In a recent LinkedIn post, John Cutler addresses a frequently asked question regarding the initiation of “OS discovery” and related playbooks. Cutler, a recognized voice in product development and strategy, shared his thoughts on how organizations can effectively begin this often complex process.
Navigating the ‘Where to Start?’ Dilemma
A central theme in Cutler’s post revolves around the common hurdle of knowing where to begin with OS discovery. He highlights that this question is a significant point of interest for many professionals engaging with his work and playbooks. To tackle this, Cutler announced an upcoming hour-long session dedicated to discussing these challenges and sharing practical approaches.
“One of the biggest questions is ‘Where do we start?'”
This direct quote underscores the practical, real-world challenges that leaders face when implementing new discovery frameworks. Cutler positions himself as a facilitator, aiming to provide guidance based on his observations across various companies.
Sharing Best Practices and Fostering Community Input
Cutler’s approach emphasizes a collaborative learning environment. He intends to share strategies that have proven effective in different organizational contexts. However, he also stresses the importance of collective wisdom.
As John Cutler notes, the session isn’t just about him imparting knowledge; it’s also about learning from others. He explicitly states his intention to “most importantly hear what others think!” This inclusive strategy acknowledges that effective discovery practices are often context-dependent and benefit from diverse perspectives.
The Value of Playbooks and Expert Guidance
The post also references a specific playbook related to OS discovery, providing a tangible resource for those seeking to deepen their understanding. The availability of such resources, coupled with opportunities for direct engagement like the announced chat, is crucial for driving adoption and success in complex areas like OS discovery.
“I’ve been getting so many interesting questions about ‘os discovery’, and parts of this playbook.”
This sentiment, as expressed by Cutler, indicates a strong demand for structured guidance in this domain. By offering dedicated time for Q&A and sharing insights, Cutler aims to demystify the process and empower practitioners.
Looking Ahead: Collaborative Discovery
Cutler’s initiative to host an open discussion signals a commitment to continuous improvement and shared learning within the product and business strategy communities. The underlying message is that while starting points can be challenging, a combination of expert guidance, practical resources, and community interaction can pave the way for successful OS discovery implementation.
“Setting aside an hour chat in two weeks for anyone interested.”
This forward-looking statement from Cutler invites participation and collaboration, reinforcing the idea that tackling complex business challenges is often a collective effort. His posts consistently aim to provide actionable advice and foster dialogue among professionals.
📝 About This Content
This article is based on insights shared by John Cutler on LinkedIn.
📅 Originally posted on January 8, 2026 | View original post on LinkedIn →