When I started High Five, the decision to be a 100% remote company wasn’t just a trend – it was a strategic choice. It allowed us to hire the best talent, regardless of location, and operate with the agility that early-stage startups need to survive.
But I quickly learned that building a company is one thing, building a culture across different cities and time zones is another challenge entirely.
It doesn’t happen by accident. A thriving remote culture is built with intention, one deliberate decision at a time. It’s about replacing spontaneous office interactions with thoughtful, structured rituals and replacing physical presence with deep, psychological trust.
This playbook shares the hard-won lessons and practical strategies we used at High Five to build a remote team that is connected, engaged, and performing at its peak.
Benefits and Challenges of Remote Work
Before diving into the “how,” it’s important to be clear-eyed about the “why.” Embracing remote work comes with incredible advantages, but also a unique set of challenges you must proactively manage.
The Benefits are Game-Changing:
- Access to a Global Talent Pool: You’re no longer restricted to a 30-km radius around an office. You can hire the absolute best person for the job, wherever they are.
- Increased Autonomy and Flexibility: Empowering your team to work when and how they’re most productive is a massive driver of job satisfaction and retention.
- Reduced Overhead: Lower costs on office space and utilities mean you can invest that capital back into your product and people.
But the Challenges are Real:
- Culture and Connection Can Fade: Without the physical space to bond, team camaraderie can weaken, and a sense of shared identity can be hard to build.
- Communication Becomes More Complex: The risk of misinterpretation, information silos, and “out of sight, out of mind” bias is significantly higher.
- The Threat of Burnout is Constant: The lines between work and home blur, making it difficult for employees to switch off, which can lead to exhaustion.
The rest of this playbook is designed to help you maximize the benefits while tackling these challenges.
1. It Starts with Hiring “Remote-Ready” People
You can have the best processes in the world, but they’ll fall flat without the right people. In a remote setting, certain traits are non-negotiable. We learned to screen for more than just skills; we screen for the remote-ready DNA.
- Proactive Communicators: Look for people who naturally over-communicate. In an office, you can see if someone is stuck. Remotely, silence is a black hole. Ask candidates how they’d handle a situation where they’re blocked on a task and their manager is offline. Their answers will reveal their communication instincts.
- Self-Disciplined Drivers: Remote work requires a high degree of autonomy. You need people who can manage their own time, prioritize tasks, and stay motivated without a manager looking over their shoulder. Ask about a long-term project they managed independently.
- High Trust & Low Ego: Trust is the currency of a remote team. You need individuals who are reliable, transparent when they make mistakes, and celebrate the team’s success over their own.
2. Document Everything
Your company’s documentation is about your central nervous system. It’s the single source of truth that enables asynchronous work and empowers everyone to make decisions independently.
- The Company Handbook: Create a living document that covers everything from your company’s mission and values to communication etiquette (e.g., “What goes in Slack vs. email?”), and meeting protocols.
- Meeting Cadence & Notes: Every meeting should have a clear agenda shared beforehand and detailed notes with action items shared afterward. This ensures alignment for those who couldn’t attend.
- Project Hubs: For every project, create a central page that links to all relevant briefs, designs, research, and decisions. This saves countless hours of searching through Slack threads.
3. Daily, Weekly & Monthly Rituals
You can’t replicate the office water cooler, but you can create new spaces for connection. The key is consistency and intentionality.
- Daily Rituals:
- The First Five: We start every day by sharing our “First Five” in a dedicated Slack channel: 1) How I’m feeling (a simple emoji works), 2) My top priority for the day, 3) Any potential blockers, 4) A shoutout to a teammate. It takes five minutes but creates incredible daily alignment and connection.
- Weekly and Monthly Rituals:
- Virtual Boba Hangouts: We block out 30 minutes every Friday for a non-work video call. No agenda, just casual conversation. Sometimes we play online games, other times we just chat. It’s our version of the team lunch.
- Mini Awards: Once a month, during our all-hands, we dedicate time to “Mini Awards.” Anyone can nominate a teammate for an award, from “Fastest Slack Replier” to the “Most Helpful Human Award.” It’s a fun, low-stakes way to build a culture of recognition.
4. Arm Your Team with the Right Tools
Tools should reduce friction, not add noise. Be intentional about your tech stack and create clear guidelines for how each tool should be used.
- Communication Hub: Slack is our company chat. We have clear channel hygiene (#general for announcements, #kudos for celebrations, #random for fun).
- Collaboration & Documentation: Notion is our company’s brain. It’s where our handbook, project hubs, and meeting notes live. For real-time brainstorming, Miro is our virtual whiteboard.
- Presence & Connection: Gather.town, as a virtual office, has been a game-changer for bringing a sense of physical presence and spontaneity to our remote workdays.
5. Invest in Your People
In a remote setup, you lose the visual cues of a teammate looking stressed or burnt out. Growth conversations can also feel less organic. A deliberate focus on employee well-being and career development is crucial for long-term retention and building a sustainable culture.
- Combat Burnout Proactively: The line between work and home disappears in a remote setting. Introduce policies that protect your team’s personal time.
- Set Clear Communication Hours: Establish core hours but also “no-messaging” times to let people fully disconnect.
- Mandate Time Off: Encourage and, if necessary, mandate that people take their vacation days. Lead by example.
- Offer Wellness Stipends: Provide a monthly budget for gym memberships, mental health apps, or anything that helps your team recharge.
- Create Clear Growth Paths: Don’t let “out of sight, out of mind” apply to promotions.
- Structured Career Ladders: Create and share documents that outline what it takes to get to the next level in any given role.
- Regular 1-on-1s: Ensure managers are having dedicated, non-project-related check-ins to discuss career goals.
- Learning & Development Budget: Allocate funds for each employee to spend on courses, books, or conferences that help them grow their skills.
Building a world-class remote culture is a continuous process of experimentation and refinement. But by hiring the right people, documenting everything, creating intentional rituals, using the right tools, and investing in your team’s well-being, you can build a team that is not only productive but also deeply connected, no matter where they are in the world.
