Asking Good Questions with Edward Roske

Edward Roske

 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. 4d ago

    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.

  2. 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.

  3. 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.

  4. 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.

  5. 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.

  6. 09/03/2025

    Why Sipei Bowman Says Accountants Have the ‘Highest Pain Tolerance’ in Tech

    In this episode of "Asking Good Questions," host Edward Roske sits down with Sipei Bowman, a trailblazer in the realm of digital transformation within the finance sector. With over two decades of experience, Sipei has been at the forefront of revolutionizing financial systems at Jackson Square Aviation, overseeing assets exceeding $13 billion. Sipei recounts her journey from the early days of relying on Excel spreadsheets to spearheading the implementation of sophisticated ERP systems like Workday and Microsoft Business Central. She shares the challenges and triumphs of transitioning from traditional methods to embracing digital solutions that streamline operations and enhance decision-making processes. Listeners will gain insights into the strategic role of finance in today's fast-paced business environment, where real-time data and AI-driven analytics are becoming essential. Sipei discusses the importance of integrating technology with financial planning and analysis (FP&A) to become a strategic partner in business growth. This episode is a must-listen for finance professionals and business leaders eager to understand the impact of digital transformation on financial operations and the future of AI in finance. Tune in to explore how technology is reshaping the financial landscape and what it means for the future of financial leadership. Episode Highlights: Introduction to Digital Transformation in Finance Sipei Bowman's journey from Excel to ERP systems The role of AI in modern finance Challenges and successes in implementing digital solutions The strategic importance of FP&A in business growth Future trends in finance and technology Chapters: [00:00] Introduction Host Edward Roske introduces the topic and guest, Sipei Bowman. [02:15] Early Days of Finance Sipei shares her experiences starting with Excel and the initial challenges faced. [08:30] Embracing Digital Transformation Discussion on the transition to ERP systems and the impact on financial operations. [15:45] AI and Real-Time Analytics Insights into how AI is reshaping financial decision-making and operations. [22:00] Strategic Role of FP&A Exploring the evolving role of finance as a strategic business partner. [28:30] Future of Finance Predictions and trends for the future of finance and technology integration. [35:00] Conclusion Final thoughts and takeaways from Sipei Bowman. Subscribe to "Asking Good Questions" for more insights on business, technology, and financial leadership. 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. 08/20/2025

    From Silicon Valley to Ukraine Battlefields: Gauthier Vasseur Democratizes AI for 2,000+ Non-Coders

    oin Edward Roske and Gauthier Vasseur as they explore the democratization of AI, bridging the gap between academia and real-world applications. Discover how AI is transforming industries from Silicon Valley boardrooms to Ukrainian resilience efforts. Learn about the power of natural language coding and the importance of asking the right questions in data analytics. Key Topics: AI democratization and its global impact The role of AI in education and business Insights from Ukraine on practical AI deployment The future of AI: Natural language coding and no-code solutions Guest: Gauthier Vasseur, Executive Director of UC Berkeley's Fisher Center for Business Analytics and Co-President of the Alliance for Inclusive AI. Subscribe for more insights on AI and data analytics.  Share this episode with someone who needs to hear it! 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. 08/05/2025

    Why Dave Mitchell Says AI Will Replace Your CFO Before 2026 (And He's Not Wrong)

    In this episode of Asking Good Questions, host Edward Roske engages with finance expert Dave Mitchell, who shares insights from his extensive career spanning traditional accounting to digital media and consulting. They discuss the evolving relationship between technology and finance, the impact of AI on the finance sector, and the importance of trust and judgment in financial roles. Dave also reflects on his global travels and how they have shaped his perspective on finance and leadership. The conversation culminates in advice for future finance leaders, emphasizing the need for expertise and adaptability in a rapidly changing landscape. Takeaways The relationship between technology and finance has evolved significantly over the years.AI is transforming the finance sector, allowing for quicker access to information and analysis.Small companies can now compete at a higher level due to advancements in technology.Traveling globally can provide valuable insights into different business practices and cultures.Trust is essential in finance; over-reliance on technology can erode that trust.The judgment aspect of finance roles is still a human element that AI cannot replace.Future finance leaders should focus on developing expertise in specific areas.Working with entrepreneurs can provide a broader range of experiences and learning opportunities.The finance function is becoming more integrated with other business operations.AI can enhance efficiency but should be used with caution to maintain critical thinking.Sound Bites "Yahoo built the internet, right?""The judgment piece is still human.""Having a specialty makes you valuable."Chapters 00:00 Introduction to Financial Transformation 02:29 The Evolution of Technology in Finance 08:10 Shifts in Finance Perception 10:23 Technology Adoption in Small vs. Large Companies 15:30 Optimizing Resources in Startups 17:51 Global Perspectives on Finance 20:00 Life Lessons from Global Travel 28:08 The Future of Finance and AI 32:19 Disconnecting to Reconnect 34:12 Navigating Career Transitions 39:36 The Role of AI in Leadership 46:16 AI's Impact on Finance 51:30 Reflections on Travel and Culture 55:34 Advice for Future CFOs 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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