Effective documentation is the backbone of any successful remote team. It streamlines communication, reduces redundant questions, and ensures alignment across globally distributed teams. Yet, many organizations struggle with maintaining documentation that is both useful and up-to-date.
In the latest chapter of the Running Remote Playbook, Kasia Triantafelo, Head of the Running Remote community, deep dives into the art of documentation, exploring best practices, tools, and real-world strategies from top remote-first companies. This chapter is designed to help leaders create a robust documentation culture that fosters transparency, efficiency, and collaboration.
In this Chapter, we’re covering:
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Best practices for creating effective documentation
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Strategies for keeping documentation up-to-date
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Tools for documentation management
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Examples of real-world handbooks
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Ways to measure documentation effectiveness
Best practices and lessons learned on documentation
1. Start Simple – “JJ” Jessica Reeder:
Don’t overcomplicate things—start by gathering the information that’s already spread across inboxes, shared folders, and team chats. Chances are, you’ve already documented a lot more than you realize. Begin by auditing existing communication and resources, including emails, slide decks, meeting notes, and Slack discussions.
“No matter where you’re starting from, you’ve already written down a significant amount of useful information.” – “JJ” Jessica Reeder
2. Make it less intimidating – Tim Burgess:
For many, documentation feels like a chore rather than a joy. Tim emphasizes that simplicity and an incremental approach can make a big difference. Instead of striving for perfection, start small and allow your documentation to evolve organically over time.
“First time something breaks, you fix it and move on. Second time, jot down a few bullet points in a doc. By the third time, flesh it out more. This way, you end up with a solid document without wasting time on rarely-used content.” – Tim Burgess
3. Address documentation at three levels: individuals, teams, and the organization – Ryan Chartrand:
“Don’t just send them your playbook and call it a day.” – Ryan Chartrand
Ryan stresses the need to address documentation at three levels:
- Individual: Provide personalized support and set clear expectations for new hires around documentation.
- Team: Understand each team’s unique needs and align documentation practices accordingly. For example, “trying to convince a Sales team that loves phone calls to suddenly instead start documenting everything in Slack and Confluence isn’t likely to go well.”
- Company: Bake values like transparency and proactiveness into the culture to strengthen documentation practices.
4. Start early – Diolinda (DiDi) Vaz, Kaylie Boogaerts:
“Setting explicit norms around documentation early—as early as in job expectations—builds a strong foundation.” – Diolinda (DiDi) Vaz.
Kaylie shares that at Checkly, “they prepare offer overviews in Notion and share the page after the call, setting expectations upfront. We say one sentence about how we’re heavy Notion users, so we also set up the offer in Notion. It sets the tone super early on.”
Kaylie Boogaerts also suggests embedding documentation practices in onboarding workflows & communications to help cultivate a culture of continuous improvement. At Checkly, the third sentence in their “Welcome Aboard” guide explicitly encourages employees to update outdated or unclear documents.
5. Don’t assume prior knowledge – Tim Burgess:
Tim advises making your documentation so clear that “someone could walk in off the street and follow it.” This includes:
- Avoiding jargon or assuming expertise.
- Updating out-of-date screenshots or instructions as you spot them.
“Leave every document better than you found it.” – Tim Burgess
6. Documentation is a collaboration effort – Susannah Houk:
Strong documentation practices require teamwork. At Church Media Squad, as shared by Susannah Houk they:
- Document workflows as they’re developed to ensure alignment.
- Use templates and playbooks (e.g., onboarding guides) to maintain consistency.
- Encourage feedback and contributions to improve processes starting during onboarding.
7. Leverage AI for efficiency – Alina Jesien:
At Ergeon, they enhanced documentation by creating an AI assistant bot in Slack that focused on HR and People policies. Staff can message the bot in any language to get instant answers on topics like PTO or wellness funds.
In its first quarter, this bot reduced HR policy questions by over 75%, enabling the People team to focus on innovation, as shared by Alina Jesien.
8. Document decisions effectively – Kaylie Boogaerts, “JJ” Jessica Reeder:
“Effective decision documentation can reduce meetings, improve transparency, and enhance cross-team coordination.” – “JJ” Jessica Reeder
Kaylie Boogaerts advises against using platforms like Slack for decision documentation. “Instead, store decisions in dedicated tools like Notion or Shortcut, where they’re easier to track and find.”
“JJ” Jessica Reeder notes the challenges of documenting decisions with the right level of granularity. Effective decision documentation can reduce meetings, however, over-documentation can lead to inefficiency. JJ suggests looking to systems like git-style code trackers for inspiration, while recognizing their complexity for non-technical teams.
9. Foster a documentation-first culture – Chase Warrington:
Chase Warrington emphasizes that building a documentation-first culture is not a one-time effort but an ongoing commitment. Leaders play a crucial role by setting an example and demonstrating the value of documentation. Clear objectives, regular reinforcement of its importance, and proper training ensure team members have the tools they need to document effectively. At Doist they recognize and celebrate contributions to documentation which fosters engagement, while integrating documentation into daily workflows encourages consistency.
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BONUS
Documentation tools used by remote companies that are part of the Running Remote community:
Running Remote’s community members rely on a variety of tools to keep their documentation organized:
- Notion (used by 50% of members by companies like Checkly , Float.com, Church Media Squad, MailerLite, Running Remote, dbt Labs, Wild Audience, Hostaway , Block, Freedom, Offsite and Fillout among others)
Notion is an all-in-one workspace that combines notes, wikis, and databases, making it an excellent tool for documentation and knowledge management. it offers flexibility through custom templates, real-time collaboration, and powerful integrations. - Confluence (used by 23% of members by companies like Testlio, Velir, Time Doctor, Balsamiq, Cro Metrics, Growens, among others)
Atlassian’s confluence is a widely used documentation platform for teams to create, share, and manage content. it supports structured pages, team spaces, and version control, making it ideal for maintaining company knowledge bases. - Other tools mentioned: Outline, Haystack, Slite , Coda, Knowledge Architecture, SharePoint, Unily, Slab, Google Docks, Discourse, Unily, ClickUp.
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Download the full chapter to access in-depth insights, practical templates, and case studies from industry leaders. Whether you’re looking to streamline documentation, improve asynchronous communication, or enhance onboarding, this playbook equips you with the knowledge and tools to build a sustainable, high-performing remote team. your remote team.
📥 Download the complete playbook here: Running Remote Playbook
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Get the Full Playbook
This playbook goes beyond documentation—it’s your complete guide to mastering remote team leadership. Other chapters include:
- Running Company-Wide Retreats – Learn how to plan impactful team retreats, from ideal frequencies to strategies for maintaining customer support while your entire team is off-site.
- Mastering Asynchronous Communication – Discover how to hire for async success, implement effective communication practices, and measure collaboration effectiveness.
- Effective All-Hands Meetings – Find out how to make all-hands meetings engaging, with insights on agenda setting, frequency, and participation tools.
- Remote Onboarding Done Right – Explore best practices for seamless onboarding, integrating culture, and using the right tools to facilitate smooth transitions.
