135: 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 impa