What happens when we bring more humanity—and humor—into technology, leadership, and the systems that shape our world? In this episode, discover how we can do good better amidst complexity, disruption, and AI-driven change.

In this episode, Kate O’Neill welcomes author, comic, and advisor Jess Pettitt to explore how imperfect people and organizations can “do good better.” Together, they tackle topics from confronting bias in technology and leadership, to creating cultures where dissent—and learning from failure—are possible. Jess Pettitt shares high-stakes humor and vulnerable stories, unpacking why “good enough now” is sometimes vital and sometimes not enough.

Topics covered:

• Using humor to open up difficult conversations
• The limits of certainty and performance in leadership
• Organizational values and aligning intention with action
• The power of curiosity and the “Prepare, Recognize, Respond” framework
• Navigating positional power and fostering inclusive cultures
• Exposing neutrality and hidden power in technology and policy
• Redefining hope, agency, and responsibility in complex environments
• Generosity and actionable steps for failing together in the right direction

Connect with Jess Pettitt
Website


Episode Chapters:
00:00 Introduction and Welcome
01:19 Guest Introduction: Jess Pettitt and Body of Work
03:19 A Flamingo, Complexity, and Unexpected Human Moments
05:21 Humor’s Role in Difficult Conversations
09:11 Learning, Language, and Avoiding Performative Efforts
12:16 Organizational Values, Shared Goals, and Truth Telling
15:24 Discomfort with Complexity and the Realities of Safety
17:00 Making Room for Dissent and Practicing Curiosity
19:41 Feedback Loops and Real-Time Adjustment
24:08 AI Tools, Accuracy, and Personal Responsibility
26:44 Cultural and Conscious Response vs. Habitual Reaction
29:42 “Good Enough Now”—Progress, Stakes, and Ethics
33:24 Humanity, Everyday Generosity, and Self-Reflection
36:30 Balancing Ego and Humility in Driving Change
39:09 Power, Voice, and Cultural Structures in Organizations
45:25 Recognizing Politics and Power Hiding Behind “Neutrality”
51:59 Imagining a Hopeful, Human-Centered Future
57:32 Reclaiming Coexistence and Forward-Looking Hope
01:01:29 Closing Remarks and Takeaways

How do data science and AI impact social justice, and what happens when massive tech infrastructure lands in local communities?

Assistant professor and author Ben Green joins Kate O’Neill on The Tech Humanist Show to discuss AI, data centers, and how technology impacts social justice, communities, and local governments. Hear insights on responsible data science, community resistance, and sustainable tech.

Topics covered:

• The relationship between data science, AI, and social justice
• Algorithmic Realism and responsible data science methods
• Public resistance and organizing against data center expansion
• Impact of data centers on small towns and local governance
• Environmental justice and the burdens of tech development
• Power grid strain and electricity cost distribution
• The opaque economics and long-term sustainability of data centers
• The role of technologists and communities in shaping technology’s future

Connect with Ben Green
Website
Signup for Algorithmic Realism

Episode Chapters:
00:04 Introduction to The Tech Humanist Show
01:29 Conversation with Ben Green Begins
02:05 Data Science and Social Justice: The Connection and Contradictions
03:49 Algorithmic Realism: Rethinking Responsible Data Science
06:13 Unlearning Optimization: Real Stories from Boston EMS
09:31 Beyond Tech: The “Smart Enough City” Philosophy
10:26 Hype, Policy, and the Expansion of Data Centers
13:49 The Power Imbalance and Role of Public Resistance
16:54 Key Findings from “What Happens When Data Centers Come to Town”
21:36 Land Use, Community Decisions, and Generational Trade-offs
24:55 Environmental Justice & Health: Who Bears the Burden?
28:25 Data Centers, Power Grid Strains, and Electricity Costs
33:17 Hardware, Supply Chain, and the Sustainability of Data Centers
36:41 Heat Generation and Local Climate Effects
38:09 How Community Organizing Shapes Technological Outcomes
42:41 Building a Bridge: Technologists, Communities, and Hope for the Future
46:21 Closing Thoughts and What Gives Hope

Can mission-driven technology and AI truly work hand-in-hand to better serve humanity?

Join Kate O’Neill as she brings The Tech Humanist Show live to the SAFe & AI Summit with a compelling conversation featuring Lindsay Ann Wirthlin, who leads enterprise agile transformation at the American Red Cross.

Lindsay shares powerful stories about weaving technology into mission-driven work when every minute counts. Discover how the American Red Cross uses SAFe patterns and agile practices as the backbone for AI adoption and organizational change.

Topics Covered

• Mission-driven technology at the Red Cross
• The role of SAFe patterns in AI adoption
• Prioritization in high-urgency organizations
• Tackling change and adoption fatigue
• Overcoming the human barriers to AI
• Partnerships between Agile and AI teams
• Measuring business value in technology transformation
• Practical workshops for AI intake and adoption
• Building trust and conflict resolution between teams
• Success stories and the importance of scaffolding
• The core of agile: people and relationships

Connect with Lindsay Ann Wirthlin
The American Red Cross
Lindsay Ann’s Instagram

Connect with Scaled Agile on LinkedIn
SAFe by Scaled Agile, Inc
AI-Native Training by Scaled Agile, Inc.


Episode Chapters
00:04 Introduction and context at the AI Summit
01:13 Mission-driven technology in action
02:17 Technology and the human experience at the Red Cross
03:34 What is SAFe and why it matters for leaders
04:06 Prioritization in urgent, mission-critical settings
05:21 Integrating AI: fears, realities, and professional impact
07:01 Navigating AI and Agile priorities
08:38 Signals & strategies for closing collaboration loops
09:42 Adoption fatigue and the human side of new tech
12:01 Bridging AI and organizational change management
13:17 Agile transformation as scaffolding for AI
15:28 From idea to outcome: real-world application of agile + AI
17:40 Forging practical partnerships between Agile COE and AI
19:11 Team linkages, intake models, and coaching
22:02 Decision-making boundaries and conflict resolution
24:23 Measuring effectiveness across teams
26:10 The AI intake problem-solving workshop
29:03 Lowering the adoption threshold: demos and use cases
32:15 AI coaches and bridging team learning
34:17 Tooling innovations for backlog management
35:55 Practices for Monday: inspect, adapt, and connect
38:04 The heart of transformation: people as scaffolding
39:39 Sources of hope and looking ahead
41:23 Closing remarks & credits


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