time interaction
  4. Cultural reinforcement - Strengthening values and shared identity
  5. Celebration and recognition - Marking achievements and honoring contributions

When designed intentionally, these events provide the social glue that helps remote teams withstand challenges and maintain cohesion despite physical distance.

Just as good conventions free developers to focus on business logic, well-designed gatherings create the relational foundation that enables remote teams to focus on building great products together.

Common Pitfalls in Remote Team Events

Many remote organizations struggle with creating effective gatherings:

1. The Awkward Happy Hour

2. The Half-Present Participant Problem

3. Hybrid Meeting Inequality

4. Timezone Exclusionary Scheduling

5. Technical Friction Fatigue

⚠️ Warning
Even well-designed remote events fail when technical issues prevent equal participation.

How-to: Create Meaningful Team Events

Let’s start with team-level virtual events before exploring company-wide and in-person gatherings:

1. Design for Equal Participation

The fundamental principle for all remote gatherings is ensuring everyone can participate equally, regardless of location.

Implementation approach:

1. Equal technical setup

2. Deliberate inclusion practices

3. Mixed-mode considerations

🎯 Concrete Example
For quarterly planning sessions, you might initially try having part of the team in a conference room with remote participants on screen, only to find this creates a clear in-group/out-group dynamic where remote voices are less heard. Switching to an 'all-digital-first' approach where even people in the same physical location join from individual devices can dramatically improve engagement from everyone. For the final social portion, the in-person group can gather while remote participants join in ways that work for them.

This ensures the experience works well for everyone rather than optimizing for some at the expense of others.

2. Technical Setup Matters Enormously

The quality of the technical experience directly impacts the quality of connection possible.

Implementation approach:

1. Invest in high-quality audio

2. Optimize video when used

3. Provide technical support

4. Choose appropriate platforms

🎯 Concrete Example
You might learn the hard way that poor audio quality is the fastest way to make remote participants feel excluded. Providing a standard audio setup (specific headset model) to every team member as part of their onboarding can make a significant difference. For important team events, implementing a 'tech check' 15 minutes before the official start where everyone confirms their audio is working properly can prevent frustrating delays. This small investment can dramatically improve your virtual gatherings.

This technical foundation creates the infrastructure that enables effective interaction.

3. Structure Interaction Intentionally

Thoughtful interaction design creates more engaging and productive remote events.

Implementation approach:

1. Use tools that allow equal contribution

2. Create explicit opportunities for input

3. Break larger groups into smaller discussion units

4. Design for different interaction preferences

🎯 Concrete Example
For monthly all-hands meetings, try moving from a typical presentation format to a structured approach called '3-3-3': 3 minutes of presentation, 3 minutes of small group discussion in breakout rooms, and 3 minutes of full-group discussion and Q&A. This pattern can repeat for each major topic. Engagement often skyrockets, allowing you to hear from voices that were previously silent. Sending the agenda in advance with pre-meeting questions also allows for asynchronous input from those who process information differently.

This structured approach creates predictable patterns that enable more effective participation.

4. Balance Synchronous and Asynchronous Components

The most effective remote events combine real-time interaction with asynchronous elements.

Implementation approach:

1. Design events with pre-work and post-event activities

2. Record key sessions for those who cannot attend live

3. Create artifacts that capture value beyond the live experience

4. Design for time zone equity

🎯 Concrete Example
For quarterly strategic planning, consider developing a three-phase approach: 1) Pre-work: Team members review objectives and submit initial thoughts asynchronously over a three-day period, 2) Synchronous session: A 2-hour video call to discuss key questions and make decisions, 3) Post-work: Documentation of decisions and implementation planning in collaborative documents over the following week. This approach respects everyone's time while ensuring all voices contribute to your direction.

This balanced approach finds the right mix of components to create the most effective overall system.

When to Bring Everyone Together

Physical gatherings remain valuable when:

1. Onboarding new team members

2. Strategic planning and vision-setting

3. Building relationships outside of work contexts

4. Complex problem-solving requiring intensive collaboration

When designing in-person gatherings, make them count. Focus on activities that truly benefit from physical presence, rather than work that could be done remotely.

This selective approach focuses resources where they create the most value rather than trying to do everything.

How-to: Implement Meaningful IRL Events for Remote Teams

Investing in in-person gatherings is paradoxically one of the most important aspects of successful remote organizations. When implemented correctly, these events strengthen culture, build relationships, and ultimately improve remote collaboration.

1. Annual or Bi-Annual Company Retreats

Company-wide gatherings create foundational connection and alignment.

Implementation approach:

1. Focus on relationship-building and strategic alignment

2. Alternate locations to distribute travel burden

3. Balance structure and flexibility

4. Capture and extend value

🎯 Concrete Example
Consider structuring bi-annual team retreats with a consistent pattern: Day 1: Arrival and welcome activities, Day 2: Strategic alignment and cross-team collaboration, Day 3: Team-specific deep dives and problem-solving, Day 4: Structured social experiences and celebration, Day 5: Reflection and action planning. This consistent structure creates clear expectations while allowing flexibility in the specific activities. Alternating between European and North American locations distributes travel burden, while providing extra travel days for team members coming from greater distances ensures fairness.

This comprehensive approach addresses all aspects of the experience rather than leaving important elements undefined.

2. The ROI of In-Person Events

These gatherings are significantly more cost-effective than maintaining physical offices.

Implementation approach:

1. Calculate the financial case

2. Measure the impact on collaboration quality

3. Design experiences for maximum return

4. Communicate the strategic importance

🎯 Concrete Example
You might calculate that twice-yearly week-long company retreats cost approximately 15-20% of what you'd spend on office space, utilities, and commuting costs for the entire company. Yet the impact on team cohesion and productivity is substantial. Tracking team effectiveness metrics before and after retreats consistently shows improvements in cross-team collaboration, issue resolution speed, and reported job satisfaction in the months following each gathering.

This ROI-focused approach makes strategic investments that pay dividends through enhanced effectiveness.

3. Project Kickoff Gatherings

For larger organizations, bringing project teams together at launch creates alignment and relationship foundation.

Implementation approach:

1. Focus on building shared understanding

2. Create artifacts that serve as reference points

3. Establish working agreements and communication patterns

4. Develop personal connections

🎯 Concrete Example
When launching significant new initiatives, consider bringing the core project team together for a three-day kickoff. The first day can focus on building shared understanding of the problem space and creating personal connection. The second day might be dedicated to aligning on approach and making key decisions. The third day then transitions to remote work planning, establishing norms, tools, and practices the team will use for ongoing collaboration. Teams often report that this initial investment dramatically reduces miscommunication and accelerates progress in the critical early stages.

This focused approach creates the foundation that enables effective work going forward.

4. Department-Level Connect Events

For companies with 50+ people, organizing department gatherings creates deeper connection within functional areas.

Implementation approach:

1. Rotate throughout the year

2. Focus on team building and long-term planning

3. Cross-pollinate between departments

4. Create balance with company-wide events

🎯 Concrete Example
Each department (Engineering, Product, Marketing, etc.) might hold a 3-day in-person gathering once per year, staggered throughout the calendar. Engineering could meet each January to plan architecture evolution, while marketing teams gather in March for strategy development, and so on. These focused gatherings allow for deeper department-specific work while company-wide retreats focus more on cross-functional alignment and relationship building.

This layered approach creates appropriate structures at different levels of the organization.

Best Practices for IRL Events

To maximize the value of in-person gatherings:

1. Plan Activities That Build Lasting Relationships

Implementation approach:

1. Design experiences that reveal authentic selves

2. Balance structured and unstructured time

3. Create shared memories

4. Focus on inclusion

🎯 Concrete Example
You might find that shared experiences with elements of novelty, challenge, and play create the strongest lasting bonds. For example, cooking classes where mixed teams prepare a meal together, guided outdoor adventures appropriate to the location, and creative workshops led by local artists often work well. These experiences create conversation topics and shared references that continue long after the in-person gathering ends.

This intentional approach recognizes that human connection is fundamental to effective collaboration.

2. Respect Personal Boundaries

Implementation approach:

1. Make accommodations for those who can’t travel

2. Balance work and social components

3. Consider diverse needs and preferences

4. Establish clear expectations in advance

🎯 Concrete Example
Being very explicit about which parts of in-person gatherings are required versus optional can make a significant difference. Core working sessions and team meals might be required, while evening activities and recreational components can be optional. Providing quiet spaces for those who need breaks from social interaction and explicitly communicating that taking care of personal needs is encouraged and respected helps everyone participate comfortably.

This balanced approach provides clear structure while respecting individual needs.

Maintaining Connection Between Gatherings

In-person events create relationship foundations, but ongoing connection requires deliberate practices:

1. Create Rituals That Transcend Physical Distance

Implementation approach:

1. Establish recurring team rituals

2. Balance structured and spontaneous interaction

3. Celebrate milestones and achievements

4. Acknowledge life events

🎯 Concrete Example
Establishing 'Friday Wins' as a weekly ritual can be powerful, a 30-minute optional gathering where people share both professional and personal achievements from the week. The format can be lightweight: a quick round of shout-outs followed by anyone who wants to share something they're proud of or grateful for. This simple practice creates regular connection points between more substantial in-person gatherings.

This continuity approach creates predictable patterns that make connection natural and expected.

2. Leverage Digital Tools Thoughtfully

Implementation approach:

1. Create digital spaces for social connection

2. Implement virtual social activities

3. Facilitate one-on-one connections

4. Focus on human stories

🎯 Concrete Example
Tools like Donut can randomly pair team members for virtual coffee chats every two weeks. With participation being opt-in, you might find about 80% of your team chooses to join. These 15-30 minute conversations create cross-team connections that wouldn't happen organically and help maintain the relationships that form during in-person gatherings.

This thoughtful use of technology focuses on using the right tools for the job rather than technology for its own sake.

Moving Forward

Definition of Done

You’ve successfully designed effective remote events and gatherings when:

  1. Team members feel genuinely connected despite physical distance
  2. In-person gatherings create lasting impact on remote collaboration quality
  3. Virtual events engage participants fully rather than feeling like obligations
  4. People across locations and time zones experience equal inclusion
  5. The organization invests appropriately in both in-person and virtual connection
  6. Team members maintain relationships between formal gatherings
  7. New people integrate smoothly into the team culture
  8. The organization values human connection as essential infrastructure

Recap

Remote work offers a chance to fundamentally rethink how we build software and organizations. When you embrace its unique characteristics rather than fighting them, you unlock capabilities that traditional co-located teams struggle to match: 24-hour development cycles, global talent pools, and resilience to disruption.

The startups that will thrive in this new landscape aren’t those with the most sophisticated remote tools or the strictest monitoring systems. They’re the ones building cultures of trust, systems that reduce friction, and communication patterns that transcend time zones.

As a founder or executive, your job isn’t to control remote work—it’s to harness its inherent advantages while thoughtfully addressing its challenges. Done well, remote-first can become your competitive edge in attracting talent, moving quickly, and building an organization that’s resilient by design.

Final Thoughts

This completes our journey through remote excellence, but it’s really just the beginning of yours.

You now have a comprehensive framework for building distributed teams that unlock capabilities traditional co-located teams struggle to match. The 24-hour development cycles, global talent pools, and resilience that remote-first organizations enjoy are natural outcomes of thoughtful systems design applied to human collaboration.

The path forward isn’t perfect implementation of every technique. It’s selecting approaches that fit your context, experimenting with what works, and continuously refining based on real feedback from real work.

Remote work, done thoughtfully, creates possibilities that don’t exist in traditional environments. Your remote journey starts with trust as your operating system and evolves into something more powerful: an organization designed around human potential rather than physical proximity.

Conclusion →