Promptly Speaking

What if AI could make your employees feel more valued, not less? Jason Stover, Executive Vice President at SSA Group and the builder behind Scout — SSA's internal AI platform — joins Sara and Dan to share how a people-first philosophy is driving one of the most thoughtful AI adoption strategies in the hospitality industry. From getting laid off teams through COVID, to discovering ChatGPT and not s...

What if you could build your company's next internal tool in a weekend, for $30? Aaron Trockman is a partner manager at Glean who had zero formal coding experience — and then built PartnerSync, a fully functional partner automation platform used daily across his sales organization, in about 10 hours using AI tools. In this episode, Sara and Dan sit down with Aaron to unpack exactly how he did it,...

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!!

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 b...

Everyone's been talking about AI this year. Where does it move the needle? Where does it fall short? In the final Promptly Speaking episode of 2025, Sara and Dan take a moment to reflect on what they've learned from their guests, and through their own experimentation with AI in life & work. Now, more than ever, it's important that we stop and take a moment to think about where we're trying to...

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, n...

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...

In this episode of Promptly Speaking , Sara and Dan sit down with Neil Shepherd — a Silicon Valley engineer, entrepreneur, and former leader at PayPal, Scale AI, Cohere, and Play.ai — for a direct, deeply informed look at the AI disruption already unfolding. Neil breaks down why this wave of technology is unlike any before it, why white-collar roles are more exposed than people think, and why the...

What happens to creativity when anyone can generate “good enough” writing in seconds? And how do you keep your voice — your taste — when machines want to average everything out? In this episode, Sara and Dan sit down with Simone Stolzoff — author of The Good Enough Job and the upcoming How to Not Know — to talk about the real skills we need in an age of nonstop change: uncertainty tolerance, ident...

How do we raise emotionally healthy kids in a world where AI companions, chatbots, and digital identities show up earlier than ever? In this episode of Promptly Speaking , Sara and Dan sit down with Sara Filipčić, a researcher, founder of Be Human(e), and expert in childhood social–emotional development. Her work spans the Yale Center for Emotional Intelligence, EdTech innovation, and early field...

Are AI companions making us more lonely? In this episode of Promptly Speaking , Sara and Dan explore how AI is reshaping not only how we think - but how we feel. From chatbots like Replika and Character. AI to Instagram’s synthetic influencers, they unpack what happens when emotional AI starts filling our social gaps - and what we lose when simulated empathy replaces real human friction. This epis...

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...

Are we getting dumber because of AI? 🤖 In this episode of Promptly Speaking , hosts Sara and Dan Roberts explore how generative AI tools like ChatGPT are rewiring our brains. Drawing on new research from MIT, Science Advances, and Harvard Business Review, they unpack how these tools influence creativity, focus, and intrinsic motivation. You’ll hear how AI can raise productivity while lowering ori...

Welcome to the inaugural episode of Promptly Speaking , where hosts Sara and Dan Roberts delve into how AI is transforming our lives. In this episode, they discuss why they started the podcast, their personal backgrounds in tech, and their aim to demystify AI for the everyday person. With insights from various industries and a focus on the human-AI partnership, they seek to provide practical advic...

In this guest episode of Promptly Speaking, hosts Sara and Dan Roberts dive deep into the transformative world of AI with guest Tiago Forte, a renowned entrepreneur and best-selling author. Listen as Forte debunks common misconceptions about AI, reveals surprising industry applications, and outlines how AI can act as a thought partner rather than a simple task automator. From cutting-edge projects...

We talk a lot about what AI can do — but how often do we stop to ask how it thinks? In this episode of Promptly Speaking , Sara and Dan build on insights from their conversation with Tiago Forte to explore how context-aware AI is reshaping the way we think, work, and create. They break down the difference between deterministic and non-deterministic systems — and why that subtle distinction defines...

What happens when a data analyst turns a viral moment into a full-blown business? In this episode of Promptly Speaking , Sara and Dan sit down with Jess Ramos — data analyst turned entrepreneur and one of LinkedIn’s most influential voices, with nearly half a million followers. Jess shares how one viral post changed the course of her career, why she believes everyone should understand data, and ho...

Real people. Real stories. Real AI. Promptly Speaking dives into how artificial intelligence is reshaping the way we live, work, and think, one human story at a time. Meet Sara & Dan Roberts — Sara’s an entrepreneur who’s helped scale some of Silicon Valley’s hottest startups. Dan’s a tech sales leader at Glean, where he talks every day with companies figuring out how to bring AI into their bu...