Promptly Speaking

Sara & Dan Roberts
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Jan 13, 2026 ‱ 8min

Podcast Update & House Tour

We're taking a short break to upgrade our equipment & set! In this episode, Sara gives a brief tour of their home & recording spaces, highlighting the challenges they've faced and the changes they plan to make. Subscribe so that you don't miss new episodes! Be back soon!!
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Jan 6, 2026 ‱ 42min

How One CIO Is Rethinking Strategy Without Cutting Jobs with Sree Kancharla

AI is changing everything, from how we work to how we learn to how we take care of our families. But is it replacing jobs
 or creating entirely new opportunities?In this episode of Promptly Speaking, Sara and Dan sit down with Sreeveni Kancharla (“Sree”), CIO at SailPoint, to unpack what the AI revolution really means for leaders, employees, and the next generation entering the workforce.Sree brings a rare, grounded perspective from the front lines of enterprise transformation, balancing innovation, governance, productivity, and humanity in a world where AI agents are becoming part of everyday work.💡 Topics We Cover:How AI is reshaping the workforce and where the real opportunities areWhy AI shouldn’t replace people, but amplify themHow leaders should think about productivity, governance, and strategyWhy junior employees still matter in an AI-driven worldHow AI can support personal life decisions, learning, and creativityThe importance of human judgment, critical thinking, and boundariesWhy embracing AI is no longer optional, but blind trust is dangerous⏱ Timestamps:00:00 AI, Job Displacement, and Opportunity00:43 Introducing Sree and Her Role as CIO02:01 Why AI Is Different From Past Tech Revolutions02:41 The Pressure on Leaders to Define AI Strategy04:39 Junior Roles, Internships, and the Future Workforce08:09 Why Human-in-the-Loop Still Matters15:20 Using AI in Personal Life: Healthcare, Family, and Trust18:20 AI as a Creative and Learning Tool24:38 How AI Empowers the Next Generation26:50 Rethinking Business Processes with AI Agents31:51 Productivity, Strategic Thinking, and Leadership Time36:49 Learning Habits, Curiosity, and Staying Relevant39:08 Final Advice: How to Start Embracing AI TodayHow to Find Sree:LinkedIn: https://www.linkedin.com/in/sreeveni-kancharla/Follow Sara & Dan:Sara: https://www.linkedin.com/in/saralynneroberts/Dan: https://www.linkedin.com/in/danroberts27/Email: hello@promptlyspeakingpod.com
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Dec 30, 2025 ‱ 33min

Using AI to Be More Human (Year in Review)

Sara and Dan explore the impact of AI on daily life and work. They advocate for using AI as a daily tool and highlight the importance of continuous learning. Emphasizing the need to identify real problems before applying AI, they discuss how to optimize business processes and workflow. With real-world applications, they illustrate how AI can improve presence by handling mundane tasks. The duo encourages creative experimentation with AI and reflects on their journey of learning together.
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Dec 23, 2025 ‱ 56min

AI in Sales: Slowing Down to Get it Right with Scott Barghaan

What if the biggest risk in AI adoption isn’t falling behind, but moving too fast without clarity?In this episode of Promptly Speaking, Sara and Dan speak with Scott Barghaan, a longtime enterprise sales leader whose career spans EMC and Salesforce, and who now teaches future business leaders at the Kellogg School of Management. Scott unpacks how AI is actually reshaping the practice of sales, not through flashy tools or automated outreach, but through better preparation, deeper customer context, and higher expectations for judgment. He explains how executives are often pressured to adopt AI before clearly defining the problem they are trying to solve, and why AI delivers real value only when it is applied to concrete constraints around scale, cost, and margin rather than introduced as a solution in search of a use case. The conversation explores how buyers are showing up differently, how great sellers adapt without losing authenticity, and what practical, grounded AI adoption looks like for teams of any size.💡 Topics We Cover:- Why buyers now enter sales conversations later, more informed, and more skeptical- Board-level pressure to adopt AI and how it shapes executive decision-making- Why starting with tools instead of problems leads to disappointment- Using AI to prepare for better conversations, not replace sellers- Customer context as the real advantage in modern sales- Where AI genuinely helps sales teams today and where it can backfire- The risk of AI-assisted communication sounding polished but hollow- Buying committees, political capital, and why “helping buyers buy” matters more than ever- How small teams can pilot AI, measure impact, and scale responsibly- Teaching sales and leadership during a major technology shift⏱ Timestamps:00:00 Introduction to AI, sales, and executive pressure01:04 Scott’s career journey from enterprise sales to academia02:41 Advising AI startups and supporting non-profits04:49 Customer-centric selling in the AI era08:42 How the role of the salesperson is changing11:16 Leveraging AI for research, preparation, and insight25:28 Why buying is harder than selling31:15 Convincing executives to embrace AI thoughtfully33:02 Why this technology shift feels different33:50 AI’s role in business transformation34:29 Challenges and opportunities with AI adoption35:21 What successful AI implementation actually looks like36:42 Addressing fear, risk, and resistance around AI41:03 Lessons from teaching at Kellogg46:03 Final reflections and practical takeawaysHow to Find Scott:LinkedIn: https://www.linkedin.com/in/sbarghaan/Kellogg: https://www.kellogg.northwestern.edu/academics-research/faculty/barghaan-scott/Follow Sara & Dan:Sara: https://www.linkedin.com/in/saralynneroberts/Dan: https://www.linkedin.com/in/danroberts27/Email: hello@promptlyspeakingpod.com
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Dec 16, 2025 ‱ 48min

AI, Misdiagnoses, and the Unsexy Work that Could Fix Healthcare with Matt Crowson, MD

In this episode of Promptly Speaking, Sara and Dan speak with Matt Crowson, a fellowship trained ear surgeon who has spent the last decade working at the intersection of clinical medicine, data, and artificial intelligence. Matt explains why diagnostic error is far more common than most patients realize, using ear infections as a powerful and personal case study. He shares how a machine learning model he co-developed at Mass General achieved roughly 95% accuracy in diagnosing pediatric ear infections, compared to the average human accuracy, which is closer to 60 to 70%, and why that gap matters for both everyday care and global health.The conversation goes beyond diagnostics to focus on where AI is already making meaningful progress in healthcare today, particularly in reducing administrative burden through tools like ambient documentation and message triage. Together, they explore the barriers to AI adoption in healthcare, including privacy, liability, fragmented data systems, and regulation, as well as the growing role of clinicians in shaping AI products.The episode closes with practical advice for patients on how generative AI can be used responsibly right now to better understand medical bills, insurance documents, and care options, while acknowledging the real tradeoffs around data privacy and trust.💡 Topics Covered:Why humans are surprisingly bad at diagnosing common conditionsHow AI can reduce diagnostic variability without replacing cliniciansPediatric ear infections as a global health problemAI in low-resource and rural healthcare settingsAdministrative burnout and “pajama time” for cliniciansAmbient scribes and inbox triage as early AI winsPayers vs providers and how healthcare actually worksAccountability and liability when AI is involved in careWhy healthcare AI moves slower than other industriesHow patients can use generative AI today without over-trusting it⏱ Timestamps:00:00 Introduction to ear infections and AI in healthcare00:44 Meet Matt Crowson: from ENT surgeon to AI advocate01:36 Payers vs providers and how the healthcare system functions02:39 AI and administrative burden in clinical work04:55 Privacy, safety, and regulatory barriers to AI adoption09:37 What a Chief Medical Officer does in an AI company13:37 AI in rural healthcare and pediatric ear infection case study26:35 Accountability and liability in AI-assisted care26:51 The scalpel analogy and human responsibility29:57 AI’s potential impact on healthcare costs30:41 Generative AI and patient empowerment36:10 What the future of AI in healthcare may realistically look like36:40 How AI tools are implemented inside hospitals38:35 Real-world AI deployments and auditing41:14 Vendor and healthcare system partnerships42:01 Practical advice for patients using generative AI45:07 Final reflectionsHow to Find Matt:LinkedIn: https://www.linkedin.com/in/matthewgcrowsonFollow Sara & Dan:Sara: https://www.linkedin.com/in/saralynneroberts/Dan: https://www.linkedin.com/in/danroberts27/Email: ⁠hello@promptlyspeakingpod.com⁠
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Dec 2, 2025 ‱ 46min

The White-Collar Shakeup & How to Stay Ahead with Neil Shepherd

Neil Shepherd, a Silicon Valley engineer and entrepreneur, discusses the unprecedented impact of AI on white-collar jobs and industries. He explains how AI is drastically transforming marketing, legal work, healthcare, and manufacturing by automating tasks and altering career trajectories. Neil introduces the American Dream Index, a data-driven tool aimed at assessing middle-class stability. He emphasizes adaptability, curiosity, and continuous learning as crucial traits for thriving amidst rapid technological change.
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Nov 25, 2025 ‱ 42min

How Great Writers Stay Ahead of AI with Simone Stolzoff

Simone Stolzoff, an author and journalist focusing on work and identity, explores the evolving landscape of creativity in the age of AI. He discusses how to maintain a unique voice amid AI-generated content and the importance of differentiating human judgment in writing. Simone emphasizes using AI strategically, treating it as a developmental tool rather than a replacement. He advocates for embracing uncertainty as a pathway to meaning and encourages listeners to cultivate taste and agency as essential skills for navigating the future.
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Nov 18, 2025 ‱ 51min

Raising Resilient Kids in the Age of AI with Sara Filipčić

Sara Filipčić, a researcher and founder of Be Humane, discusses the impact of AI on children's emotional development. She shares insights on curbing reliance on AI companions and emphasizes the importance of offline connections to build resilience. Sara advises parents on gradually introducing technology and highlights the need for co-viewing apps to foster quality interactions. She also explores cultural differences in human-machine relationships, particularly in Japan, and underscores the power of open communication for nurturing emotionally healthy children.
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Nov 10, 2025 ‱ 21min

When Your Best Friend Is a Bot

Explore the impact of AI companions on loneliness and mental health. Discover how chatbots like Replika can fill emotional gaps, while also examining the risks of replacing real human connections. Learn why feelings of loneliness may not always need fixing and how friction in real friendships fosters deeper bonds. Delve into the difference between empathy and sympathy, and practical ways to use AI for emotional support without losing touch with humanity. This insightful conversation emphasizes the importance of intentional AI use in maintaining genuine relationships.
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Nov 4, 2025 ‱ 53min

A Better Way to Use AI with Dr. Ravit Dotan, PhD

How do we use AI without losing what makes us human?In this episode of Promptly Speaking, hosts Sara and Dan Roberts sit down with Dr. Ravit Dotan, PhD - a practical philosopher and AI ethicist - to unpack the cognitive, ethical, and emotional effects of our growing reliance on AI.💡 You’ll learn:- Why using AI can actually reduce brain engagement - and how to prevent it- How to apply ethical reasoning in everyday AI use- The “Chef Approach” to AI - a framework that keeps humans in control- What skills will matter most in the next decade of AI-driven work🧠 Whether you’re an AI optimist or a cautious skeptic, this episode explores how to stay curious, ethical, and fully awake in the age of intelligent machines.⏱ Timestamps:00:00 – Welcome to Promptly Speaking00:20 – Meet Dr. Ravit Dotan: From philosophy to AI ethics03:50 – The gray zones of AI ethics07:49 – What AI does to your brain16:58 – How to brainstorm *with* AI (not let it think for you)25:16 – Ethical adoption in business30:37 – How to build trust into AI workflows36:12 – The “Chef Approach” explained39:35 – Custom chatbots, agents, and the next frontier45:42 – The skills your brain needs for the future of work51:11 – Final reflectionsDr Ravit Dotan:https://www.linkedin.com/in/ravit-dotan/https://www.techbetter.ai/Follow Sara & Dan:Sara: ⁠https://www.linkedin.com/in/saralynneroberts/⁠Dan: https://www.linkedin.com/in/danroberts27/Email: ⁠hello@promptlyspeakingpod.com

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