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Engineering Serendipity: How Community Drives Innovation Featuring Roland Harwood, Milestone Systems What if the most valuable outcomes of a community are the ones you never planned for? In this conversation, Roland Harwood shares insights from over 20 years of building communities and innovation ecosystems, exploring how organizations can intentionally create opportunities for unexpected connections, collaboration, and product innovation. Drawing on his experiences with LEGO Ideas, Milestone Systems' Hafnia community, and the Climate Tech Supercluster, Roland demonstrates how communities can become powerful engines for innovation when people have the space, trust, and tools to contribute. Key Takeaways Create the conditions for serendipity. Stay curious, notice unexpected connections, and make room for ideas that weren't part of the original plan. Build relationships before you need them. Strong communities grow through consistent investment in trust, generosity, and authentic connections. Turn community ideas into innovation. From LEGO's community-driven products to Milestone's developer hackathons, giving members opportunities to create can uncover entirely new possibilities. Measure more than engagement. Beyond attendance, posts, and participation, look for members helping one another, forming relationships, and creating value independently. Be patient and take action. Meaningful communities develop gradually, but acting on emerging opportunities can lead to breakthrough results. The big takeaway: Community isn't just about bringing people together. It's about creating an environment where unexpected connections lead to meaningful outcomes, stronger relationships, and innovation.
# Format: Event Recaps
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In this session with Helen Miller, founder of The Course Edit, explored why engagement drops in learning programs and communities, and how to identify the real causes before jumping to solutions. Helen introduced four dimensions of engagement that help us understand what's happening beneath the surface: Behavioral Engagement: Are people showing up, participating, and completing activities? These visible behaviors are useful signals, but don't always tell us why engagement is changing. Cognitive Engagement: Are learners understanding and applying what they've learned? A drop in participation may indicate that the content is too challenging or that learners need more support. Emotional Engagement: Does the experience feel relevant, valuable, and psychologically safe? People are more likely to engage when they understand why something matters and feel comfortable asking questions or making mistakes. Agentic Engagement: Do learners have opportunities to contribute, make decisions, and take ownership of their experience? Key Takeaways 1. Engagement drops are signals, not diagnoses. Before adding reminders or changing content, investigate what's actually preventing people from participating. 2. Design for learning, not just completion. Helen shared an example where course completion dropped because learners were being asked to apply skills they hadn't been adequately prepared for. The solution wasn't to make the assignment easier, but to provide better guidance and practical examples. 3. Connect engagement to meaningful outcomes. Completion rates tell only part of the story. Look at whether learners can apply their knowledge, change behaviors, and achieve the intended goals. 4. Investigate before you intervene. Follow a simple process: observe behavior, investigate the four dimensions, identify a likely root cause, and design a targeted improvement. The biggest takeaway: Improving engagement isn't about getting people to do more. It's about understanding what they need to succeed and creating experiences that help them get there.
# Format: Event Recaps
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See how Hillarie Ralston from Ironclad turned customer events into engines for product feedback, early access, and loyalty by bringing product teams into the experience.
# Format: Event Recaps
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# Customer Success & Support
# Format: Playbooks
# Gradual: How-Tos
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# Customer Success & Support
# Community
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Learn how to build a community measurement framework that connects community activity to business outcomes, supports budget conversations, and gives finance a clearer view of impact.
# Community
# GTM Strategy
# Format: Playbooks
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Learn how to define what community is meant to influence, align programs to business goals, and help stakeholders understand where community creates value.
# Community
# GTM Strategy
# Format: Playbooks
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A recap of our Context First conversation with Hillarie Ralston on how product-led customer events turn attendee feedback into loyalty, advocacy, and real product impact.
# Community
# Format: Event Recaps
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Richard Millington
Joshua Zerkel
Richard Millington & Joshua Zerkel · Aug 11th, 2026
AI is changing customer expectations. Learn how to connect community, support, and education into one experience that helps customers learn and succeed.
# Format: Event Recaps
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Joshua Zerkel
Richard Millington
Joshua Zerkel & Richard Millington · Aug 11th, 2026
Richard Millington of FeverBee joins Context First to explain why community engagement is declining industry-wide, and which types of knowledge community still creates better than AI or documentation.
# AI
# Community
# Format: Event Recaps
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