Asking Good Questions with Edward Roske

Edward Roske
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  • Technology

 In this podcast, we explore the CFO's office's past, present, and future, examining how technology and AI are transforming finance. Join Edward Roske and referents as they discuss innovative ways to enhance the role, optimize processes, and shape the future of financial leadership.  Designed for CFOs and finance leaders, each episode provides actionable insights into leveraging technology to drive growth, improve efficiency, and address challenges. With an engaging tone, the podcast simplifies complex concepts, covering topics like automating tasks, real-time data analysis, and strategic planning. Key themes include the shift from traditional finance methods to innovative, technology-driven processes and real-world examples like scenario modeling and automated reporting. The podcast also highlights future trends, such as generative AI for forecasting and advanced analytics for decision-making, promising to shape financial management. Edward Roske inspires listeners with practical advice and tools to embrace technology confidently. Tune in for strategies to thrive in the evolving financial landscape.

  1. 6d ago

    You Can't Prompt Your Way to a Flying Car | Tim Berglund

    Tim Berglund spent twenty years calling AI a promissory note. Always a bright future, never a bright present. (The field was born overpromising. The Dartmouth crew figured they'd nail human intelligence in a couple of months. That was the 1950s.) Then in December 2025 he opened Claude Code and said it on tape: "Okay, this is real." So I asked him what he sees now that he didn't see in the twenty years he spent calling this a trick. Coding got cheap, and cheap coding exposed the true limiting factor, which is that it's hard to make things that don't suck. His words: coming up with a good idea, still hard. Designing a product interface, still hard. Seven months into the agentic revolution, Jira has not suddenly become good. (Check your own tools and tell me he's wrong.) He's completely sold on the tool and completely unsold on the idea that there's a mind in there. It talks like a mind, but it's not one. We dig into why the first machine that uses language the way we do keeps fooling our theory-of-mind reflex, whether AI is making work better or just faster, what the Turing test is worth now that it's been passed and gotten boring, ELIZA pulling the same trick in 400 lines of code back in the sixties, and why his firmware is still handcrafted, artisanal, small-batch C++ (like making your own furniture out of wood). Also in here: the day Claude Opus started calling the other agents its siblings (that terminology did not come from me), the Postmodernism Generator as 1990s proto-slop, the bicycle being invented after photography, and my air-band machine. I have played Ode to Joy on an air piano. It was not quite as much fun as I thought it would be. (The air drums are just clank, clank, clank.) I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. Tim speaks at the Caribbean AI Summit this October in San Juan, on the real history of AI. He gave me a taste of it in this episode and offered to give me the rest, which I turned down so he'd still have a talk to give. Come find us: CaribbeanSummit.AI LINKS Caribbean AI Summit (Tim speaks, Oct 9-10): https://CaribbeanSummit.AI Tim's site (writing, talks, Substack): https://timberglund.com Tim on X: https://x.com/tlberglund BOOKS & RESEARCH MENTIONED The Dartmouth workshop (the 1950s proposal that kicked off AI as a field) ELIZA, Joseph Weizenbaum's 1960s chatbot (Tim: about 400 lines of code) The Postmodernism Generator (the 90s fake-essay site Tim cites as proto-slop) The Turing test (passed, and passe, per this conversation) The Hitchhiker's Guide to the Galaxy, Douglas Adams (my fault, as usual) Also mentioned: Claude Code, Claude Opus 4.8 and Sonnet 5, Apache KafkaThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  2. Aug 19

    With AI, the Winners Will Be the Small Companies | Juan Carlos Pedreira

    Juan Carlos Pedreira told me about a study from this May: 90% of Puerto Ricans only use ChatGPT. Then he told me the winners of the whole AI era will be the small guys. He'd know: he co-founded the Social Business Hub, a digital consultancy in San Juan, and for 15-plus years he's been dragging traditional media companies (Teleonce, Spanish Broadcasting System, Telecinco, and others) into the digital age, and now the AI one. He advises businesses across Puerto Rico, the Dominican Republic, Costa Rica, and Panama, so he sees who's moving and who's stuck. And right now he's running a project where four people do work that used to take five or ten. We get into the two kinds of workers showing up inside every company: the rogue AI person with all the tools, and the one still feeding the fax machine. His dad's IBM XT makes an appearance, along with the accountant who went from "I lost my job" to all in, which Juan Carlos says is happening again right now at super hyper speed. Also in here: why AI belongs with the CEO instead of the IT department, what happens when 800 or 900 million people get handed a very powerful tool without instructions (his numbers), the client Excel report that took a full day and now takes minutes, and my confession that I've got fourteen agents running right now, and that managing them has somehow become a 24/7 job (they do not sleep, which sounded like a feature when I set them up). His two-year prediction: the gap between small and big gets wider, driven by upstarts completely off the radar. I think we're not far from the first one-person billion-dollar company. At one point I told him I had about 45 follow-up questions and genuinely didn't know which one to ask first. Come see which one I picked. I'm Edward Roske, and this is Asking Good Questions. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. Juan Carlos speaks at the Caribbean AI Summit this October in San Juan. His talk: "AI for Humans: How a Small Business Can Now Out-Compete a Fortune 500 Without Hiring a Single Engineer." Come find us: CaribbeanSummit.AI LINKS Caribbean AI Summit (Juan Carlos speaks, Oct 9-10): https://CaribbeanSummit.AI Social Business Hub (SBH Digital), Juan Carlos's consultancy: https://sbhdigital.com Juan Carlos on LinkedIn: https://www.linkedin.com/in/juancpedreira/ Juan Carlos on X: https://x.com/juancpedreira (on air he calls X his "social media drug") BOOKS & RESEARCH MENTIONED The PR Digital Trends Study 2026 (Estudios Tecnicos + the SME Digital & Innovation Forum, May 2026), the study Juan Carlos cites: https://newsismybusiness.com/puerto-rico-digital-media-use-hits-95-in-2026-study/ "The AI Daily Brief" with Nathaniel Whittemore, the daily AI podcast Edward listens to every day (he blends the name to "the AI Daily Breakdown" on air; this is the real show): https://aidailybrief.ai Anthropic's AI courses (where Juan Carlos points business owners who ask him where to start) Also mentioned: Claude, Claude Code, and Claude Cowork; MCP connectors; QuickBooks; Shopify; LinkedIn Learning; CourseraThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  3. Aug 5

    We're Running an AI Experiment on Our Kids | Bivin Sadler

    We're running an experiment on our kids. And we won't see the results for about 20 years. That's Bivin Sadler. He teaches the data scientists at SMU. He's also the dad of an 8-year-old whose default study partner is now an AI. So which is it? Is Gen AI the best tutor a kid ever had, or the thing that hollows out the ability to think? Bivin says it hangs on whether they learned the first principles first. His fix for keeping students actually learning, from kindergarten through college, is an 800-year-old idea: the oral exam. The problem was always the math. Thirty students at thirty minutes each doesn't fit in a semester. So Bivin built Elenkis, a voice AI that runs a real oral exam for every student (yes, the AI asks the questions now), and finally makes it work for a whole school. We get into "trust, but verify" (the same rule he gives his 8-year-old and AT&T's data scientists, which should tell you something) and the stuff you only ever learned by taking the long way around. Plus what actually gets a new grad hired now, which isn't what you'd guess. Whether you're raising a kid on this stuff or teaching one, stick around for this one. Asking Good Questions is hosted by Edward Roske. New conversations with the people figuring out the human side of AI. If one of these questions stuck with you, subscribe and send it to someone who'd take the other side. Bivin joins Edward on stage at the Caribbean AI Summit this October. Come find us: CaribbeanSummit.AI LINKS Bivin's book, "Time Series for Data Science: Analysis and Forecasting" (CRC Press): https://www.routledge.com/Time-Series-for-Data-Science-Analysis-and-Forecasting/Woodward-Sadler-Robertson/p/book/9780367543891 Elenkis, Bivin's oral-assessment platform: https://elenkis.com Caribbean AI Summit (Bivin speaks, Oct 9-10): https://CaribbeanSummit.AI Bivin Sadler at SMU: https://datascience.smu.edu/about/leadership-and-faculty/bivin-sadler/ Bivin on LinkedIn: https://www.linkedin.com/in/bivin-sadler/ BOOKS & RESEARCH MENTIONED "Time Series for Data Science: Analysis and Forecasting" - Wayne Woodward, Bivin Sadler, and Stephen Robertson (Chapman & Hall/CRC, 2022) UNESCO, "Guidance for generative AI in education and research" (2023) Ethan Mollick, The Wharton School - his approach to students using AI in class Khan Academy - Sal Khan's case for an AI tutor for every student Elenkis - Bivin's platform bringing the oral exam back at scale (elenkis.com) Also mentioned: SMU's M.S. in Data Science program, and the AT&T data-science bootcamp Bivin helped buildThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  4. Jul 22

    Dr. AI Says That for Puerto Rico, AI Is Life and Death | Nesty Delgado

    Nesty Delgado commanded a Puerto Rico National Guard task force through Hurricane Maria. His line about it stopped me cold. "We were making life-and-death decisions back there, with incomplete data." Today, on the island, they call him Dr. AI. I didn't fully see it until we were in the conversation. For Puerto Rico, AI is a matter of life and death. Economic and cultural, yes. And if the next storm finds us as blind as the last one, literal too. What got me most was the order he puts things in. Values and principles at the top, emotional intelligence under that, tools dead last. Software barely makes his list. (I've written ten books trying to explain this stuff without the jargon. Nesty does it on live TV, which feels like cheating.) We get into shadow AI and the company data walking out the door on personal accounts, the clock that just jumped from 40 percent to 65 percent, why he warns his own competitors, and the Caribbean AI Summit he wants ten thousand people to attend. The Caribbean AI Summit is October 9 and 10 in San Juan, and Nesty presents. CaribbeanSummit.AI Asking Good Questions is Season 3: The Human Side of AI, hosted by Edward Roske. New conversations with the people building AI, and the rest of us wrestling with it. Subscribe and you'll catch every one. LINKS Nesty Delgado: NestyDelgado.com Team 1144: team1144.com AblaTek: ablatek.com Caribbean AI Summit: CaribbeanSummit.AI Find Nesty on LinkedIn, Instagram, and Facebook as Nesty Delgado S3:E2This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  5. Jul 16

    Can AI Be Good for Business and Good for Humanity? | Richard Benjamins

    Richard Benjamins's new book, The AI-Driven Company, explains how organizations can move beyond AI hype and experiments to create scalable, tangible economic value. Edward and Richard also discuss whether AI can create both business value and social value, who should lead AI inside a company, and how generative AI may affect human cognition. Richard has spent three decades in AI. He is an author, a leader in responsible AI, co-founder of an AI ethics observatory, and a builder of AI-for-good and cognitive-health initiatives. He led responsible AI at Telefónica, one of the world's largest telecommunications companies; co-founded OdiseIA, an observatory focused on AI's social and ethical impact; and helped create brAIngym, a project focused on cognitive health in the age of generative AI. What's one way AI can be used for good? Tell me in the comments. Asking Good Questions is hosted by Edward Roske. New episode every week this season. Subscribe: https://www.youtube.com/@Roske-AI LINKS Richard's new book, The AI-Driven Company (LID Publishing), is out July 16 in the UK and November 16 in the US. Buy it wherever you get your books, and support your local bookseller if you can. Publisher: https://lidpublishing.com Caribbean AI Summit (Oct 9-10, San Juan): https://CaribbeanSummit.AI Richard Benjamins on LinkedIn: https://www.linkedin.com/in/richard-benjamins-490554/ OdiseIA, the AI ethics observatory he co-founded: https://odiseia.org BOOKS & RESEARCH MENTIONED The AI-Driven Company, Richard Benjamins (LID Publishing, 2026) Gödel, Escher, Bach: An Eternal Golden Braid, Douglas Hofstadter (1979) Crossing the Chasm, Geoffrey Moore (1991) "Your Brain on ChatGPT," MIT Media Lab, Kosmyna et al. (2025) Flowminder Foundation, mobile-phone data for disaster and epidemic response: https://flowminder.org OdiseIA4Good, the social-good arm of OdiseIA: https://odiseia4good.org brAIngym, the OdiseIA project on keeping your mind sharp while AI does the reps for you CHAPTERS 0:00 Cold open: which jobs does your brain still do on its own? 3:13 How long have you actually been doing AI? (three decades in) 4:30 Responsible AI: does it slow you down, or speed you up? 7:36 Ethical AI vs. AI for good: aiming it at what really helps people 10:47 Whose job is the good-but-unprofitable AI: companies, government, or non-profits? 13:07 Aiming AI at disasters: preparedness and the Flowminder story 19:00 Telefonica: turning phone data into social good (and a business) 22:05 From "Chief Electrical Officer" to Chief AI Officer: does the new title actually deliver? 26:57 Who should own AI: the office of the CFO, or IT? 33:45 How does a company cross the chasm to actually being AI-driven? 37:06 The brain gym: what worried you enough to start it? 38:34 Your brain on ChatGPT: what the MIT study found 42:37 Keeping your brain sharp: darts, table tennis, and the APETECE method 46:07 When's the book out, and where to find Richard 48:03 The takeaway: the one job to keep for yourselfThis episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  6. 10/15/2025

    Zain Oke on Surviving a Corporate Crisis — and Selling to Chobani

    In this episode of Asking Good Questions, host Edward Roske sits down with Zain Oke, whose career reads like a masterclass in leadership, resilience, and strategic reinvention. From nearly two decades at Deloitte to the boardroom of Daily Harvest, and now leading automotive operations at AAA Northern California, Zain’s journey is a rare blend of financial discipline, operational innovation, and fearless transformation. The conversation begins with breaking news — Chobani’s acquisition of Daily Harvest — and dives into what it feels like to sit in the room when your company is being bought. Zain shares the inside view of how culture, values, and governance shape such decisions, and how companies can recover trust and rebuild momentum after public crises. They then explore the evolving relationship between AI and corporate oversight: how boards and audit committees should evaluate AI initiatives, separate game-changers from “expensive toys,” and build risk frameworks that keep innovation safe and accountable. Zain reveals how AI isn’t just reducing costs — it’s unlocking new possibilities for startups and scaling teams by lowering barriers to insight and automation. The discussion moves to the automotive future: from electric-vehicle repair pilots to the psychological barriers around autonomous cars. Zain candidly reflects on the balance between safety, public trust, and innovation, reminding listeners that AI’s biggest challenge may be the human fear of losing control. Finally, she offers invaluable advice for finance professionals: how to stay relevant as automation reshapes the CFO’s office, why governance experience is the new gold standard for board readiness, and why learning to “flow through data” is the key skill of the decade. If you care about finance, AI, corporate transformation, or the next wave of board leadership, this conversation will change how you see the intersection of business and technology. 💬 Quotes & Highlights “It’s not what happened — it’s what happens next.” “AI can be a force multiplier, not just a cost reducer.” “Boards don’t need more retired executives; they need active operators.” “Fear of losing control is at the heart of resistance to AI.” “Auditing teaches you how every part of a business actually works.” “Good information in, good information out — that never changes.” “We can’t stop what’s been unleashed, but we can help people trust it.” 🕒 Chapter Breakdown Intro – From Big 4 to Boardrooms (00:00–01:00) Chobani × Daily Harvest Deal (01:00–03:00) Recovering from Crisis & Rebuilding Trust (03:00–05:00) AI in the Boardroom: Guardrails & Governance (05:00–08:00) The Wellness Economy & Big-Brand Acquisitions (08:00–10:00) AI’s Impact on Finance & Operations (10:00–13:30) Digital Transformation in Automotive Services (14:00–17:00) Career Pivot: From Auditor to Operator (20:00–23:00) Balancing Board vs Operator Roles (24:00–26:00) Future of Finance & Automation (27:00–30:00) How to Join a Board (and Stay Relevant) (31:00–34:00) Lightning Round + Final Thoughts (34:00–39:00) This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  7. 10/01/2025

    From Oracle to AI Ops: Kellyn Gorman’s Playbook for Future-Proof Data Teams

    In this episode, Kellyn Gorman joins us for a candid conversation about what AI really means for data leaders, DBAs, and finance teams. From uncovering hidden bias in system defaults to rethinking how humans and AI collaborate, Kellyn lays out a roadmap that is both pragmatic and inspiring. If you’ve ever wondered whether AI will replace your role—or reshape it into something more impactful—this discussion is for you. Listeners will walk away with fresh insight into AI governance, the future of database engineering, and the leadership mindset needed to thrive in a rapidly changing landscape. Top Quotes “AI won’t replace deep specialists—it will demand they evolve.” “Bias doesn’t only exist in people; it’s baked into system defaults.” “Your job isn’t going away—it’s shifting to higher-value decision making.” “If you’re not questioning how your data is being used, you’re already behind.” “AI is a tool. How you lead with it is what creates advantage—or chaos.” Chapters Intro & Kellyn’s Journey — From Oracle DBA to AI thought leader AI Myths vs Reality — What AI changes, what stays the same The Bias Factor — How hidden defaults distort outcomes The Future of Database Work — DBAs, DevOps, and machine collaboration AI Governance — What leaders must prioritize right now Practical Playbook — Steps teams can take to future-proof their data ops Closing Thoughts — Kellyn’s advice to leaders navigating disruption This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

  8. 09/17/2025

    The 4 P's of Finance Excellence: Mark Dendle Reveals His Secret Formula for Business Transformation

    Summary In this engaging conversation, Mark Dendle and Edward Roske explore the evolving landscape of finance, emphasizing the integration of AI, the importance of teamwork, and the common challenges faced across various industries. Mark shares his leadership philosophy, highlighting the significance of diversity and inclusivity in building effective teams. They discuss the critical role of data analytics and technology in driving business decisions and the future of finance as it adapts to new tools and methodologies. Mark's journey through different sectors showcases the transferable skills in finance and the necessity for continuous learning and adaptation in a rapidly changing environment. Takeaways AI is transforming finance, allowing for more efficient processes.Teamwork and diversity are essential for effective leadership.Financial skills are transferable across industries.Data analytics is crucial for informed decision-making.The role of CFO is evolving with technology integration.Continuous learning is necessary for career advancement.Understanding individual motivators is key to team success.Servant leadership fosters a supportive work environment.Project management is vital for successful transformations.Embracing change is essential in the finance sector.titles Navigating the Future of Finance with AIThe Power of Teamwork in Financial LeadershipSound Bites "The power of technology has really helped.""Vive la différence!""Have a great attitude, love learning."Chapters 00:00 The Excitement of AI Agents 05:47 The Philosophy of Teamwork 12:34 Common Financial Challenges Across Industries 22:02 The Four P's of Leadership 30:05 Cultural Influences and Personal Growth 35:42 Diversity of Thought and Paradoxical Thinking 41:01 The Evolution of Finance and AI Integration 49:32 The Future of Finance Careers and Skills This episode of Asking Good Questions is brought to you by Caprus.Ai. Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.

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 In this podcast, we explore the CFO's office's past, present, and future, examining how technology and AI are transforming finance. Join Edward Roske and referents as they discuss innovative ways to enhance the role, optimize processes, and shape the future of financial leadership.  Designed for CFOs and finance leaders, each episode provides actionable insights into leveraging technology to drive growth, improve efficiency, and address challenges. With an engaging tone, the podcast simplifies complex concepts, covering topics like automating tasks, real-time data analysis, and strategic planning. Key themes include the shift from traditional finance methods to innovative, technology-driven processes and real-world examples like scenario modeling and automated reporting. The podcast also highlights future trends, such as generative AI for forecasting and advanced analytics for decision-making, promising to shape financial management. Edward Roske inspires listeners with practical advice and tools to embrace technology confidently. Tune in for strategies to thrive in the evolving financial landscape.

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