Helen Lee Kupp - Experimentation to Co-create High-Tech Human-centric Flexible Systems

Helen Lee Kupp is Founder and CEO of Women Defining AI and co-author of best-selling book “How the Future Works: Leading Flexible Teams to do the Best Work of Their Lives". She discusses her experiences as a strategy and operations leader benefiting from collaborative experimentation and elevating use cases when exploring AI and other technologies for business and workplace transformation. From her tenure at Slack, Helen emphasizes data fluency and intuitive decision-making, defining and applying metrics, and implementing flexible systems. Her insights offer guidance for navigating AI adoption, hybrid work, and creating flexible human-centric frameworks that empower people and processes.   TAKEAWAYS [02:21] Helen interest in chemistry and bioengineering prompts her to study chemical engineering. [03:43] Helen loves to pair biology’s organic messiness with engineering and systems thinking. [04:36] Reflecting on a non-linear career path guided by attraction to ambiguous problems. [06:17] Helen’s desire for real-world impact leads her from lab work to consulting then startups. [08:07] Joining Slack early, Helen drives innovation projects, expanding as a consumer product. [09:30] The challenge of using data effectively, needing shared definitions across teams. [11:01] How leaders must foster data fluency to enhance decision-making processes. [11:50] Building operational intuition to make decisions using data and metrics in context. [14:05] Flexibility is integral for organizational systems to adapt to changing market conditions. [15:52] A ‘bridge’ describes a balanced need for stable data infrastructures for specific metrics and flexible systems for evolving demands. [18:19] An innovative process to elevate metrics from team insights to company-wide KPIs. [20:28] Hybrid data approaches enable both innovation and operational consistency. [22:36] Slack’s approach to dynamic work systems shapes Helen’s understanding of agile leadership. [24:02] How workplace tech evolves impacting team collaboration and decision rhythms. [26:15] Helen is an early Slack user and comfortable and effective async worker as an introvert. [29:17] ‘How the Future Works’ enabled the authors to share personal experiences and codify the redesigning of work. [32:24] Helen’s consulting trained her about team protocols enabling effective teamwork. [34:36] How personal work preferences are supported by team agreements. [37:55] Helen is prompted to actively define AI inclusively not stumble into it. [38:58] Women Defining AI launches serendipitously to craft AI development and adoption. [43:18] A community of experimentation, Helen approaches the future with a flexible mindset. [45:01] The importance of building intuition for using AI—it’s just as messy as humans! [45:01] IMMEDIATE ACTION TIP: Embrace discovery mindsets and start small by piloting AI in manageable areas of your work, ensuring hands-on practice and learning opportunities for your teams to explore its potential impact.     RESOURCES   Helen Lee Kupp on LinkedIn Women Defining AI Almost Technical Helen’s book “How the Future Works: Leading Flexible Teams to do the Best Work of Their Lives”     QUOTES   “We have a chance to redesign it all right. To redesign not just how we operate together, but to be thoughtful about how different everyone is and bring all that into the redesign.”   “People are looking for structured guidance. They’re not looking for all the answers. But they’re looking for at least that you are thinking through it and that they can try.”   “Experimenting and piloting use cases with individuals and teams to see what works for them and finding ways to elevate that across the broader organization and share practices. The more you can do that, the faster you’ll learn.”   "I appreciate the consulting training because we had to come together in teams so frequently with new teams and new managers. We needed a process around how do we understand how we operate, which may be different than your last team. How do we communicate best and how do we ensure we solicit the best of everyone in this group?"