AI Readiness Starts with Documentation: Lessons from Remote Work

If you’re out there being told to slap AI tools onto everything and call it “digital transformation,” this episode is your reality check. I sat down with Darren Murph—yes, the remote‑work oracle behind GitLab’s all‑remote strategy—to pull back the curtain on what needs to exist before you ever type “chatbot” or “LLM integration” into your roadmap.

We dug into why good documentation isn’t optional anymore, why remote‑work lessons are now directly relevant to AI adoption, and how companies who rushed ahead without building infrastructure are setting themselves up for a trust disaster. In short: if your data, your knowledge systems, your culture aren’t ready for AI, this technology is not your solution—it’s your liability.

What You’ll Learn:
Why knowledge infrastructure matters more than tools when you’re layering AI onto an organization.
How the fundamentals of remote work (async workflows, transparency, writing culture) set the stage for good AI adoption.
The human dimensions of this transition—how to lead teams who feel threatened, how to align incentives, and how to govern innovation without killing it.
What “culture in a distributed world” actually looks like when you’re also bringing AI into the mix—not as HR fluff, but as operational truth.

Key Takeaways:
Documentation ≈ trust capital. If your team pulls up an AI tool only to hit bad or misleading data repeatedly, you’ve just eroded trust—not just in the tech, but in management. As Darren says: “If AI leads you astray four or five times in a row… you’re going to be much less trusting of that technology.”
Remote work = writing culture. The shift to asynchronous workflows over the past few years wasn’t just about Zoom fatigue—it trained companies in self‑service knowledge, clear docs, and distributed decision‑making. Those habits map directly into what AI adoption demands.
Top down + bottom up both matter. You need vision and governance for AI (where are we going, what are we trying to achieve) and incentives and infrastructure that let people play and experiment. If you only have mandates and no permission to experiment, you’ll get compliance, not creativity.
Incentives still matter. Changing the “what you get rewarded for” is essential. If you tell a team: “Use AI to save 20% time,” but you reward them for hours logged or face‑time in the office, things don’t change—they just adopt a new tool without behavior change.
Hybrid or remote, you’re distributed. Whether you’re entirely remote, hybrid, or office‑based—if you’re using AI and modern workflows, you’re effectively distributed. The patterns carry over: async, documentation, transparency.
Humanity isn’t optional. With AI taking over polished, routine work, the human stuff becomes more visible: improvisation, empathy, culture. Encourage your people to bring their full selves — and your systems to reflect that.
Governance = two cords, not one. The best companies aren’t either “free for all” or “AI command‑centre locked down”. They define a shared vision (we’re going here) and let people roam within it. That gives you boundary and freedom both.

Chapters:
0:00 Intro & question: What foundational work do organizations need before layering AI?
2:10 Darren: Many organizations rush to layer AI over what they currently have; they should step back.
4:49 Discussion: How documentation hygiene is essential for trust in AI.
6:54 Assessment: How ready are most organizations for this shift?
9:08 Lessons from remote work that carry into AI adoption: transparency & async.
12:02 Why AI reinforces the need for distributed‑friendly practices.
14:22 Teams’ fear of AI: How to guide them through the transition.
16:07 Incentives and operationalizing AI gains: Profit‑sharing, hackathons, dedicated teams.
18:12 Governance: Balancing creativity and guardrails in AI use.
21:18 Purpose, clarity & structure: Why they matter now more than ever.
22:53 Culture in an AI‑driven remote workplace: Embracing humanity outside work and letting it back in.
25:04 Outro & final thoughts.

Meet Our Guest:
Darren Murph is a globally recognized Future of Work Architect, consultant, speaker, and author, celebrated as an “oracle of remote work” by CNBC and featured among Forbes’ Future of Work 50 for his trail-blazing contributions to distributed work and organizational design. Drawing on 15+ years of experience leading remote and hybrid teams, Darren co-authored the GitLab Remote Playbook and guides companies in building high-performance, resilience-driven operations through inclusivity, asynchronous workflows, and strategic communication.

Learn more: https://peoplemanagingpeople.com/peop...