This Moment We're In

Cindy Chastain
  • 5.0 (7)
  • Business
  • Updated Monthly

This Moment We’re In explores how AI is reshaping how work gets done—from collaboration and decision-making to improving products, services, and operations. Hosted by Experience Innovation and Design leader Cindy Chastain, the show features business leaders sharing real-world experiments and hard-earned lessons from integrating AI into everyday work—the messy middle where change is real, answers are incomplete, and leadership is evolving in real time.

Episodes

  1. Jul 21

    Redesigning Leadership Practices | Martin Granstrom

    As AI makes it easier for anyone to build prototypes, generate ideas, and create artifacts, a new leadership challenge is emerging: how do you help organizations maintain quality, make better decisions, and learn together when execution is no longer the primary constraint? In this episode, Cindy talks with Martin Granstrom, VP of Design at Shipt, about what leadership looks like when production time is shrinking and more is expected for less. Through two practical examples: Martin shares how he's redesigning leadership practices—building systems that help teams scale judgment, improve decision-making, and create better outcomes in an era where everyone can build. Together they explore why the future of leadership may depend less on directing work and more on designing the conditions under which great work happens. Key takeaways: Leadership is becoming the design of organizational practices. As AI changes how work gets done, leaders increasingly create the systems, rituals, and ways of working that help teams consistently produce better outcomes. Learning is becoming visible. The strongest leaders no longer feel compelled to have all the answers. By experimenting openly, sharing what they're learning, and inviting others into the process. Better decisions come from shared creation. When leaders and teams build, prototype, and explore ideas together, alignment happens much earlier. Leadership is shifting from directing work to enabling better work. Leaders increasingly create the conditions that allow individuals and teams to do their best thinking, make stronger decisions, and continuously improve. Curiosity is becoming a leadership capability. In a period of rapid change, leaders who remain curious, experiment actively, and invite others to learn alongside them will adapt more effectively than those who wait for certainty. Chapters 00:00 Navigating AI-Driven Change in Teams 01:23 Shipped's AI Journey and Ecosystem 03:48 The Shift in Design Leadership 06:11 Scaling Judgment in Design 08:59 Creating Tools for Judgment 10:00 Hands-On Leadership in Design 12:38 Building Trust Through Vulnerability 13:03 Democratizing Design and Innovation 14:16 Enabling Leadership Through AI 20:37 Creating Conditions for Collaborative Decision-Making 24:32 Collaborative Decision-Making in Design 28:26 Scaling Collaborative Workshops 32:06 Empathy and Leadership 36:16 The Evolving Role of Leaders 39:30 Design Thinking Beyond Product 42:05 Curiosity and Adaptability in Leadership 47:23 Architectural Leadership in the Age of AI About Martin Granstrom As VP of Design at Shipt, Martin leads a 40-person Product Design and Research organization responsible for the end-to-end digital design ecosystem, spanning member, shopper, and partner experiences, as well as the internal tools that power them. At Shipt, his goal is to build a design-led culture of experimentation and innovation, where empathy, creativity, and business strategy come together to define the future of local commerce. Before joining Shipt, Martin served as VP of Product Design and Research at Sam's Club (Walmart Inc.), where I built and scaled a 120-person global design organization behind award-winning experiences such as Scan & Go, Clubhouse, and the Re:Imagine Retail conference. Over the past two decades, he led design and strategy initiatives across industries such as consumer electronics, retail, and digital platforms, for brands like Samsung, Sony Mobile, and NOOK Media. His leadership philosophy is rooted in empathy-based creative collaboration, empowering teams with permission to play and permission to fail, while maintaining an unwavering focus on user value, business outcomes, and innovation at scale. Music by Kid Kodi Blue Dot Sessions

  2. Jun 10

    Coherence: The Good Bottleneck | Thu Do

    As AI lowers the cost of execution, organizations face a new challenge: deciding what deserves to be built in the first place. In this episode of This Moment We’re In, Cindy Chastain talks with Thu Do, a product builder, strategist, designer, founder, and systems thinker whose career has never fit neatly into a single category. Together, they explore what happens when AI begins to blur traditional boundaries between disciplines and democratize the ability to build. At the center of the conversation is an idea Thu calls coherence: a shared understanding of what is actually true about a product, service, customer, or business at a given moment in time. Thu argues that as execution becomes easier, coherence becomes more important—and that organizations that fail to maintain it risk accelerating in the wrong direction. They discuss:  Why AI is challenging traditional divisions of labor and expertise The rise of “X-shaped” people who connect knowledge across disciplines The importance of shared product coherence, what it means, and why it enables decision quality as more people gain the ability to build Why coherence and more time spend on shaping and de-risking reduces costs Why coherence may become a competitive advantage in an AI-driven world This conversation is ultimately about more than product development. It’s about what kinds of people, teams, and ways of working help organizations make sense of complexity when AI-supported building capabilities become more distributed. Chapters 00:00 Introduction to Thu Do 02:21 The Outsider Advantage 04:41 The Concept of the X-Shaped Person 09:51 The Importance of Coherence in Fast-Paced Environments 12:29 Breaking Down Coherence: Real-World Examples 22:40 The Challenge of Democratization 25:42 Managing Coherence Within Teams 35:01 Understanding the Shared Brain Concept 37:01 Shaping vs. Execution in Product Development 45:59 The Role of Connectors in Teams 47:11 What Leaders Should Take Away 48:47 The Value of Human Work in an AI World 56:15 Closing Reflection About Thu Do Thu Do is a 0→1 AI product leader and founder translating emerging AI research into products people actually use. She moves from concept to production through rapid prototyping, iteration, and scale—defining product direction, establishing technical patterns, and building conviction across cross-functional teams. Thu designs elegant solutions to complex problems, creating experiences that drive real user value in startup environments. She has contributed to $100M+ in fundraising and shipped products serving millions of users, including 1.6M+ multilingual community college students and impact-driven platforms across EdTech, ClimateTech, and HealthTech. Her expertise spans design (BFA, Savannah College of Art and Design), strategy (MA, Indiana University), product management, and GTM startups. She has taught at MICA's Master's in UX Program, Flatiron School, and CUNY, and mentored at various incubators and startup communities. Thu founded TAILORU Collective, helping impact-driven startups move from AI experimentation to AI-native operations and career transitioners upskill via TAILORU Stitch communities. As a founder, her own ventures have spanned industries—from TAILOAR (AR fit tech, patent-holder) to emerging market experiences and now consulting with 20+ innovation teams and counting. She's passionate about creating equal opportunities in underserved markets and building sustainable ecosystems. A global citizen at heart, Thu thrives connecting with people across cultures. She's a vintage lamp restorer, musician, stamp collector, road tripper, and above all, a flawed but unique human. #FutureOfWork #HumanCenteredAI #AIInnovation #ProductDevelopment #LeadershipInAI #OrganizationalChange Kid Kodi by Blue Dot Sessions

  3. May 8

    When AI Changes How Teams Think | Greg Petroff

    In this episode of This Moment We’re In, Cindy Chastain talks with design and innovation executive Greg Petroff about what happens when AI stops functioning merely as a productivity tool and starts reshaping how teams think. Drawing from his work with product organizations navigating AI adoption in real time, Greg shares two contrasting stories: one where AI accelerates an existing product development process, and another where AI begins transforming how teams explore ideas, collaborate, and make decisions together. The conversation explores: The shift from “thinking to make” toward “making to think” Why discernment still matters in an AI-driven workflow The collapsing boundaries between design, product, and engineering AI as a medium for strategic exploration How leadership, roles, and product development models may evolve as these tools mature Rather than focusing on hype or predictions, this episode examines the deeper organizational implications emerging underneath the tooling itself — and why changes in thinking may ultimately reshape the structures around them. Chapters 00:00 Introducing the episode 01:34 Welcome 03:08 Act I - The Bolt on Moment 04:48 Assessing Design Team Maturity 06:16 Navigating AI Adoption in Design 08:14 The Role of Product Managers in Design 16:04 Act II - Improvising toward new value 20:06 The Evolution of Design Processes with AI 28:54 Act III - AI as Velocity Driver vs. Thinking Tool 32:25 Making to Think vs. Thinking to Make 35:51 Act IV - Putting it Into Practice 50:32 Act V - Closing Takeaways 57:03 Reflection About Greg Petroff For over 25 years, Greg been at the forefront of design innovation, crafting user-centric solutions that transform how enterprises and organizations operate across diverse industries. My passion lies in creating products and services that not only enhance security and efficiency but also delight users with their intuitiveness and creativity. As a leader in user experience (UX) and context-first design, he’s had the privilege of shaping digital experiences at some of the world's most innovative companies, including SAP, GE Digital, Google, ServiceNow, Compass, and Cisco. In each role, he’s led design teams that pushed the boundaries of what's possible in digital interactions, always with a focus on solving real-world problems. His approach combines deep user research with creative direction to deliver solutions that truly resonate with end-users. I believe that great design goes beyond aesthetics—it's about understanding context, anticipating needs, and creating seamless experiences that feel natural and effortless. Beyond his corporate roles, he is deeply committed to advancing the field of design. As a founding board member of the Interaction Design Association and chair of the Interaction09 Conference, I've worked to foster community and share knowledge within our industry. He’s also a frequent public speaker, sharing insights on the transformative power of design in organizational strategy and culture. LinkedIn https://www.linkedin.com/in/gpetroff/ AI consultancy: https://unfinishe.com/ Substack: https://gregpetroff.substack.com/ #ArtificialIntelligence #ProductDevelopment #DesignLeadership #Innovation #ProductManagement #AI

  4. Mar 30

    Building Piper Morgan: A Product Management Experiment in Agentic AI | Christian Crumlish

    Cindy talks with Christian Crumlish, product leader and author Product Management for UX People, about his journey building a product management assistant called Piper Morgan. What began as a practical experiment quickly exposed something deeper: how systems drift without structure, and why Agentic AI doesn’t work without trust, governance, and human discernment. At its core, this is a story about what it takes to build with AI—without losing the human. What was revealed What it actually means to create an agent that behaves more like a colleague than a toolWhat an agent learning process looks like in practice—not theoryWhy you can’t shortcut your way to enterprise-ready softwareHow building trust with an agent mirrors how we build trust with peopleWhy agentic workflows push humans up the stack—into strategy, decision-making, and accountabilityWhy existing processes have to be redesigned, not just automated Chapters Act I – The life change and genesis of an idea 1:44 Landing a new role after the 18F layoffs 7:29 The idea: an agent as a teammate, not atool   Act II — TheFirst Build 14:28 Buildingthe initial prototype 15:40 Earlysignals—and early misconceptions 16:22 When the system gets it wrong   Act III – Coding mania and eventual drift 20:24 Starting over 22:10 Leaving product discipline behind 23:28 When speed creates drift   Act IV — The Big Reset 25:55 Governance steps in 28:08 Re-architecting the system 31:25 Teaching the agent how to work with its human 33:36 Building trust between human and machine 39:36 What remains when everything accelerates 43:39 The role of the “good bottleneck”   Act V — From Experiment to Viable System 44:24 What organizations can learn from this experiment 47:28 Why workflows must be redesigned—not just automated 48:21  Why experimentation has to be structured, not ad hoc 50:07 How this changes the role of a product leader        About the guest: Christian Crumlish is Director of Product at Kind and was Director of the Product Chapter at the late, lamented 18F--the former US Government digital consultancy. He brings over two decades of experience in UX design, product management, and information architecture to the challenge of building ethical AI systems. At Kind, Christian defines the product practices, leads a project for VA.gov, improving the online experience for veterans seeking reviews of their disability benefits,  and tracking disability benefits reviews, and explores the possibilities of AI enhanced product management practices. At 18F, Christian worked on federal digital services including the launch of ClimateCorps.gov and passport modernization efforts for Consular Affairs at the State Department, learning how to navigate complex stakeholder interests while keeping user needs central. Follow the ongoing progress of Piper Morgan on Medium Contribute to the build or testing of Piper MorganRead Christian's Book: Product Management for UX People View his profile on LinkedIn

  5. Jan 30

    Judgment as Compass in the Age of AI | Brandt Flomer

    In the first episode of This Moment We’re In, host Cindy Chastain sits down with Brandt Flomer to explore a growing—but often overlooked—risk of AI adoption: the erosion of judgment, taste, and learning itself. Drawing from Brandt’s widely read essay “Craft Is Your Only Moat in the Age of AI,” the conversation examines why many organizations are shipping faster but thinking less—and how unchecked AI workflows can quietly bypass the feedback loops that help people develop good judgment. Together, Cindy and Brandt unpack why speed without discernment isn’t productivity, but capability decay at scale. The episode introduces a practical leadership framework—Compass × Flywheel = Impact—to help teams harness AI’s speed and scale without losing the craft that makes work meaningful, differentiated, and valuable. This is a conversation for leaders navigating AI-driven change who want results without sacrificing standards, learning, or humanity. What You’ll Learn in This Episode Why 95% of generative AI pilots fail to show measurable ROI, and what most leaders are missingHow AI can unintentionally short-circuit learning, apprenticeship, and judgmentWhat “craft” really means—and why it applies far beyond design or creative fieldsHow work slop creeps into organizations and quietly erodes productivityWhy leaders must slow down decision-making even as execution speeds up Chapters 00:00 Navigating AI-Driven Change 01:22 The Importance of Craft in AI 07:30 Defining Craft and Its Relevance 12:27 A Real-World Example of AI Integration 16:22 Cognitive Offloading and Its Implications 19:55 Capability Decay at Scale 23:37 Creating Healthy Friction in Workflows 25:25 Navigating Leadership Challenges 26:58 The Role of AI in Creative Processes 30:07 Maintaining Craft in a Fast-Paced Environment 30:07 Framework for Impact: Compass and Flywheel 38:53 Creating Conditions for Healthy Experimentation 44:48 The Unique Human Contribution in the Age of AI 46:35 The Stakes of New Tools 47:24 Craft and Judgment in AI Integration Links to Brandt's articles Craft is Your Only Moat in the Age of AI Three Ways to Ensure AI Multiplies Craft (Instead of Eroding It)

  • 5 Episodes

Ratings & Reviews

5
out of 5
7 Ratings

About

This Moment We’re In explores how AI is reshaping how work gets done—from collaboration and decision-making to improving products, services, and operations. Hosted by Experience Innovation and Design leader Cindy Chastain, the show features business leaders sharing real-world experiments and hard-earned lessons from integrating AI into everyday work—the messy middle where change is real, answers are incomplete, and leadership is evolving in real time.

Information

  • Creator
    Cindy Chastain
  • Years Active
    2026
  • Episodes
    5
  • Rating
    Clean
  • Copyright
    © Cindy Chastain
  • Show Website
    This Moment We're In